Creating Confidence with Heather Monahan - Confidence Classic: The 4 Phases of Change That Shape Your Next Level with Jason Feifer
Episode Date: January 6, 2026Change doesn’t knock politely. It shows up fast, disrupts your identity, and forces you to question what’s next even when you thought you’d finally “made it.” In this episode, I sit down wit...h Jason Feifer, Editor-in-Chief of Entrepreneur Magazine to break down why change feels so destabilizing and how to move through it without panic, paralysis, or clinging to the past. Jason shares the 4 phases everyone experiences during change, why panic is normal (even for high performers), and how to reframe disruption as opportunity instead of loss. Get ready to stop fearing change and start building for tomorrow. In This Episode You Will Learn Why PANIC is the first (and normal) response to change. The 4 phases of CHANGE and how to move through them faster. How to reframe CHANGE as gain instead of loss. Questions that help you regain CONTROL during uncertainty. How to separate your IDENTITY from your title, role, or output. How to define WHO you are in a way that can’t be taken away. How to reframe failure as DATA instead of a dead end. Check Out Our Sponsors: Shopify - Sign up for a one-dollar-per-month trial period at shopify.com/monahan Quince - Step into the holiday season with layers made to feel good and last from Quince. Go to quince.com/confidence Timeline - Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Northwest Registered Agent - protect your privacy, build your brand and get your complete business identity in just 10 clicks and 10 minutes! Visit https://www.northwestregisteredagent.com/confidencefree Resources + Links Get your copy of Jason’s book Build for Tomorrow HERE Learn more about Jason Feifer HERE Call my digital clone at 201-897-2553! Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/ Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Jason on Instagram & LinkedIn
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We are in a state of constant evolution.
We should live in permanent beta,
which is to say to think of ourselves as a product in beta
that never is finalized,
is always being refined and revised.
And if we think of it that way,
when the change comes to us,
even if it comes to this thing
that we feel like we've reached our
wouldn't go back moment,
we've redefined ourselves,
we got there,
and now change is coming again.
We have to just see that
as another part of the natural cycle of things
and an opportunity to build even more.
Come on this journey with me.
Each week, when you join me,
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Hi, and welcome back.
I'm so excited for you to meet my guest this week.
He's been on the show once before, but we're glad to have Jason Fiper back.
He's the editor-in-chief of Entrepreneur Magazine, a startup advisor,
host of the podcast Build for Tomorrow and problem solvers and has taught his techniques for adapting
to change at companies including Pfizer, Microsoft, Chipotle, Draftings, and Wix.
He has worked as an editor at Fast Company, Men's Health, Boston Magazine, and's written about
business and technology for the Washington Post, Slate, Popular Mechanics, and others. Jason,
thank you so much for being back with us today.
I am honored to be back. Great to see you.
Great to see you, too. So we were just offline talking about the fact that.
that both of us are going through moves right now
to get out from small, small time living,
two-bedroom type apartments
and get into bigger, spacious opportunities.
And I know that you just wrote a book
about change and adapting change.
And it's just so funny that right now,
you and I are like all in embracing change in this moment.
I know.
Well, I am excited for your move.
I'm excited for my move.
I'm excited for everybody's move.
So this book, Build for Tomorrow.
It's funny, we were talking about,
where we live and we're going to move because I wrote this book during this major disruption in
my life. So when the pandemic began, literally the day that schools closed down in New York City,
which is where I live, my wife and I, we have two little boys. We live in the right now at
1,000 square foot, two bedroom apartment. And we were like, we don't know how long we're going to
be locked in here, but it's going to get crazy with these two little kids. So my parents live in
Boulder, Colorado, and they have a house and outdoor space. And we thought that's just going to be
a much better environment for our kids. So we went out there for what we thought would be,
you know, who knows, but it turned out to be 18 months, which is crazy. I know. And the reason was
because schools, because camps opened up out, the summer camp opened up out there. It hadn't opened up
in New York. And then we got them into a school that was going to be open the whole year, whereas it
was kind of iffy in New York. So anyway, we stayed for 18 months. And I kind of tell you,
I went through this process when I was out there, which I then recognized in so many other people,
which was I spent quite a while, once we knew we were going to be there for a while,
I spent quite a while defining myself against this new area.
