875: How to Unapologetically Ask for What You Want with Jenny Wood

Pete Mockaitis
Jenny, welcome to How to be Awesome at Your Job.

Jenny Wood
Thanks so much. It’s great to be here, Pete.

Pete Mockaitis
Well, I’m excited to hear about some of the wisdom you’ve gathered from your time rocking and rolling on your career program at Google and your upcoming book, The Chase: Unconventional, Uninhibited, and Unapologetic Guide to Getting What You Really Want in Life. That sounds pretty handy.

Jenny Wood
Well, I hope it will be handy. I think we over-apologize in life, right? We say, “Sorry. Sorry, I’m late,” instead of, “Thanks for your patience.” I’m not saying that we should never apologize but I think that sometimes we over-apologize when we really are just trying to get what we want in life.

Pete Mockaitis
That’s true. And you’ve got a cool story about meeting your husband, unapologetically. How did this go down?

Jenny Wood
Yeah. So, let me paint the picture here that I tend to have a bit of anxious tendencies. I tend to be pretty data-driven. And when I was single and dating in New York City, I now live in Boulder, but back in 2011, I was single and dating in New York City, and I was riding the subway home from work one day, and I saw an attractive guy standing about 30 feet away from me.

So, my natural somewhat anxious data-driven tendencies would have me sit there in my seat and say, “Well, there’s nothing to do about this. I’m not going to go up and strike up a conversation with him and have all these people look at me while I’m doing that.” But then as the doors were closing, when he got off the train, something took over me, something pushed me out of my subway seat and gave me the courage and the confidence to chase after him, hence the name of the book, The Chase.

And so, I caught up with him, I tapped him on the shoulder, I said, “Excuse me. I’m sorry to bother you,” and he said, “That’s okay. You seem nice.” I gave him my business card, and we went out on a date a week later, and the rest is history. He’s now my husband, my incredible partner, the father of my eight- and five-year-old son and daughter. And that was because I decided to simply ask for what I wanted that day.

I got a little bit curious about what might happen if I was bold, and I got over those anxious tendencies that were keeping me small. And the worst thing that could’ve happened that day was he could’ve said, “Sorry, I’m married.” And then I have my answer, which was better than not knowing to me, because living in uncertainty is so hard. And it’s win-win because then he gets to go home to his wife and kids, and be like, “I still got it, honey. I got hit on the subway.”

Pete Mockaitis
That is beautiful in terms of that’s still a benefit to both of you in terms of you can feel confident and proud of who you were in that moment, and rising and being courageous, and he can feel complimented. But I’d like to zoom in when you said, “Excuse me, I’m sorry to bother you,” what was, if you can recall, as much of the verbatim exchange as possible? Could you share that with us?

Jenny Wood
Yeah, and it’s a little ironic because I started off by saying part of my platform is stop apologizing and I did say, literally, “Excuse me, I’m sorry to bother you.” So, I guess that was before I had evolved into this thought leadership train that I now get so excited about. But he literally said, “That’s okay. You seem nice.” I was carrying flowers from an acapella rehearsal because Google has all sorts of fun activities and things you can participate in, in addition to your core job.

So, I was carrying flowers that were left over from this acapella rehearsal, and I was holding these white Gerber daisies, so he thought I was trying to sell him flowers. And then I said that I was interested in going on a date with him, and then that’s how it happened.

Pete Mockaitis
Okay. Lovely. That’s really cool. All right. Well, so you have an interesting vantage point. You’ve seen a lot of people chasing stuff and interested in things, working in career development and other fields, and putting together some of these tidbits in your book, The Chase. So, can you share with us, any particularly noteworthy or surprising or counterintuitive discoveries you’ve made about us humans when we’re chasing stuff?

Jenny Wood
Well, honestly, some of it is unsurprising, which is we could all use a little bit more confidence in life. I would even take this as far as finding your swagger, or maybe even being a little less shameful, which you might flip and call shameless, which has a very…

Pete Mockaitis
Oh, there’s the show, yeah.

Jenny Wood
Yeah, there’s a connotation there, right?

Pete Mockaitis
You don’t want to be that vibe.

