Advancement Archives - Page 3 of 12 - How to be Awesome at Your Job

Pete Mockaitis
Kimberly, thanks for joining us here on the How to be Awesome at Your Job podcast.

Kimberly Brown
Thank you so much for having me. Very excited to be here.

Pete Mockaitis
Oh, I’m excited to dig into your wisdom. But, first, I want to hear a little bit about how you’ve studied vocal jazz for 10 years. What’s the story here? And any interesting adventures come from that?

Kimberly Brown
So, definitely, I think growing up, I was a kid who always liked to sing. When people asked me what I wanted to be when I grew up, I said, “Whitney Houston.” That’s what I thought was going to be the career path for me, and I took piano lessons for a bit but I kept on trying to sing. But piano takes a little bit more skill to kind of learn the chords and all those things. My voice clearly was much more advanced than my hands were so I went to vocal lessons. And, oh, my gosh, I absolutely loved it, all the great Ella Fitzgeralds, the Sarah Vaughans. I actually performed a 26-song concert in 2005 to raise money for kids.

Pete Mockaitis

Twenty-six songs.

Kimberly Brown

Yup, I had a pop set and a jazz set. And I say that I’m retired after winning every talent show in undergrad, mind you. I retired. So, now, I only sing for folks who know that I sing. Sadly, it’s more funerals or weddings and things like that. But you can hear me in the shower or in the elevator. There’s great acoustics there too.

Pete Mockaitis
Do you sing in your speaking on stage?

Kimberly Brown
Oh, no. I’m fully retired.

Pete Mockaitis
Okay. Well, so there we are. So, you’ve retired and you’ve moved on into the world of career and leadership development. So, yeah, tell me, when it comes to people and their careers, often you end up working with folks who feel stuck. What leads to people feeling stuck in their careers?

Kimberly Brown
Many times, I really believe it’s not having a plan. If you don’t have a plan to take yourself to the next level, it’s very easy to get stuck in your career. Not knowing what your next move is, not understanding what your own skills and strengths and how those manifests in the workplace, a lot of times people can find themselves being underemployed or unappreciated because they have no idea, they’re essentially treating jobs like old boyfriends or girlfriends, romantic partners, in that they’re just like they keep going on to the next. They get a little bored, they go to the next, they go to the next, hoping that it will get better and better and better and it never really does if you don’t have a plan in place to make strategic career moves.

Pete Mockaitis
Okay. Well, then when it comes to forming that plan, where do you recommend we start?

Kimberly Brown
So, the first stop is really understanding your own skillset and your strengths. I like to have folks who work with me go through a full assessment of all of their strengths, all of their opportunities, all of their weaknesses, their gaps, and really get clear on, “What are the skills that they’ve gained from every single job that they’ve had?” Every single job. That long resume that no one really ever looks at, the one you probably can’t even send to anyone that has every job on there and literally look back and say, “What have you learned? What are your strengths? What are the things you want to continue to use?”

“And what are the things that you no longer want to use? And how can we start to build a career based upon your strengths? And if you don’t have the strengths that you need to get to the next area, what are the things that we need to work on? What are the gaps that we need to attack in order to make your next move?”

Pete Mockaitis
Okay. And so, you mentioned a full assessment. What are some of the key tools or resources or questions or things folks work through to get that picture?

Kimberly Brown
So, the assessment really begins with you. Where are you? What have you done? What are the key skills you’ve gained from all of your jobs? What is the feedback that you’ve consistently been receiving from leaders? And if you don’t have that feedback, we walk through how to get that feedback using a simple start-stop-continue exercise with people in your industry and people who worked with you.

Of course, there are traditional assessments we can do. I’m a big fan of StrengthsFinder or Strengths Profile by Cappfinity. Those are also great as well but I want the baseline to always be the experiences because, generally, where you’ve gained your experiences, how you gained your experiences, what you’re taking away in terms of skill sets and strengths, that’s the baseline for you making your next move. So, the assessment really focuses on where you’ve been and what you’ve learned.

Pete Mockaitis
Now, you talked about how to get that feedback. So, start-stop-continue is a good way to organize the conversation. But how do you recommend folks specifically say, “Hey, tell me what I should start, stop, and continue doing?” Or, how do you recommend approaching that?

Kimberly Brown
So, I always recommend finding time to have career conversations with your management. Many times, folks have one-on-ones, weekly, bi-weekly, monthly, or team meetings, and those are focused on doing the work but career conversations are a little bit different. So, I always recommend that people reach out to their leader, and ask, “Hey, I’d love to have a one-on-one with you but focused on my career.” And ask them simple questions like, “What is it that I should continue to do in my role? What are you seeing as good skill sets that I’m building? What do I need to stop doing? What is going to prevent me from moving to the next level? And what do you need to see more of?”

And the big question I always ask for folks who are thinking about making their next move before it’s time for them to make their next move is the big question of, “What do you need to see from me in order to know that I’m ready to get to the next level, I’m ready to make the next move?” so you’re not asking that question when you’re applying for the new job. You want to ask that question well before it’s time for you to have to apply.

Pete Mockaitis
That is a fine question. And, yeah, as I imagine that scenario, I think there’s probably any number of unsatisfying answers you might get, like, “Oh, you’re great. Just keep doing what you’re doing.”

Kimberly Brown
That’s a fan favorite.

Pete Mockaitis
It’s not quite the right…that’s not helpful.

Kimberly Brown
No, not at all.

Pete Mockaitis
So, how do you recommend pushing or digging a little more?

Kimberly Brown
Now, 100% just like you said, that is the age-old, “Oh, my gosh, you’re fabulous. Things are great. End time.” It’s like, no. If you’re not getting good feedback from your leader, I recommend asking other folks, asking your peers, asking other people who’ve also been promoted, and sharing your experiences so they can share a little bit more insight on what it takes to move to that next level.

And then, also, honestly, having a candid conversation advocating for yourself, like, “Thank you so much. I love hearing that you think I’m doing really, really well. However, I want to make sure that I can be extremely planful, that I actually have a plan. Is there any direct feedback that you’d be able to provide me? Like, what is it that means that I’m doing really well? How do you know that I’m doing really well? What are the indicators for that?”

Or, even if you could call up someone else, like, “I saw that Joe got promoted last year into a similar role. What was it that made you know that Joe was ready?” Try and push back to advocate for yourself just a little bit more because feedback is hard. It’s very hard. Leaders don’t like it, employees don’t like it, so it’s really pushing the needle. And if they say that they need a little bit of time to think about it, make sure you circle back and push again.

Pete Mockaitis
That’s good. And I think that is the perfect response along those lines of, “Oh, you’re great. Just keep doing what you’re doing.” It’s like, “Well, I couldn’t help but notice I wasn’t promoted,” in the nice or professional diplomatic way that you get there because, yeah, those are the realities, is that there is something…well, unless the organization is just broken, which I’ve seen some of. There is something that causes people to move up, “What is it? And am I doing it? And how can I do more of it?” Perfect.