I was like, I'm a New Yorker and all this, all this Boulder stuff.
I don't like, everybody here just wants to talk about like hiking and these are not my people, right?
You know, this is what we do.
The very first thing that we do when change comes to us is we panic and we try to
to hold on to what we had before because we experience the change as a loss. And I was feeling
a loss for my identity as a New Yorker because here I was in Boulder. And what I came to realize
after 18 months there was, oh, actually, it's kind of wonderful to step away from work and go
on a hike in the middle of the day. I'd never done that before. I never even thought of that.
And that doesn't mean that I lose my identity or the things that I kind of orient myself around,
but rather that I can add things and I could discover new things.
And I came out of that experience with great new friends and some new lifestyle habits,
frankly, and a sense that I had reached what I now like to call wouldn't go back,
the final phase of change where I say, I have something so new and valuable.
I wouldn't want to go back to a time before I had it.
I mean, we came back to New York, but something in me had changed.
I wanted something different.
I wanted a somewhat different pace of life.
And that drove us, for example, to my wife and I to find a,
house in Brooklyn that's further out. It's not in the center of the action like we're in now.
We can't just walk around the corner and have amazing restaurants anymore. But we have this
space and it's going to afford a different kind of pace and lifestyle. And I got that out of this
change that I didn't know I needed, but I did. Wow, that is shocking. I completely understand
when you're talking, I'm thinking in my mind, the analogy for me is when I got fired. And when it first
happened, you know, just sheer panic. What is going to happen?
and the unknown, the uncertainty is so scary.
How do I fast forward through this window of time
and get to something stable?
And like you said,
and then inevitably reaching a place
through your four-step process
where you are finally in a moment saying,
oh, I don't want to go back again.
I'm so glad this all happened.
I embrace this new thing.
But those middle steps in that beginning
are definitely challenging.
Can you break down those four steps for everybody?
Yeah.
So I gave you the bookends of it.
So this is something I realized during the pandemic.
I was going into it.
For years, I've been studying how entrepreneurs are adaptable
because I found that adaptation is really the key driver for success.
But my question was, how are they doing it?
Because it doesn't seem to be something people are born with.
It seems to be something that they are learning.
And then the pandemic happened, and I got to watch, we all got to watch.
Everybody go through the same change at the same time,
but some people seem to move through it faster
and some people move through it slower
and some people tried to hold on to what came before.
And I realized that everybody goes through change in four phases.
They are panic, adaptation, new normal, and wouldn't go back.
And it's really, it's illuminating to watch people go through this
at different paces because what you get to realize
is that everything that you experience is totally normal.
even if you are deeply successful, even if you have a lot of advantages that other people don't,
you will still panic at the very beginning of chance.
You will.
And then you will be forced to figure out how to adapt.
What are the things that are available to you?
Then you will develop a new normal.
You'll start to have a foundation that you can build upon and you'll discover some new
familiarities.
And eventually you will reinvent the thing that you're doing or the way that you think about
yourself.
And you will get to that point that wouldn't go back moment, which is available for
us all. And I think that the greatest challenge is not moving through these phases because we
will all move through them, but rather how fast can we move through them? How efficiently can we move
through them? How thoughtfully can we move through them? Because that's how we get to new opportunity
and growth. Well, sometimes before anyone else does. How do you get through the panic phase
faster? Because for me, I hate that phase. That is like, oh, it's my worst nightmare. I can't
stand it. Right. Me too. It's awful. Feeling that panic is terrible. And there are a number of things
that we can do. First of all, I think we need to recognize what we're actually doing in our heads,
which I alluded to a little bit earlier, but just to dive a little deeper into it. What we are doing
is we are equating change with loss. So when change comes to us, the very first thing that we do
is that we identify the thing that we're going to lose as a result.
I'm no longer going to have access to this.