Jenny Wood
Well, I think what we want to do is to get rid of all the shame that comes, that gets in the way with us going after what we really want. So, for example, oftentimes, we’ll be at, let’s say, a PTO meeting or at a meeting at work, and someone says, “Well, this is a shameless plug.” Actually, my job before Google, I was sitting in this meeting, and someone said, “This is a shameless plug,” and then they began to share a spreadsheet that was going to be so useful to the other 20 people in the room, and everybody said, “Wow, this is going to save me time. This is going to make me so much efficient.”

And so, rather than this person offering, as a lead, “And this is a shameless plug,” perhaps they could’ve said, “This is something that I created that might be useful and helpful to all of you.” So, what I find to be unsurprising is that a lot of us feel impostor syndrome. There was a study out of the University of Glasgow that said 75% of employees regularly feel a lack of confidence at work.

And you think of all the hard stuff that’s going on, we’re just coming out of the pandemic, there’s economic uncertainty, we have new ways of working, there’s headwinds in a lot of industries right now. And as we face all these headwinds, it’s unsurprising that we have additional impostor syndrome or a lack of confidence.

But by finding your swagger, by building your confidence, by asking for what you want, unapologetically, or offering a room of 20 people a useful tool that will save them time and make them more efficient is a way to find your swagger, is a way to increase your confidence, and to stem your impostor syndrome. And one way I think about this, one practical tool, is to know your superpowers, which I’m happy to go into, Pete, or we can take this another direction.

Pete Mockaitis
Yeah, knowing superpowers is awesome. That’s come up a couple of times. And as I’ve heard it described, some people will call it like a spike. It’s not just people skills or problem solving, but rather it tends to be much more specific and precise and nuanced. So, can you give us, first, some examples and then share with us, how do we uncover that?

Jenny Wood
Yeah, so my three superpowers are leadership, influencing people, and building things from startup to scale. And it took me narrowing down a number of things that I feel like I’m pretty good at, and narrowing it down to three, but it also took me expanding from zero on those days where I feel like everybody is smarter than I am, everybody is more talented than I am, everybody knows more about the industry, the product, the process than I do.

And by knowing my three and having them practiced, I have them ready to roll off my tongue in any situation. That could be a meeting with a perspective mentor. It could be a conversation with my manager. It could be a coffee chat with a new friend when I moved to a new city, which I did when I moved from Manhattan to Boulder in 2018.

So, I always say this about my second superpower, which is influencing people. At the end of the day, I feel like everything is influence or sales, frankly. Now, that could be influencing my VP to adopt my new insights program, or it could be convincing my husband, John, to order sushi versus Italian on a Saturday night. Everything is influencing people. Everything is sales.

But that takes practice, Pete. I can’t just roll out of bed one morning and have that roll off my tongue. I have to narrow it down to my three, and then I have to practice, essentially, what is my elevator pitch, which works in so many areas of life – personal, professional, friendships, relationships.

Pete Mockaitis
And so, how are you defining superpower here?

Jenny Wood
So, I define it, basically, as your strengths, your passions, the things that you are particularly good at, because in all areas of life, everyone has a personal brand, whether they like it or not. It’s what people, essentially, say about you behind closed doors. We all have a personal brand. But how we want to control that narrative of the brand is ultimately up to us, should we choose to lean into that.

Pete Mockaitis
And it’s funny, when you said superpower, I was imagining super precise tidbits, such as identifying the hidden implications of a fact presented that others may overlook. So, for example, that’s a lot of words. Now, leadership feels pretty broad, what do you specifically mean by leadership?

Jenny Wood
So, leadership, first of all, is earned not granted. To me, a manager is kind of managing to spec. That’s actually something that Seth Godin says. Seth Godin and I had a conversation yesterday about his new book that just came out, great book, The Song of Significance: A New Manifesto for Teams. And leadership to me is a state of mind. It is an earned opportunity. It is having empathy for your team. It is ending each one-on-one with, “How can I support you this week?” It is the humble two, using the humble two if you’re in a group meeting.

And I refer to the humble two as these two statements, “I don’t know,” and “I was wrong.” If a leader can use those two statements in a big group of people that are reporting to them, that’s pretty powerful because, of course, we want our leaders to be right most of the time, of course, we want our leaders to have answers often, but for a leader to have the humility to say, “I don’t know and I was wrong,” and then thoughtfully follow-up, get the data that’s needed, get back to that team, that’s powerful stuff. And that, to me, is the difference that makes a leader.