And then you mentioned doing this prior to when you start applying to other jobs because you’re ready to be out of there. What are some of the key indicators that it may, indeed, be appropriate to move on and out from a current role or organization?

Kimberly Brown
So, I’m really big on role mastery and impact. So, when you have essentially mastered your role, when you are doing things with ease, when people are asking for assistance because you know that you have it down, when you’ve built relationships in your role so you have…I always talk about four key relationships that you need. So, you have great peers that you’ve networked with, you have teachers who can help you if you need help, or sometimes people call them coaches, and you have mentors, and you have sponsorships. You have those four key relationships.

If you know where your role fits within an organization, like, “What does your role do?” Every role has a purpose in helping the company reach some type of milestone, even if you feel like it’s a small piece. Like, there’s a reason why that role was hired. Once you really know those things and you could think about, “What is the value you contributed to that role? Have you been able to innovate? Have you been able to move the needle?” Once you’ve been able to do some of those things, then it’s time to start thinking like, “Okay. Well, I think it’s time I start exploring whatever the next move is in this role, whether it’s internal to the company or external.”

Pete Mockaitis
All right. And then if we are looking to transition away, what are some of the most common mistakes you see?

Kimberly Brown
The most common mistakes I see are people relying on the amount of time that they’ve been at the company. Many times, people are like, “Oh, I’ve been here a year,” or, “I’ve been here two years. It’s time for me.” It’s like, “No, there’s people who’ve been in roles for 10 years who still aren’t ready.” The reality is you have to make an impact. You have to articulate value and what you’re going to do moving into that area.

And I’m not sure what your feedback is on what I’m about to say next, but I think that, many times people want to not do a tinge more work to showcase that they’re ready for the next role, especially for folks who are moving internally. They’re a manager, want to be a director. An analyst, want to be a manager. Whatever it is.

But what I explain to folks is that in your role, you’re essentially in a box. Like, this is the role of the manager. You’re doing everything that needs to be done within this box. When you’re ready to move to the next box of the director, you have to showcase that you’re ready to leave that box to go to the next level. And in order to showcase that, you almost have to show people like a little bit. Give them a touch of what they’ll see from you as a director. And it’s important that you start doing a few of those things, making sure that you’re aligning more to a director role than you are to a manager role so people can literally see you in it.

A lot of times, when there’s a job search that’s happening, I used to work in talent acquisition as well, and when you have someone who is internal applying to a job, and you have someone also who’s external, the internal person, you’ve essentially been in the longest interview of your life. They see you every single day. They know you. And if they have questions, like, “Well, why didn’t so-and-so start doing this already? Well, l really don’t see them doing this. They’re doing so well in their current role.”

Versus an external person can come in and just sell them the world because they don’t know them, they’ve never seen their work, and they can easily align to that director role. So, I think it’s really important that when you’re thinking about moving, you start thinking a little bit more on the level you’d like to be on versus the level that you’re currently at.

Pete Mockaitis
Absolutely. And, well, if you wanted my feedback on what you said with regard to doing a touch more work, I think that’s the right answer to advance in your career. But I think it’s also true, what you said is that a lot of people don’t want to do it, yeah, because it’s like, “Well, I’m not getting paid for that. I don’t have the title. It’s like they’re not paying me to do that, so it’s unfair or not justified in the give-and-take relationship between me and employer to do that while being paid what I’m currently paid.”

But what I’ve seen is that frequently your fastest movers and shakers are already doing the next job, and the promotion is kind of a formality, like, “Hey, you’re already doing this. We’d be embarrassed if we didn’t give you the title or the raise, promotion, etc. associated with that.” So, yeah, I think that’s kind of how it shakes out.

Kimberly Brown
Oh, God, I’m happy we’re aligned there because some folks are like, “Nuh-uh, don’t give them a preview till you get the paycheck,” and I’m like, “Nah, you get the paycheck when you give them a preview.”

Pete Mockaitis
Right, yeah. Indeed. And so then, when it comes to the networking world, you’ve got some perspective on identifying power players. Can you tell us how do we find them and build great relationships with them?

Kimberly Brown
So, in every industry, I strongly believe that there are power players. They are people who are at the head of the curve, the people who are the key stakeholders who everyone listens to. There are always a few key people that are great to really look at as sponsors in your network. So, the way I always try to identify them are looking up professional associations. Who’s speaking at the conferences?

If you’re at the conferences, virtual or in person, whose room is packed out every single time? Who is it that has your boss’ ear or your skip leader? Who’s the person who really has the power to make the decisions and you see being frequently called upon? Those are what I call the power players, the people where a business doesn’t happen unless you hear from them first, where they have a significant influence over whatever is happening in the workplace.

When we’re talking about power players, one of the key words there is influence. Same thing with sponsors. They have to be able to influence and impact change. Otherwise, they really aren’t a power player in the industry. So, when you start seeing people speaking at events, or people always tapping that person, you know that person has power in the workplace. And my key is always finding a way to get in the room with them. How can you get as close as possible, again, virtual or in person?

I think you could still do it virtually. In some respects, virtual can even be a little bit easier than trying to navigate yourself into a room in person. But find a way to get in the room. And whether it’s interacting with that individual at the event, even as simple as asking a really great question, or being super active in the virtual chat. Find a way to get involved with that power player and initiate some time, whether it’s a 15-minute meeting to introduce yourself, learn more about them, or attending quite a few events.

If I’m very honest, there are some people who I have relationships with now where it took me years to build a relationship. It wasn’t one time to get on their radar. It was multiple events, multiple things before I reached out and got any individual time with that person. I think, especially when you’re looking for someone who has influence, it’s going to take some time. It’s not going to be a quick one, two, three the first time you try to hear back.

And if you can’t get in touch with that person, I recommend also looking at who’s around them. So, let’s say there is a senior SVP in your workplace and you want to get in touch with them but you know you have not had any luck on getting on their calendar. Well, then who are their direct reports? Let’s see if we can get in contact with them and work your way around, so the next time when you try, you already have some relationships that are close and someone else who can refer you or make an introduction. Sometimes it takes a little bit more time to get that power player.

Pete Mockaitis
Okay. Very good. And so then, so you stick with it and you keep your eyes open. You ask for those recommendations and you’re watching. And then how do you yourself become such a power player?

Kimberly Brown
Again, I think that’s so much about impact and value. It’s about being a subject matter expert, being the SME in your area. Many times, people believe that leaders have to have this big title, they have to be the SVP, the director, the super long title that is confusing, and you can barely say it yourself. But I really believe that everybody has the ability to be a leader.

You are hired for any particular role. That role has tasks and responsibilities. Regardless of your seniority, you need to be the subject matter expert for your role. Nobody needs to do that role better than you are doing that role. You have to lead in that role. When you are leading in your role, so you’ve mastered it, you are the person who they come to for questions or concerns, you have networked yourself appropriately so people also know that you are the best at that role.