I'm no longer going to be able to do this comfortable thing.
I used to do things in a certain way and maybe now I'm going to have to change it
and that feels like loss.
And then because what we want most of all is to be able to know what's coming next.
We all want to know the future for ourselves.
We start to extrapolate based on the information that we have.
And if what we're seeing is loss, we're going to extrapolate the loss.
So we're going to say, well, because I'm losing this, I'm going to lose that.
And then because I lost that, I'll lose this other thing.
And then very quickly, we start to feel like we have absolutely nothing under our feet anymore.
And so one of the things we need to do is just simply reframe the experience as one in which we are trying to find gain.
Gain is harder to see because you don't see it immediately.
That story that I told you about moving to Boulder,
one of the great gains that came out of that
was that I started to be more mindful
of what I needed outside of work
and thinking more about my physical health
and taking time for myself.
I didn't know that I needed that.
That was gain that came later.
For a long time, I was just focused on loss.
So how do we do it?
Well, I found that three simple questions
can help start to get us there.
And those questions are, number one,
what is the new thing that we're doing?
Right? Just like, let's just lay it out. Number two, what new habit or skill are we learning as a result?
And then number three, how can that be put to good use? Because once you limit the way in which you're
evaluating something based on how can this be put to good use, you're forcing yourself to at least have some
kind of answer there. And it may not be the right answer. You may not know exactly, but what you're
going to start to do is explore and experiment with your hypotheses. Well, how can this be put to good use?
I don't know. I guess if I live in this different city than I did before, one of the things
that I'm learning is how to live somewhere else. I didn't know that I wanted to live somewhere
else. How can that be put to good use? Well, I guess if I realize that I can make it work somewhere
else, that tells me that I don't maybe need to hold on to everything that I'm comfortable
and familiar with and I can start to open myself up to the possibility that I'm more adaptable than
I thought I was and maybe new opportunities that I had discounted or ones that I should consider
now. You see how you can start to push yourself to reframe things as change as gain. And that really
starts to push down that panic. Heather, I don't know how you're going to produce this afterwards,
but what just happened in case we cut it out is that my seven-year-old just came into the room
and demanded that I get up and get him something out of the fridge that he can very clearly
get himself. And then he decided to put my Oculus 2 on, even though it wasn't on. And then
He said he couldn't see, and it was a whole thing.
And then finally he left.
You said, thank goodness for editors, which is true.
Thank goodness for editors.
But also, I realized this interesting thing during the earlier days of the pandemic
when my kids were home all the time, as, you know, yeah, as you know very well,
I saw a major eye roll there, which was that they would come and they would like burst in
on me doing things that were live.
There was no editing.
Sometimes I was giving a keynote talk that people were paying me to do, right?
And they would come burst in and they start climbing all over me.
I was doing like live webinars for entrepreneur and the kids would come bursting in.
And at first, my instinct was to just get them away as fast as possible or ignore them or something.
But then I came to realize that for the audience, the kids interrupting was a highlight because it was relatable and because they have gone through that themselves and because it showed this humanness of experience that's far.
different from my professional presentation, and they really liked it. And I came to realize that sometimes
the things that we think are dragging us down can actually be great assets. And so now, if we were doing
this live, if you and I were doing this live, I would have played that differently. Like when my
kid came in, I engaged him, but I was basically like, how can you leave this room, right? But if we were
doing it live, what I would have done is I would have just grabbed him, plopped him in my lap, and kept
going. And he would have said something funny, and I would have made a joke about it. And everyone would
have loved it. And afterwards, people would have told me that that was the thing that they
remember. So sometimes we can't always be so afraid that something is going to go wrong,
because sometimes the thing that goes wrong can be turned into the thing that is most memorable
in the good way.
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I ask you to try to find your passion.
Oh my gosh. I love that.
And thank you for sharing it.
This is so good.
And in my mind, this is what popped into my mind.
Right before the pandemic hit,
I was interviewing Sarah Blakely live in Boston
for a hypergrowth conference for drift sales and marketing event.