Pete Mockaitis
I like that humble two notion a lot in terms of, “I was wrong.” Another variant of that that I really like is when you’re just in a group of folks chatting about potential ideas, possibilities. This is more about me than leadership as a whole, but when folks say, “I like your way better,” like they prefer what someone else said to what they, themselves, said. I just really love that because I think it speaks volumes.

I don’t know, it seems like there’s a good segment of the population. I think it feels like they need to be right and the smart one in the room. And those humble statements of “I was wrong, I like your way better” and anything in that whole family or cluster, I think, goes a long way to show, “It sure is not about my ego, but it’s about the thing that we’re trying to do here together.”

Jenny Wood
Absolutely. And the best thing you can do as a leader is to lift your people up, to lift as you climb, and to amplify their good ideas, because, as a leader, you get 100% of credit. And this could be a leader, this could be a principal of a school, this could be a leader of a union, this could be a leader in a big corporation, you get 100% credit for everything your team does.

So, that means if they fail, you fail. But if they succeed, you succeed. So, whenever I see a leader giving credit to their team, or sending the email to their manager, thanking their team and CC-ing their team below them for the great work they did, and giving credit, like that’s the leader I want to work for. That’s the leader I want to work for.

Pete Mockaitis
And when it comes to chasing things and doing the influencing, do you have any particular pro tips there?

Jenny Wood
Influence is so much about communication, and I know you’ve had a lot of guests that talk about communication. I know you have some listeners who are early to mid-career who are always looking to up-level their skills in all areas of life. So, one I like a lot is called delete the octopus. And if you’re willing to do a little roleplay here with me, I would ask you to…

Pete Mockaitis
This is where your improv experience coming to bear.

Jenny Wood
This is my improve experience.

Pete Mockaitis
I took one improv course at Second City for three days, so let’s see what I got.

Jenny Wood
Whoa, we’re now going to give you your Second City report card X number of years later. All right. So, let’s say, in this hypothetical scene we’re setting, that we are in a meeting together, and someone, and your manager says, “What are the biggest challenges on your team right now?” So, I’ll actually have you give that to me instead, and say, “Jenny, what are the biggest challenges on your team right now?” And I will offer two ways to answer this question because I think this is key to influencing effectively.

The first way will be ramble-y and not very buttoned-up, and the second way will be much tighter-structured and more buttoned-up. So, again, I’ll ask you to give me two opportunities to answer this question with you as my manager, and me as one of the people in this room of, let’s say, ten people. And the question is, “Jenny, what are the biggest challenges on your team right now?”

Pete Mockaitis
“Jenny, what are the biggest challenges on your team right now?”

Jenny Wood
“Oh, so many challenges. I mean, we started this new team that’s essentially a startup within our real estate industry here at our pretend company. And I really think that the priorities are kind of we’re just not set on our priorities yet, we’ve got a bunch of different goals, and we haven’t really figured out how we’re going to track our goals or what our metrics should be.”

“We also have so many confusing things around our tools and our technology, and things we’re doing in spreadsheets that we should maybe be outsourcing for different tools, which also reminds me that what makes this even harder is all the different regions that we have. We’ve got people in America, we’ve got people in Europe, we’ve got people in Asia. In fact, the other day, I was traveling to Asia and met with the team, but then I took some vacation days. I went scuba diving. I saw this really cool purple octopus on this night dive.”

“But I digress. Going back to the global challenges, blah, blah, blah, blah, blah.” All right. So, this tip is called delete the octopus, because I just gave a long ramble-y answer that made it really hard to influence you as my manager on what my biggest challenges are right now. So, now, I’m going to ask you to ask me that same question again, “Jenny, what are the biggest challenges on your team right now?” and I’ll answer in an upgraded way.

Pete Mockaitis
“Jenny, what are the biggest challenges on your team right now?”

Jenny Wood
“Our three biggest challenges right now are priorities, technology, and global alignment. Priorities because we’re a new team and we’re still figuring out what our goals and what our metrics are. Technology because we’re still doing things in offline spreadsheets that we should probably be using tools to solve instead. And, finally, global alignment because we have teams in America, in Europe, and in Asia, and if we were more coordinated, we could move faster and more efficiently. So, my three biggest challenges are priorities, technology, and global alignment.”

How much easier was that to understand?