You’re not just behind closed doors or in your virtual office, not speaking to anyone. That’s really how you can start positioning yourself as the go-to person and, ultimately, positioning yourself as a leader or the power player in your area. And, also, having that strategy, so knowing what’s next, which means having some of those tough career conversations even if your leader isn’t kind of giving you what you need, making sure that you kind of push forward or find someone else who can give you that feedback.

Having that strategy so you can continuously be evolving your career and moving to the next level, that will slowly but surely be able to position you. And, you know, for some folks, it takes time. For me, even thinking about my own career, for a long time, my goal was to be a director of career services in higher education. I spent nearly 10 years in career services offices working with people at 18 who don’t know what they want to do with their entire life, to people who are in their 60s who want to use all their experience and use that to kind of launch into something that just makes them happy in the world of work.

And I wanted to just be a director of career services running a large office. That was it. And I knew that in order to move to the next level, this wasn’t an arena where I’d be able to stay in one office unless I wanted to stay in one office for like 10 to 15 years to slowly work my way up. So, every two years, I made sure I knew what my next move was, I understood the skills that I needed to gain with each strategic move in order to build a career for myself, and also increase my influence.

I participated in conferences. I spoke at conferences. I always made sure I was able to level up in my career. And, ultimately, I did not get that director of career services job, but I became a director in a global Fortune 100 company in financial services leading some of their diversity talent acquisition recruitment efforts. So, you just have to make sure that you’re continuously leveling up and having a strategy for yourself.

Pete Mockaitis
Well, thanks for sharing your story there. And could you share also the story of someone you think did a fine job of kind of integrating all of these learnings and seen some cool results?

Kimberly Brown
Definitely, success stories. Like, everyone always loves success stories. I have a current client who I was working with who came to me because they were feeling stuck, they’re in one of those jobs that we talked about earlier, Pete, where they were just kind of over it. They felt underemployed, definitely underpaid, and they really wanted to start positioning themselves for leadership roles.

Then when we first started working together, she just wanted to get on track. So, we went through the assessment, we went through kind of understanding all of the skillsets, was she in a career that was aligned to what her goals were. And at that time, she was but she didn’t have the level of seniority that she wanted. She didn’t have the impact that she was looking for.

So, for that particular person, we worked a lot on the relationships. How can we start making sure people know about the work that she’s doing, networking, cultivating some of those sponsors, some of those mentors? And, in about three to six months, I think probably around the five-month mark, if I have my memory serves me right, she’d been applying to jobs and she finally landed a role.

And because she’d done so much work with building relationships, understanding her own personal and professional brand, she rocked this interview process, making sure that she was finally positioned for a role. A lot of it was the language she was using to make sure that she was no longer underemployed and being in a role that was in much better alignment.

She negotiated a $35,000 salary increase. She got added to a committee right away that was aligned with some of her career goals. And she was able to speak a lot about career pathing even in her interview process, so she knew what would be the next step for her, being very candid about looking for longevity in an employer and not just for a defined role.

Pete Mockaitis
Beautiful. Well, thank you.

Kimberly Brown
No problem.

Pete Mockaitis
Well, Kimberly, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Kimberly Brown
No, I think this is good. I think you had me cover it all. I love how actionable all of our questions are.

Pete Mockaitis
Thank you. Well, now could you share with us a favorite quote, something you find inspiring?

Kimberly Brown
Yes. So, there’s a quote by India Arie. It is, “The only thing constant in this world is change.” I put it in my high school yearbook, and I think it’s so, so, so true.

Pete Mockaitis
And do you have a favorite study or experiment or bit of research?

Kimberly Brown
I really like the research on diversity, equity, and inclusion when it comes to privilege. I’ve been doing a lot of research on that, kind of looking into more of the privilege walks. I know Drexel has a lot of information on that arena.

Pete Mockaitis
All right. And a favorite book?

Kimberly Brown
So, my new favorite book is Winning is Everything by Tim S. Grover.

Pete Mockaitis
All right. And a favorite tool, something you use to be awesome at your job?

Kimberly Brown
I think StrengthsFinder, the assessment, is one of my favorites. It helps you understand yourself.

Pete Mockaitis
And a favorite habit?

Kimberly Brown
I live and die by a planner and a task-list system that I use. I have it every day.

Pete Mockaitis
Well, I’m now intrigued. What’s the system?

Kimberly Brown
So, I use Asana but better than that, I really do it in my notebook every single day. I prioritize my tasks by functional area, and for my business, by revenue impact in order of importance. I have a little color code system too. I’ll have to take a screenshot for you, but it helps me knock out even more every single day by having all those priorities in line and make sure that I’m working on what actually needs to get done versus the mini-tasks that we do all day that keep us from doing the big thing that we should be doing.

Pete Mockaitis
And is there a particular nugget that you share that really seems to connect and resonate with folks; they repeat it back to you often?

Kimberly Brown
A lot of it is around confidence. I think I have a quote from my business, my manifesto that I always share. It’s, “You must believe in yourself and your vision. When you do this, you’ll manifest the life you desire.” And I share this a lot because when we’re trying to make any type of career change, I think the number one thing you have to do before we get into all the strategy pieces is believe that it’s actually possible for you.

And a lot of times, when we start talking about that, people are like, “Oh, my gosh, like that really resonates. Like, I didn’t even think that that was important. Maybe that’s why I haven’t been moving.” It’s, like, you have to believe that whatever you want to do is possible for you.

Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?

Kimberly Brown
I would point them to KimberlyBCummings.com. I’m also on all the social places. So, Instagram and LinkedIn are probably my favorite. LinkedIn, it’s my name, and Instagram is kimbcummings.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Kimberly Brown
Yes. So, shameless plug or not so shameless because you said I can share. But I’m a very brand-new author. So, in June 2021, I wrote a book Next Move, Best Move: Transitioning Into a Career You’ll Love and it is available wherever books are sold. And this is the process to help you put together a two-year career strategy.

Pete Mockaitis
All right. Kimberly, thank you. This has been a treat and I wish you lots of luck in each of your moves.

Kimberly Brown
Thank you so much.

Pete Mockaitis
Daniel, thanks for joining us here on the How to be Awesome at Your Job podcast.

Daniel Scrivner
Thank you so much for having me on, Pete.

Pete Mockaitis
Well, I’m excited to dig into this conversation not the least reason of which because you have the fanciest microphone a guest has ever brought onto the show. Can you tell us the backstory of why you have such a piece of equipment?

Daniel Scrivner
Yeah, sure. So, I actually started recording my own podcast a few months ago and was debating in my mind kind of, as everybody does that cares about audio, what sort of a setup to get. The microphone that I use is the Neumann U 87. And I don’t have a great reason for that. I mean, just the only thing that I would say is, in my life, if there’s something that I enjoy, I never feel bad about buying, going for quality if I know that I’m going to use it for a really long period of time, and this seems fit to that vein.

Pete Mockaitis
I hear you. Okay. Well, I love it. So, I also love your story, so it’s pretty wild in terms of so you went from a dropout experience all the way to becoming a CEO with some exciting adventures in the middle. Can you please tell us the story of your climb and maybe the most compelling lessons along the way? And we’ll have a little back and forth as we do so.

Daniel Scrivner
Oh, sure. And I’ll try to keep it brief and feel free to jump in any time. But, yeah, as you alluded to, I definitely have an unconventional background. But what’s funny is it makes a ton of sense to me, obviously looking in hindsight, but when you said the words “the climb” I don’t know why but I don’t feel like it was really that. I guess that for just a little bit of context, a few things that maybe will help kind of makes sense of my journey is, one, I’ve always been a huge believer that if there’s anything in life you’re excited about, if you care enough about it, if you’re curious enough, you can teach yourself how to get good at almost anything.

So, what that’s I’ve done, and I sorted out my career, I focused on design. Specifically kind of web, digital design. This was back in the early 2000s, I’m a child of the 80s and 90s so I grew up with the internet being a really exciting, cool, new part of my life. And the quick backstory is, growing up, I was never attracted to anything design related. In fact, I hated art classes growing up. I never considered myself a very artistic person. So, how I kind of stumbled into design, as I think about it, is I was getting ready to graduate early from high school, this is going way, way back, I ended up taking a course one summer to get some extra credits, I just thought it would be a nice easy fun course about how to create HTML websites. And back in that point in time, creating websites now is a lot more complicated, back then all you needed to know was HTML.

So, I learned that class and I just got hooked on that I suddenly had the skill where I could take an idea in my mind, be able to use HTML to build it, and then I could tell my friends, “Hey, go and visit this URL,” or, “Hi, go and check this out,” and they could pull it up. And that just seemed like this magical thing to me.

And so, the way I stumbled into design was I started making these websites and thought I was going to be excited to share them with friends, but then nothing ended up looking like something I was proud of. So, it’s that moment where I was like, “I can make something but I want it to be cooler. Like, I care about this thing, I want it to be nice.” And so, that led me to this question of, “Well, what is that?” And, for me, it still is how I think about design as I think a lot shaped by that early experience. But my career now, I’ve been doing design at some level for 15 plus years, I’ve worked at companies like Apple and Square and with a bunch of other interesting cool brands.

But, for me, design is just the intersection of solving really hard technical or business problems and trying to pull it off in a way that you can create something that’s singular. So, ideally, it’s remarkable and that it’s unique and interesting and you’re contributing a new note to the melody but, at the same time, is beautiful and you’re kind of pulling off an artful twist.

Pete Mockaitis
Okay. Well, yeah, why don’t we get the broader view first and then we’ll dig into the details with one exception. Okay, so design, I’m not great at design and it always sort of kind of struck me as something – it’s funny, this show is about how to be awesome at your job and skills learning and growth and development, so I almost feel contradictory saying this. But it almost strikes me as something you’re born with, like you’ve got the designer’s eye, like you’ve got the touch, and I was like, “I don’t think I have it.” So, I always outsource my design and I think I know enough to say, “I don’t like that,” and “I love that.”

Daniel Scrivner
You’re a great client.

Pete Mockaitis
Well, it’s so funny, I love designers, I love working with them because I’ll tell them exactly, sometimes I feel crazy about my feedback, like, “As I behold that image, that part of it makes me feel like a little kid and you’re patronizing me,” and they say, “Oh, thank you. That’s great feedback.” I was like, “Really? Because I feel silly saying that out loud and like you’re going to bite my head off,” but the designer is like, “Oh, perfect. I know just where to go based on what you’ve said.” It’s like, “Great.”

Daniel Scrivner
No, I think that’s really all designers, I think, are looking for a lot of the times is just specific actionable feedback. As an example, one, probably the vaguest piece of feedback that I’ve ever received, and it was while I was at Square, and it was from the CEO Jack Dorsey who was looking at a design I did, and said something along the lines of, like, “It’s not whimsical enough.” And that definitely sent me down a like, “Oh, my God, what does that even mean? Like, what is that? Is it the color? Is it the structure? Is it the…?” I don’t even know. I didn’t even know where to go with that.

Pete Mockaitis
It’s not whimsical. Well, because, oh, man, I think for like corporate design, it’s really easy to be too whimsical real fast, and it’s like, “I don’t trust this, what I’m looking, at all. This spinning helicopter hat.”

Daniel Scrivner
He wanted that dial cranked up and I was scratching my head for a long time.

Pete Mockaitis
So, let’s start there. So, learning design, that seems like a skill that’s hard for people to pick up if they don’t have some kind of aptitude for it but it sounds like you disagree. Lay it on me.

Daniel Scrivner
Yeah, I definitely disagree. So, I think, well, just to take a step back. I have definitely worked with a lot of engineers that have led me to believe that there are certainly some people that probably don’t get design, like don’t understand colors, just kind of don’t understand just aesthetics in general. So, I think you have to have some inclination or curiosity or a desire to do a lot of research to just develop a point of view about like what looks good and what doesn’t and what is that. And that’s something that’s very difficult to build up.

If someone were to ask me, “How do I figure that out?” I would say, “I don’t know. You need to watch a lot of movies, read a lot of books, look at magazines about architecture and car magazines,” because I think that’s one thing that’s always fascinated me about it is great design can work in any industry whether it’s an interior designer using color and shapes and symmetry and patterns and textures to create a beautiful inside of a house, whether it’s an architect using some of those same tools to create a beautiful structure.

What’s interesting about design is kind of, if you boil it down, it is extremely primitive in that it’s largely shapes, colors, tones, moods, so, I definitely believe that anybody can learn it. And I think that, for a little bit of the backstory there, so I’ve mentioned I’ve been doing design at some level for 15 plus years, and every single year I continue to get probably a handful of emails from somebody that saw my work or listened to an interview that I did, who writes in and says something along the lines of like, “I’m inspired by your story. This is something that I want to do. How do I figure this out? How do I start working as a designer?”

And the reply I always write back is probably not the reply they were expecting. In fact, rarely do I ever receive a reply back. But it’s just along the lines of, “Like, the way I was able to do that,” so if someone kind of understands my story and knows that I dropped out of college so I don’t have a college degree, I did that because I found in this thing that I loved and I didn’t want to put that off anymore.