Pete Mockaitis
Certainly, and especially in the context of management and influence that we’re talking about here. It’s, like, with the first, it’s sort of like, “Well, I don’t really know what to latch onto or what I might offer in terms of assistance in that world,” versus this, it’s like, “Oh, well, hey, we’re using this tool right now. It’s awesome. Does your team want access to it? Here it is.”

Jenny Wood
Exactly. Right. And this was all about influence, right? So, how do I influence you as my leader in any area of life. It could be a leader in a community center. It could be a leader in a social group. It could be a leader in any volunteer group. How do I influence you as my leader to help me with the things that I need to help me achieve my goals?

So, in this particular case, which is a professional example, my goal is to get more support from my manager on priorities, on technology, on global alignment. But if I give that long-winded ramble-y answer, there’s no way for you, as you said, to latch onto what I most need. And what is the specific tactic I used there?

The specific tactic I used was simply write down a list of seven to ten things that are problems, circle, let’s call it, two to three, and then when I start speaking, simply lead with those singular words. Just priorities, just technology, and just global alignment.

And that means that I also embrace the power of a pause, which people, early in their careers, sometimes think makes them seem less buttoned-up and not as smart or not as prepared, but it actually has a counterintuitive effect. It makes people seem smarter and more buttoned-up and more knowledgeable and prepared.

Pete Mockaitis
Absolutely. And on the receiving end of a pause, it’s funny, it just sort of galvanizes attention and builds a little bit of suspense. I remember my Uncle Topper, which was one of my first people I look to for speaking wisdom, episode 100, he would do that frequently in his speeches, and I was like, “Well, what’s he going to say next? Well, what is that?”

And so, it builds the suspense and gravity and attention all the more, which is great, which is what you want, people paying attention to you. As well as it actually saves time in terms of, “Ooh, I don’t know if I want to ‘waste’ the one minute of silence to gather it.” But, really, that one minute often will save ten minutes of ramble not gone down.

Jenny Wood
Yeah, exactly. And think of all the ways, areas in our life where you ramble – relationships, friendships. It’s also a way to show that you respect somebody else by slowing down and pausing and giving them a moment to speak, especially for those of us. Very hard for me early in my career, still hard for me on some days, I naturally speak to think. And I’ve had to retrain my brain, but it is retrainable, so that I can better think to speak, which is exactly what delete the octopus helps encourage.

Pete Mockaitis
Okay. So, when we’re chasing things, particularly in the career world, we got a clear understanding of your superpowers, and then some thoughts for how we communicate to be influential. Are there any other really top best practices/worst practices that you would highlight here?

Jenny Wood
Well, I would offer that a success mindset comes before success itself. And since I already talked impostor syndrome and all the inner gremlins we can have, let’s take a statement that we might say to ourselves that starts with “I” and has something negative after it. For example, “I don’t have my dream job yet,” “I haven’t met the partner I want to spend the rest of my life with,” “I don’t spend enough time with my daughter.”

So, I already kind of pre-leaked it in that first example by adding a very specific simple word, which is just the word yet. If you take any negative sentiment and you add the word yet to it, so let’s take the second to where I did not add it. So, the second one was, “I have not met the partner I want to spend the rest of my life with,” that’s an inner gremlin, then you add the word yet, “I have not met the partner I want to spend the rest of my life with yet.”
Or, let’s say I’m struggling with work-life balance, and I say, “I don’t spend enough time with my daughter.” Very negative, very down on myself. But if I add the word yet, “I don’t spend enough time with my daughter yet,” I have not yet figured out the right way to mix my professional and my home life in a way that serves me.

So, a success mindset comes before success itself, and adding that word yet can help with that growth mindset. Thank you, Carol Dweck and all your great work on growth mindset. It can help you overcome the negative speak, those barriers we put up in front of ourselves that prevent us from even starting something.

If I said on the subway that day, “Well, I haven’t met my partner, and it’s just all feudal,” well, that’s not the mindset you need to chase what you want. But if I sat there, saying to myself, “That guy is attractive. I am interested. I haven’t met him yet,” well, that’s the inspiration I need to get pushed out of my subway seat by some force that’s helping me chase what I want and achieve it.

Pete Mockaitis
Okay. So, inner gremlins, we add the yet. What else do you recommend?

Jenny Wood
I have a number of ways that I also like to encourage people to pump themselves up when they’re feeling like the work they produced that week is not as good as their peers, or the email they sent to their friend group was not as helpful as maybe they would want it to be, and that is this concept of “Meh.”