But the way that I learned it was extremely basic and probably it’s just like hustle applied to trying to learn. But, for me, it was very much like, “I want to do this thing,” so my approach was just, “Okay. Well, I’m going to do free work to start,” so I literally got paid nothing when I first started, and I was going to, honestly, anybody I knew or anybody that knew somebody that I knew that wanted something designed, and typically that would be a business card or a logo or a website, and I would just do it for free because I knew that I wanted to be doing it, I needed to have a portfolio so I can get better work, land better clients, eventually start paying. And so, I really just worked my way up that way from literally the lowest level on the totem pole of doing free design work for people that I just knew, all the way to working for some of the largest companies and most respected brands in the world. But it very much was a, “I’m just going to take it one step at a time.”

And, for me, one thing that ties back to, which we can certainly explore, is something that’s played a big role in my life is what I refer to, what I call the growth curve. And, for me, it’s just the sense that I think the way I’ve been able to get to where I am today is by constantly trying to challenge myself. And I’ve done that multiple times in my career where I’ve left really comfortable jobs, not because I wasn’t excited about that work anymore, I was still very excited about the work I was doing at those companies, but because I felt like I needed a new challenge.

And I don’t really know, I sort of know where that comes from, but there’s something in me that once I’ve kind of figured something out, I get a little bit uncomfortable and restless. And so, I’m always trying to challenge myself and kind of climb this growth curve.

Pete Mockaitis
All right. Well, so there’s a lot in there right there in terms of going out and doing it and getting a lot of reps. It sounds like whether that’s doing your own work or observing other work. And I found, I think, it is interesting with design in that I think it’s taken me a while to get here and not that I’m a pro by any means but it really is, for me, it’s kind of uncomfortable for a while, it’s like, “I just need to kind of…” I feel it first and then I had to articulate it in terms of, “Being in this room feels awesome. I love it here.” It’s like, “Why?”

Pete Mockaitis
But then you start to get a few things. In, like, realtors, like they’re taking photographs of places, it’s like, “The top thing is it’s free of cluttered garbage.”

Daniel Scrivner
“It’s bright. It’s airy. It’s typically lots of light, lots of very clean white and stainless steel.”

Pete Mockaitis
“And there’s just not a lot of clutter.” And I think that’s huge right there in terms of…and that can apply to a space or to a layout or a website or whatever. Like, I think Oli Gardner, I heard on an Unbounce event, had a slide wherein someone was like begging like Oliver Twist, “Please, sir, one more link shoved into this website.” It is like, “No, you got to keep it focused.”

Okay, so by doing a large volume of work, and by pushing and challenging yourself, and by observing and reflecting, you got really good at this skill. So, the here we are in your story.

Daniel Scrivner
Over a long period of time.

Pete Mockaitis
So, now you’re great at design and you have made some stuff that looks good, and where does this story go next?

Daniel Scrivner
Yeah, so maybe that was the kind of first formative part of my career, and I think for me there was a moment in time that I still remember very vividly but at the time didn’t feel…honestly felt scary and I don’t know if I was optimistic but I was excited about it but, basically, to share a little bit of the story. So, I’m in high school, I take this class, I start doing work for free, literally, when I’m in high school, end up graduating six months early. A big reason why I did that was I just wanted to do more time doing design work and I felt like, “Why spend all my day in school if I can kind do more of this work that I really enjoy?”

So, I graduated six months early. Fast forward a couple of years, and I’m suddenly at the point in my early 20s at this point in time, probably 21, something like that, say, and I suddenly have this kind of fork-in-the-road experience where I’m in college at the time, I’m about to finish my undergraduate degree, getting ready to kind of pick and transfer to the university that I want to go to which, in my mind, is kind of my parents’ voices. They were always very much, “You have to kind of go through this order,” and one of those things that was non-negotiable was going to college, so I was like, “Okay.” And I know that’s what I should do or that’s what felt like what I should do.

But the other thing I had in the other hand was, at this point, I had done enough design work that I actually was getting paid to do it, and was really enjoying it, and had enough work that I actually had to turn down projects. And so, the fork-in-the-road moment was, “Do I continue with college, kind of go to a university, really focus on that experience for the next two years or do I decide to take a bet on myself?” And at that point in time, the way I was framing it, which was probably a little bit nice, is kind of pause school for six months. I ended up quitting the job that I had at the time so I kind of severed all of those things so I could go all in. And my only goal was, “Let me see if I can survive basically doing everything by myself.”

So, I would pitch clients, I would quote clients, I would give them estimates, I would do the design work obviously, hand off the designs, do all the kind of the clerical stuff and accounting stuff. I just did everything. In those six months, I ended up doing that. Initially, my goal was just to make it six months. I ended up making it six months and it wasn’t pretty. A lot of that was extremely challenging, it was extremely difficult, it wasn’t all stuff I was super excited about. Balancing books or collecting invoices or following up on payments is not the most exciting thing in the world compared to design, but I ended up doing that.

And what that ultimately led to was, fast forward another year past that, I ended up getting offered a job to go and work for an advertising agency in L.A. called DDB. That led, about a year and a half after that, to getting offered a job at Apple to join their marketing communications team which was when I moved to San Francisco, and I ended up being at Apple for three and a half years. And I credit that a lot with being my…if there was any real-world bootcamp-like education experience in my career, it was absolutely being a designer at Apple.

Pete Mockaitis
Okay. Well, so let’s zero in on these particular bridges, leaps, transitions to DDB and to Apple. How did they find you and interview you, etc.? Was it just like, “Your stuff looks good, come on down”?

Daniel Scrivner
It’s effectively that’s the gist but the DDB, to be super honest, I have no clue. I cannot remember if they found me, if I found them, I’d never really heard of the firm before so it’s made me think.

Pete Mockaitis
Oh, they’re huge.

Daniel Scrivner
They’re a big advertising agency but they’re not Ogilvy. They don’t have that kind of brand name recognition necessarily so that one I’m not sure.

The Apple one is, I think, a little bit more interesting. So, the Apple one was, at this point, I was, I don’t know, mid-20s, probably 25, something like that, 26, and I, for sure, obviously, Apple was an incredibly exciting company, and I think for a lot of designers, it’s the place you hope you can get to at some point in your career. And so, the way that kind of transpired for me is I have this job at DDB at the time in L.A. so I’m commuting to L.A. and I’m doing all that and I’m enjoying my work. It’s not the most exciting. I’m not doing the most challenging interesting modern stuff but I’m doing it. I’m an actual designer getting paid to do design work which is crazy.

And I end up getting an email from a recruiter at Apple. And for those that don’t know, Apple is definitely one of the companies that they have a large recruiting team, and their recruiting team, they really are looking for the best of the best or people that they feel like can succeed as designers in some department at Apple. And for people that don’t know as well, Apple is massive. Even in the marketing communications team, I joined as a marketing designer, I worked on a lot of Apple.com projects, I ended up getting to do a lot more interesting stuff kind of in my time there.

But Apple also has motion graphics designers which just do things like animations and transitions and videos. They have graphic designers which do the packaging and the identities for some of their products. If you look at like AirPods Pro, like that name on the box, that’s something that a graphic designer put together letter by letter, playing with the kerning, playing with the weight, trying to get that just right, so it’s a huge department.

So, to kind of get back to the story, my first thought, honestly, was this is spam. Like, “Let me see where this email is from. Let’s me see if it’s actually from Apple.com.” So, I end up looking at it a little bit, kind of looked up the name of the person who sent it, and it all checks out. And the way that worked initially was I was offered an opportunity to come to Apple and cover for a woman who was going on maternity leave for six months, so it wasn’t like, “Here you go, here’s a full-time offer.” It was, “We really like your work. We would like to have you on the team to start,” and this is also very common at Apple about, I would say, probably 50% of the creative team is all contractors so it’s not full-time employees, so that’s not uncommon.

But I came in on contract and kind of my approach was, “I’m going to soak up everything I can, learn everything I can in these six months, and I’m also going to try to prove that I have a place on this team, that I can contribute and I can be a good designer and a good kind of member on the team,” that’s a little bit of that story.

Pete Mockaitis
Okay. And so, recruiter. I’m curious, in both of these instances, did they just not care, like it doesn’t matter in the design world, or for you in particular, “Oh, you don’t have a degree? No problem”?

Daniel Scrivner
So, it’s really interesting. I would say, for both designers and engineers, number one, I think there are a lot of technology companies, it’s definitely not a deal-breaker. Like, I think Google, they’ve relaxed this policy, but Google is definitely out of the norm in their requirement, which I’m not sure if they have anymore, but they have had for a very long time, is a requirement that you can’t get hired unless you have some sort of a college degree. But, typically, at technology companies and at startups, it doesn’t matter.

And the way that I’ve always thought about it is the majority of designers I’ve worked with do not have a design degree, and I think that’s part of the problem is if you were to try to go get a design degree, you can get one but it’s what is typically called a Masters in Fine Arts. You’re going to be doing it for six years, you’re going to learn all these kinds of fundamental skills, which I would argue you could learn just as well on your own by teaching yourself because it’s just literally going in kind of design history, looking up work of famous designers, doing these mock projects.

And part of that was, the way that I thought about it was, because if we go back to the part of my story where I was deciding whether to go to college or whether to take this kind of six-month bet on myself, definitely in the back of my mind was, like, “I can go and study design,” but the sense that I had was I was going to be learning fake design. So, part of what you do if you go to a Masters of Fine Arts program is kind of like going to business school, and you do a bunch of case studies, which are perfectly fine. They definitely help exercise some of your mental muscles of like, “Here’s a problem. How do you figure it out?” But does it map to the real-world job of being a designer? Absolutely not.

The most difficult things involved in kind of being a designer at any level is stuff like, “How do you gracefully take feedback that you agree with or don’t agree with? How do you ask really great questions of another person’s work where you don’t want to offend them, you want to know and respect that they put a lot of work and energy and love into what they’re creating?” But you want to try to ask great questions to kind of spur and make sure that it’s as good as it can be. And so, there are all these skills in design that are largely very powerful but very soft skills. And the only way you can really learn them is by doing it.

And so, that was kind of my perspective at the time. And what’s been interesting is I’ve had the opportunity to work with quite a few people that have a Masters in Fine Arts degree, and I don’t say this out of disrespect for any of those people, it takes, obviously, a huge amount of hard work to go and get a Masters in Fine Arts degree. But did I think they were necessarily better day in, day out designers? No. And I think, typically, they would have kind of a chip on their shoulder a little bit of, “Well, this project is too good for me.” And I think part of what helped me was there was no project that was too good or not good enough for me. Like, I was excited to work on it and take it on if it was a design challenge. And I also just loved it and I think that there’s this kind of sense of enthusiasm and love that, I don’t know, maybe I didn’t get it beat out of me in college but I was lucky that way.

Pete Mockaitis
And that’s a great perspective when you’re at Apple, it’s like, “I’m going to learn as much as possible in this place,” and in so doing your skills are sharpened. And so, what happens next?

Daniel Scrivner
So, I ended up at the end of those six months, I got offered a full-time position and I joined the Apple marketing they called it. I don’t know what’s called anymore but they called it MarCom internally which was short for marketing communications. But, basically, at the end of the day it’s like everything that’s not an ad on TV, that team did it.

So, I ended up getting offered a full-time position. Fast forward a little bit, about three years later, I found myself in a position I found myself in a few times now where when I first got offered the opportunity to join Apple, I thought, “Oh, my God, this is it. This is the place I’ve wanted to be. I can’t wait to be on this team.” And three and a half years later, again, really, like for me, I think a word that sums up a lot of how I approach the things that I love, which is both good and bad, but I think largely good is obsessive. And so, for me, with design, I just obsess over it. I would think about it all the time, I would constantly be working on little projects to try to improve my skills.

So, one of the things that I would always do when I was at Apple, and I think this is great advice for anybody that has a job, where it’s like you’re going to get better the more you do it. And if you challenge yourself with things that are slightly out of your comfort zone, you’re going to show up to work just a better all-around employee. But I would do things like, when I first joined…I knew how to put together a layout. In a layout, you can sometimes describe that as like if you go to, I don’t know, Apple.com, a layout is “What generally does this page look like? How do you chunk it out? What’s the typography there? Where are kind of the images?” It’s very similar to doing product design if you’re doing a layout for a screen.

So, I could do that but I suck at doing icons, and icons are this thing that they are like if you go and you open up your iPhone, if you have one, or Android phone, if you don’t, you look at kind of the app icons or the little graphics or symbols that you click on to get around an app, that’s icon design, and it’s both a very ancient form of communication. It’s based on hieroglyphs and cave paintings, and there’s a lot of those things that map almost literally one-to-one for kind of icons that we have today. So, it’s a very old form of kind of communications but I was really bad at it.

And so, one of the things I would do is just challenge myself, like, “I’m going to make an icon set of 30 icons I’m excited about.” And the way these projects always go is they’re absolutely brutal in that for 80% of the time I’m just like, “Oh, God, I’m not getting any better. What’s going on here?” And I just keep chugging through and trying to put one foot in front of the other again and again and again. And, inevitably, what happens is if I can just persist long enough, I’ll finally get to a place where it all snaps into place. So, I would do stuff like that.

But about three and a half years in, I just had this moment where I felt like I knew how to be successful at Apple. And what I mean by that, and hopefully it doesn’t sound egotistical, but in my mind, if you kind of take a step back and think of a place like Apple, they have a very recognizable aesthetic. Well, what does that mean? That means that there are rules that inform it and that there’s kind of like a construct and a framework for how they think about it. And so, if you can understand those things and get good at those, you can take on almost any project and figure out end time how to execute it in an Apple way.