Not everything we do every week can be a ten out of ten, nor should it be because that’s bad prioritization. So, if you embrace the fact that some of the work you do every week, the emails you write, the texts you send to friends, the conversations you have with your partner, the slides you work on for your presentation, that some of them are going to be meh, then that helps you be a little bit more strategic with where you want to be above average and where you want to be below average because, by definition of how math works, 50% of everything you do this week will be below average.

Pete Mockaitis
Below your average.

Jenny Wood
Below your average, right. Exactly. So, if you look at the 800 or something podcasts episodes you’ve produced, 50% are below average of your average podcasts.

Pete Mockaitis
How dare you, Jenny?

Jenny Wood
How dare I? It’s radical. It’s radical. But it’s true because it’s just math, and being a data lover and an econ major in college, I can’t not share this because I think it’s so freeing. I think it is so freeing to recognize on those nights when you’re having trouble falling asleep because you feel like you didn’t nail the presentation, or those days that I didn’t pick up my daughter from school and I felt like a bad mom because I had a meeting that went too long.

On those days when we feel like we are not at our best, it’s actually quite freeing and helps us fall asleep at night to remember that you cannot be above average on every single task, every single day, every single week, every single year. And then when you do have that episode, and hopefully it’s not this one, Pete, but if it is, well, accept it because it’s just how math works. When you do have that episode that’s below average, you can simply shake it off, realize tomorrow is a new day, and say, “Not every single episode can be above average. Not every single episode can be in my top 10%.”

But some people really struggle with that and want everything to be the absolute best, the absolute superlative, but that gets in the way of trying things, taking risks, recording your next podcast episode, because if you were worried that every single podcast episode had to be the best you’d ever recorded, you probably wouldn’t do another one next week.

Pete Mockaitis
Absolutely. And that’s interesting when you talked about taking risks, this reminds me of folks who only took the easy classes they knew they would do well in, in high school or college. And, yep, that will probably get you a higher grade-point average when you’re all done. True. But it’s such a bummer in terms of the discoveries and the adventures and the expansion that could’ve been had you tried some things out that were different, uncomfortable, and probably below average.

Jenny Wood
I love that. Discoveries, adventures, expansions, that’s exactly what we want in life. And we think about taking risks, and in the book, I call this actually being a little bit reckless. I’ve got these edgy words I’m going to use to be a little bit exciting with the language and to encourage people that, sure, there are ways you don’t want to be reckless if it’s harming yourself or harming anybody else, but to be a little bit reckless and go with your gut.

Move to Australia for that semester abroad even though it seems scary and uncertain and it’s far away and you don’t know anybody. Be a little bit reckless in that kind of decision. Sure, dot the Is and cross your Ts on your mortgage forms and your tax documents, but in areas where you can take a little bit of risks, rather than doing considerable analysis paralysis, and weighing every single pro and con, go with your gut.

Be a little reckless, take a little risk because that’s when you do get the adventure, the expansion, and so many new opportunities you wouldn’t even know that you had coming had you just taken the easy class.

Pete Mockaitis
And that little snippet you shared about having trouble falling asleep because you had a bad presentation, I imagine you’ve worked with a lot of overachievers in your day.

Jenny Wood
I’ve worked with a few, one or two.

Pete Mockaitis
And in so doing, there is a theme that happens often in this population, that one can put their whole identity, self-worth, sense of value, into their performance, whether it’s work or family or whatever. And so, that notion, a person who does that may very well have trouble falling asleep when they made a bad presentation.

And that reframe associated with, mathematically, it’s just a fact that 50% of your work will be below your average, and to try and find peace with that meh is handy, do you have any other bits of wisdom for this population that struggles with that interior emotional challenge?

Jenny Wood
Well, this is not my wisdom but wisdom from social psychological principles. It’s called the spotlight effect. And it essentially means that, let’s say, for example, I do a lot of speaking engagements, and sometimes they’re really good, and sometimes it’s not my best day.

So, if I were losing sleep that night, thinking, “Oh, my gosh, I did this keynote for this organization, and I messed up slide seven.” And I’m, like, replaying it over and over in my head, and I’m anxious, and I’m tossing and turning, and the inner gremlins are roaring. I have to remember the spotlight effect, which is that I have a spotlight on me right now, focused on how I’d bombed slide seven, but any audience member is worried about the presentation they gave to their customer that day where they maybe messed up slide 11.