And so, I’ve kind of gotten to that point and I had this moment where, again, I did this kind of flash forward, saw myself at Apple 10 years in the future, and thought that that would’ve been perfectly fine. And there are still times when I think back and wished that maybe I’d stayed a little bit longer just because there were such incredible people there and I learned so much and just enjoyed working with them, but I felt like that probably wasn’t the best thing for me. And part of what inspired me in that was, what I alluded to earlier, Apple has a lot of contract designers, and typically those contract designers, they don’t work at one company for longer than six months.

And one thing I observed that I thought was really interesting and different about the best of these contract designers were that when they were teed up a problem, they could look at it from ten different angles. And so, they could say, “Okay, I know,” as an example, say, something like take an example that came out today. So, Apple announced these AirPod Max, like headsets that you put on your head that literally are like headphones. And so, you would get teed up a project, like, “Hey, here’s this thing we’re going to launch soon. Figure out how to tell this story on a marketing website.” And you need to think that through.

But what I found fascinating about the people who had kind of a broad body of experience was they could look at it from a bunch of different angles. They could do a dark version of that layout, a light version of that layout. They could do something that felt super pop culture-y. They could do something that felt really minimal and restrained, and I thought that there was something really special there. And so, the kind of story I put together in my mind was, “Okay. Well, I think part of that is they just get to flex different muscles. They’re constantly taking on different challenges.”

And so, what that led me to think about was rather than stay at Apple, which would’ve been perfectly fine and would’ve been a great outcome, but rather than doing that, I think it’s time for me to challenge myself. And so, what I ended up doing, which was not at all common at the time, was leaving Apple, which when I was there no one left Apple. You didn’t leave Apple to go work somewhere else especially as a designer, and you definitely didn’t go to a startup, but I decided that I wanted to go and join Square. And Square, at that time, was about 50 people in size, it was in San Francisco, it was right in the city, I didn’t have commute, so that’s why I made that leap.

Pete Mockaitis
Very cool. Well, I want to push fast forward a little bit. So, you went to Square, you did some great things, and now you’re the CEO of Flow. How did that come to be? And what is Flow?

Daniel Scrivner
Great question. So, yeah, I guess I’m trying to figure out how to back it into this question. So, if we go back a little bit in my story when I was really young, one of the things I talk about was just this belief that if you are interested in something that you could figure out how to do that. And I give a tremendous amount of credit to my parents. So, growing up, we would do things like it was very common, probably happened once a month where we would all get in the car, drive down to the biggest library nearby, spend hours and hours in a library.

And so, one of the things that I got, I have two younger brothers, we would all, literally all five of us, we’re a five-person family, we would split out, all go to different levels, find the books that we were interested in, and we would spend hours there. And at that point in time, we were kind of young, say, 10, 11, 12 kind of age. And so, one thing I got fascinated, just hooked on, that I can’t really still put my finger on it, and say, “Why?” was business and investing.

And so, in high school, I was reading books like The Millionaire Next Door, or, Rich Dad, Poor Dad, or, I can’t think of other ones, but like largely business and investing books that typically people aren’t interested in let alone in high school. I’ve just always been fascinated by that, and that’s something that still, today, I’m always…it’s another obsession I have, is I just love learning from investors. Why? Because I think they’re experts at kind of thinking through industries and companies and which company has the best odds to success and why. And I’m also really fascinated with entrepreneurs, and this is the idea of creating something of value that you end up charging more for than it takes to create, which still, to me, feels like kind of pulling off a magic trick that someone is willing to pay for that even though it costs less to make it. It generates profit and you can invest that in other things, so I have these interests.

So, fast forward, I end up leaving Square after five and a half years. At that point, the company had IPO’s, we were 1,500, probably 2,000 plus people at that time, had an incredible experience. But for anyone that doesn’t know, being at a company that goes from 50 people to 1,500 or 2,000, and from having a little bit of venture capital money all the way to IPO in five years, it is a brutal experience. It’s wonderful in so many ways but it is also an incredibly trying and difficult experience.

So, I got to the end of that, was super proud of what I had done when I was at Square, and the team that I was able to work with and helped build, but I knew, again, that I wanted to flex some different muscles. And so, what I did leaving Square was I started kind of exploring things that was entrepreneurial-like and investor-like, so I did. I started doing some venture capital investing, some seed investing in companies. I now have a portfolio of over a hundred that I’ve built up and I’ve learned a lot from that. I also started advising companies. One thing in San Francisco that, this is maybe changing today, you know, San Francisco is changing quite a bit at the moment with the coronavirus and just all the effects that that city is feeling.

But at the time I was there, it’s just packed with people that are really good at what they do, they have really interesting ideas. And so, what that means is there are a lot of startups that don’t get design but need design to be successful. And so, I started working with some of those to help them think about how to think about design on their side.

Fast forward a few more years, and I ended up…so Flow is owned by a company in Canada called Tiny. And Tiny is like a mini conglomerate. You can kind of think of it like a mini-Berkshire Hathaway. And I knew one of those founders, Andrew Wilkinson, for about 10 years, and this was going back, it’s like very serendipitous, but going back to being a designer early on. It’s a really small community. So, we kept in touch and kind of he was a designer, I was a designer, we would both kind of check out each other’s work and loosely stay in touch. Long story short, fast forward a bunch of years in the future, and he now has this company that has many sub-companies, Flow is one of them.

And so, for a little context about what Flow is. Flow, at this point in time, it’s a 10-year-old company. We focus on task and project management, software, largely for teams. And the way we excel, the way we kind of compete is by offering people a beautifully made product that is powerful but it doesn’t feel bloated and it feels like something you’re excited to work in. And the metaphor I use there a lot of the times is like WeWork office versus a cubicle. And if you think about productivity software, a lot of productivity software is the cubicle land, and we try to create this beautifully crafted piece of software that teams need.

So, we went to grab coffee. Flow, at that point in time, was not doing super well and they felt like they wanted somebody to come in and take over and someone ideally with design background that could kind of invest a ton in the product, create a vision for the product of where it was going to go from there. And so, I joined Flow two years ago, and over the last two years, I’ve been working on turning around the company.

Pete Mockaitis
All right. Well, what a beautiful tale from making websites to you are heading up a company and are investing in businesses that are really cool. By the way, I use Superhuman for my email and I love it.

Daniel Scrivner
I love that.

Pete Mockaitis
So, wow, so what a journey. I’m drawing my own little lessons about really digging deep and then challenging yourself and learning from the people around you and keeping those relationships alive. But since we’re actually towards our final minutes here, why don’t you boil it down for us in terms of what do you think are the top do’s and don’ts for professionals looking to grow a career and advance in, hey, more fun wins, meaning in money, as we say here? If you want more of that over the long arc of your career from age 20 to age 60, 70, top do’s and don’ts, lay it on us.

Daniel Scrivner
I could probably talk about this for an hour so I’ll try to be as concise as possible just because I think there’s so many…like, one thing I think you’ll learn over time by working in a lot of different companies, by being at different stages of your life at different companies, it’s a very nuanced thing. So, I will share, I think, what’s helped me and people can decide whether that’s useful. But I think the big things for me is, ideally, you’re doing something that meets that bar of obsession. Like, in my mind, I’ve got a two-year old now, we’ve got another one coming on the way this right around Christmas, and with my kids, I think, the focus there is very much I just want them to find something that is energy-giving and life-sustaining. And I think if you can do that, then you have this…it’s almost like a nuclear fusion reactor where you have something that is just never going to run out of juice.

The goal, in my mind, initially was I wanted to find a couple of things, and at this point in time, that’s design, business, and investing, that I can think about, obsess about, read about, and try to get better at over the long course of my life. And so, find those things and then pour yourself into them. And what I mean by that is I highly encourage people, and again life is a single-player game, you have to decide if this is applicable for you. But, for me, something that’s always been really helpful is you find that thing that you love, then pour yourself into it. And what that means is not only giving 100% at work but, ideally, also doing stuff outside of work that challenges yourself and develops muscles that are probably related to what you at work but might help you prepare you for your next job, might help you prepare for the job you want five years or ten years, or what you want to be doing.

And I think back to my time at Apple, and I would work a full 10-, 12-hour day, get on the bus, do this fun little icon project. I didn’t do it every day. There were definitely days I was burnout or I just needed to shut off my brain but I’ve always had stuff like that going on the side. And I think people have different opinions about that. In my mind, I do the things that I love, and so what that means is there’s very little distinction between work and play, or work and real life. And so, I think that blurriness is really helpful.

And then I think another thing that I would suggest is to challenge yourself. Like, something that I have distinctly found is that the majority of people I’ve worked with are kind of limit their own trajectory by the belief they’re willing to have in themselves, the confidence they’re willing to have that they can overcome any hurdle, and just this deep sense that if they’re interested enough in something, if they want something bad enough, they can figure it out and they can do it.

And this isn’t a anything-in-the-world-you-can-have-go-for-it type kind of pep rally or speech. It’s just I think the way to kind of think about it is this very soft, just in the background confidence of if there’s a challenge that you see in front of you, believe in yourself, bet on yourself, and know that if you just keep putting one foot in front of the other, and you can find a way to push through discomfort, that there are really good things on the other side of that.

And then the other thing I would say is really throw yourself into that growth curve. I almost try to visualize it in my mind of I always want to be in a place where I’m pretty uncomfortable. Ideally, if I’m in a job or doing something and I’m committed to it, I’m really excited about it, I want it to be slightly out of my comfort zone. And I think this role that I’ve taken on with Flow is certainly that. The role I took on early on at Square was certainly that. When I was at Apple, it was certainly that. And I think if you string together kind of subsequent experiences that step, by step, by step, challenge you a little bit more, get you a little bit out of your comfort zone, make you do things that you don’t feel like you’re qualified for or you don’t think you can really do yet, I think the trick there is like a lot of people have this idea that, “I’ll do that once I can do it.”

And if that’s the way you think about it, you’re never going to do it. You just have to start doing, be willing to be bad at it, be willing to be uncomfortable, be willing to kind of cringe even at the quality of your work initially because that’s the price you have to pay in order to get better.

Pete Mockaitis
Well-said. Thank you. Well, now, could you share with us a favorite book, something that you really dig?

Daniel Scrivner
Yeah. The book I was thinking about kind of before this interview that I think might be really applicable, maybe people haven’t heard of, that I really enjoy is a book called Principles by Ray Dalio.

And for a little bit of background there, Ray is the founder of a hedge fund called Bridgewater, it’s the largest in the world, they have a very different culture where they really try to go all in on this idea of meritocracy which is that there’s not really any hierarchy; it’s just kind of a group of peers, and anybody is as good as anybody else and it’s all about kind of the arguments you can make and the work that you’re able to do.

And so, that book is the output of the last 30 plus years of trying to build this company, and it really is what’s in the title. It’s a handful of principles that apply to working in groups and working as an individual. And I’ll stop there, I won’t spoil it, but it’s a thick book. I highly recommend you get the hardcover just so you can open it up and flip through it. You do not need to read it from cover to cover but it is an incredible work.

Pete Mockaitis
And a favorite habit?

Daniel Scrivner
So, something I’ve been thinking a lot about, and this falls into the vein of like, “I’m not good at this yet, but I see the value in it and I want to double down on it,” is taking time to reflect each week. And this is something that I think, if I were to go back in time, this idea of reflection and what does that even mean, where you’re kind of pausing, you’re not doing any work, you’re going to stop sprinting, you’re going to stop focusing on your to-do list, you’re going to stop caring about your email, you’re just going to stop. Ideally, go somewhere where you can kind of think by yourself and sit down, and just really reflect on how things are going at the moment.

And, for me, I try to do that once a week for at least an hour. I have somewhat of a structure, I’ve a few questions I ask myself every single time. Some of those are really simply things but these are, at the end of the day, really profound questions, like, “Are there opportunities that are around me, or I have access to, or I see that maybe I just haven’t recognized?” And, especially in my role now, that’s true all the time.

Another one is, “Are there risks I haven’t recognized? How are things going? What’s going well and what’s not?” But I think taking time to reflect, the kind of metaphor I would have with that is, I think, reflection is something that almost none of us do often enough. The reason it’s important is because anytime in your life that you have a goal, you need to be able to know how you’re tracking and course-correct. And what I found in my own life is I would reflect once a year, maybe by doing New Year’s resolutions, or once a month, or once every six months, and that’s okay. But I think if you can get that down to where you’re spending a little bit of time, it can even be 20 minutes or 15 minutes once a week, what it allows you to do is it just tighten up and kind of keep you on track with where you’re headed. So, I would say reflection is big.

Pete Mockaitis
And if folks want to learn more or get in touch with you, where would you point them?

Daniel Scrivner
They can visit my website to see the podcast episodes I record, to see the stuff that I write at DanielScrivner.com. You can also follow me on Twitter @DanielScrivner and they can learn a little bit more about my podcast if they’re interested at Outliers.fm, and about Flow at Getflow.com.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Daniel Scrivner
I call it kind of the alpha challenge but one thing that I have written on a Post-It that’s a little bit trite but I find it really helpful is just, “If you weren’t afraid of the consequences, what’s something that you would try that you likely wouldn’t try otherwise?” And so, I think asking yourself that question, really thinking about that and being open with what that answer is, bring that whatever answer you write down, you have to give yourself permission, you have to believe in yourself that you can go and figure that out, and you can go and do it.

And so, I would challenge people to ask themselves that question, “What’s something that you would want to do that if you didn’t care about the consequences and weren’t looking at feeling or any of that stuff?” and take that answer and bet on yourself and figure out where to take that.

Pete Mockaitis
Daniel, this has been such a treat. I wish you lots of luck with Flow and your challenges and all you’re up to.

Daniel Scrivner
Thank you so much, Pete. It’s been awesome.