So, I’ve got a spotlight on me about slide seven in my presentation, they’ve got a spotlight on them about how they delivered slide 11 in their customer presentation, and, therefore, we could all just live happier, more fulfilled, more at peace if we recognized that people are never as worried about our mistakes, our transgressions, our slip ups as we are ourselves because of this social psychological concept called the spotlight effect.

Pete Mockaitis
All right. Good. Thank you. Well, Jenny, tell me, anything else you want to make sure to mention before we hear about some of your favorite things?

Jenny Wood
I’m so excited to talk about my favorite things. I think we covered it. It’s really all about asking for what you want unapologetically, and showing up each day in life and work and family and friendships unapologetically in a way that is about being bold.

Pete Mockaitis
Well, I guess I was just going to follow-up with…when it comes to asking unapologetically, when folks are in the heat of the moment, and they think they do want to talk to that gentleman on the subway, or to make that request, and they’re just scared, emotions, in the moment, what do you recommend they do?

Jenny Wood
Well, there’s a very practical thing you can do, which is simply breathe. Breathe in, breathe out, and to recognize, at least for me, I really struggle with uncertainty. That’s when my anxiety kicks in the most. Uncertainty about where to live, uncertainty about which house to buy, “Is it the right house to buy?” Uncertainty about, “Is this the right life partner?” Uncertainty about what to talk to my colleague about that might be a challenging conversation versus not.

To me, the anxiety lives in the uncertainty. So, if you contrast that with when you’re bold and ask for what you want unapologetically, or make a courageous move unapologetically, you tend to get an answer one way or the other. The answer might be yes. The answer might be no. But I, frankly, would rather live with a no and feel less anxious than live in the uncertainty and feel more anxious.

So, that always encourages me to get out of my subway seat and take the bold move, do the hard thing because I personally feel, and I hear this from a lot of people that I partner with as well, that uncertainty is very disconcerting to them and very stressful, and they’d rather have the answer, too, but people have a hard time taking that first step.

So, it’s almost like zooming out and seeing that long view of, “On the other side of this, I’d rather have the answer, even if the answer is no,” because, as Wayne Gretzky taught us in hockey, you miss 100% of the shots you don’t take, but if you take a couple shots, or get off the subway a couple times, you might end up with a husband, or a great career, or a great family life, or a great passion of a hobby.

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

Jenny Wood
Yes, I love this quote, “Rationalization is a weapon so powerful it should require a background check.”

Pete Mockaitis
Okay.

Jenny Wood
That’s by Dan Pink. Because we rationalize not sending that email to that prospective mentor, or not having the tough conversation with a peer who’s maybe a little bit more challenging to work with. It keeps us small and it thwarts our full potential when we rationalize why we shouldn’t take a bold move, or when we rationalize why we shouldn’t take a bold action or chase something we truly want.

Pete Mockaitis
Okay. And could you share a favorite study or experiment or bit of research?

Jenny Wood
Well, I do a lot on LinkedIn, and I offered a poll that, I guess, this is first-party research here, this is my own research, but I asked a poll, “Do you have a 10-year plan? Do you have a five-year plan?” And I think there’s this misconception with people earlier to mid-career that all the leaders they worked with had some big grand 10-year plan or five-year plan, but the data actually is counterintuitive and suggests otherwise.

Eighty-one percent of people, that’s almost 2,000 people who answered, did not have a 10-year plan. I think it was about 56% of people did not even have a five-year plan. So, that’s why everything I’ve spoken about in this conversation so far has been to help you, listeners, do big small things – that’s actually the name of my newsletter, Big Small Things – to cast votes for the future person you want to be, to cast votes for the goals that you want to achieve because it’s not some big colossal 10-year plan. It’s really about the big small things you do every day to move one step closer to your goals that you’re chasing.

Pete Mockaitis
Okay. And a favorite book?

Jenny Wood
Build for Tomorrow by Jason Feiffer. He’s been a guest on the show, and he is just so wise and so smart. His four phases are panic, adaptation, new normal, and wouldn’t go back, which is a bit counterintuitive, that last one. Episode 848 on your show.

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

Jenny Wood
I like the four Ds. When you’re looking at your to-do list, the four Ds are do, delay, drop, and delegate because that really helps you structure. If you have 20 things on your to-do list, you don’t have to do them all today, you don’t have to do them all this morning. And my favorite one is delay because sometimes when you delay, something just falls off the to-do list because either it’s decided it doesn’t need to be done, or somebody else takes care of it, and then, poof, it goes away.

So, if you just write down delay next to a couple tasks, you feel like you’re in control of your to-do list, but you don’t have that feeling of overwhelm to get through every single item. So, the four Ds are do, delay, drop, and delegate.

Pete Mockaitis
All right. And a favorite habit?

Jenny Wood
A favorite habit is using a checklist each day. So, I’m a pilot for fun, a private pilot, and the other day I was taking my kids up to fly, and my five-year-old daughter said…I was going through my checklist so I said, “Mixture reached. Avionics on. Flaps up,” as I went through the takeoff checklist. And she said, “Mommy, what are you talking about?” And I said, “I’m going through the checklist. This is to have a safe and effective flight.”

And I like to bring that concept to my day-to-day as well. So, rather than wake up in the morning, immediately check my work email, and start reactively responding, I have a checklist. Exercise for 30 minutes. Meditate for five minutes. Spend 60 minutes on the project that is most important but probably the one I’m going to procrastinate when my inbox takes over. So, by having that checklist – exercise, meditate, 60 minutes on the key project – that helps me set up my day, like a good pilot of my day, for a, I guess you could call it, safe and effective day, or productive and effective day.

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

Jenny Wood
“Serendipity isn’t found; it’s made.” And I made my own serendipity on the subway that day. The New York Times wrote about this story, and the title of the article was, “Serendipity one, spreadsheet zero” because I mentioned I do everything in spreadsheets. I even had the spreadsheet of all the people I was dating, I’m super organized, and kept track of it all.

And so, on that particular day, serendipity won out, but I made the serendipity. Luck is when preparation meets opportunity, we all know. So, that day, I made my own serendipity by making the bold move to chase what I wanted unapologetically.

Pete Mockaitis
Okay. Well, now I want to know, in the spreadsheet, one of the columns is the name.

Jenny Wood
Uh-oh, here we go. Here we go.

Pete Mockaitis
What are some of the other columns in that spreadsheet?

Jenny Wood
So, it wasn’t so much an evaluative spreadsheet. It was a spreadsheet so that I was prepared walking into date. So, it would be name, and this was like a lot of early days online dating, so it was mostly about anything we’d talked about online. It was probably logistics, too, where we were going, what time, whether we’d spoken on the phone, and then kind of key nuggets about what we’ve talked about so I walked in somewhat informed when I went into that conversation.

Pete Mockaitis
Well, yeah, and if you have a lot of online dating people, you might just straight up get mixed up, like, “Whoops, sorry about that. That was the other guy.”

Jenny Wood
Yeah, I was trying to be a good partner.

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

Jenny Wood
I post on LinkedIn almost every day, but I mentioned my newsletter, Big Small Things, which you can sign up for. It’s a super short nugget that you get, delivered right to your inbox, lots of things like we’ve talked about that are highly actionable to help you be successful and chase your goals. And that is at ItsJennyWood.com/newsletter. So, I-T-S-J-E-N-N-Y-W-O-O-D.com/newsletter.

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

Jenny Wood
Well, I think it’s just asking for what you want unapologetically. So, as I mentioned, it’s easy to not do it because it’s easy to not ask for something. Rationalization is a weapon so powerful it should require a background check. It’s easy to rationalize not asking for something, not sending back the lukewarm mashed potatoes at a restaurant because you rationalize that you don’t want to bother the server, or rationalizing not saying to your colleague, “Hey, I’d really love to take the lead on our client presentation next time because I want to grow that skill,” because, “Oh, I feel bad and it’s not really my place to the lead. That’s their responsibility.”

But the people you work with are not mind readers, the server at the restaurant is not a mind reader that the mashed potatoes are lukewarm, your manager is not a mind reader that you want to challenge yourself in a new way, so you have to have the confidence, that swagger, that agency to ask for what you want so that you can get what you want.

Because in any room that you’re in, nobody cares more about your goals than you do. So, it really is up to each of us to have that agency, to have that confidence, to find that swagger to go after what we want because there’s nothing wrong with having goals and chasing them.

Pete Mockaitis
All right. Thank you. Jenny, I wish you lots of luck with all your chases.

Jenny Wood
Well, thank you so much. You, too, Pete.