And when I was walking out in front of her to introduce her
and my feet get really, really sweaty when I'm nervous.
And of course, I always have four-inch heels on.
And so I'm walking out my Christian loupotons in front of thousands of people
with Sarah Blakely right behind me and my foot comes out of my shoe.
and I almost face-plan on the stage in front of everyone.
I was able to catch myself.
And so I jumped up and said,
major shout out for the hometown girl who didn't face plan.
And everyone went wild, Jason.
Like, it was, they thought it was so funny, right?
I just had a joke about it.
And then Sarah started laughing, then we high-fived.
And, like, the next thing you knew,
everybody was with us.
And after the event, people were like,
wow, that was so funny that you made a joke about,
falling. I'm like, who knew
that was going to be the thing that got people fired up?
I know, because that's the human
thing, right? Because the people
in the audience are not
in a position to be getting on
stage and interviewing Sarah Blakely,
but they definitely have fallen
in their shoes, right? And so
when they see you do it, they feel that
instant connection. This is what we
should want. We should want to
break down boundaries. And we should
also be open to
that sometimes the greatest things are
going to happen to us are the ones that we didn't plan for. As you were telling that story,
which I love, I was thinking about, I was in Maine last week, and there's this, in Oxford,
Maine, which is this tiny little town. There's a, there's like a country store, like a farm stand
or whatever, called Smedbergs. And Smedbergs has a giant sign in front of it, advertising that
they sell Lobster, L-O-B-E-S-T-E-R. Now, what is going on with that? So I went inside and I
because I was like, that's not how you spell lobster.
And surely somebody has told them that, right?
And so the story is that years and years ago,
the owner was making a sign to advertise their lobster,
and she had done it, L-O-B-S-T-E-R.
And one of her employees was like,
oh, no, no, no, you're missing an E.
It's L-O-B-E-S-T-E-R.
And so the owner who was like, oh, well, I guess she knows,
made a sign that said, lobster,
and then put it out front.
And people thought it was hilarious.
And they, you know, they very quickly realized
that it was a misspelling. But it distinguished them. Suddenly, Smedbergs became the lobster place.
And people started to remember it as the lobster place, which, you know, in a region where
everybody's selling lobster, I mean, a lobster is a lobster. It's hard to differentiate.
And so they've kept that thing up for years now. And they even sell shirts that say home of the
lobster. And they really leaned into it. And people love it. People love Smedberg. And, you know,
you could have been embarrassed by that. And you could have taken the sign down in media.
but by owning it and having fun with it and just being able to break down that barrier a little bit between you and the people that you serve, you can really just create so much.
That's so funny. And I love that they developed a product line with T-shirts out of it. I mean, it's like a great unique value proposition. They've separated themselves from everybody else out there doing the same thing and made themselves memorable. So that is an excellent story. I love it. Okay. So we've talked about the four phases. What's the most important phase in your opinion?
Well, it's a good question.
You can't have one without the other.
You're going to go through them all.
I think that the most important phase is also the most challenging one.
And that is the obvious way to answer that is wouldn't go back is the most important because
it's the goal of the whole thing.
What you want to do is get to this moment where you say, I have something so new and valuable
that I wouldn't want to go back to a time before I had it.
That's the goal.
But I'll tell you, it's also the most challenging because once we get to wouldn't go back,
we're going to want to hold on to that for dear life, right?
We're going to have this new thing.
It was hard to get to.
You know, think about it for yourself, right?
I mean, you reinvented your career and now you've got what you have now, and it's amazing.
But it's not going to be like this for the next 70 years, right?
Some other kind of change is going to come to it.
And when that happens, all of us were going to say, oh, no, but I went through this whole process.
And it was so hard to get here.
And I don't want to give it up now, right?
And what we have to remember is that we are in a state of constant evolution.
We should live in what Reid Hoffman, the co-founder of LinkedIn,
likes to call permanent beta, which is to say to think of ourselves as a product in beta
that never is finalized, is always being refined and revised.
And if we think of it that way, well, then when the change comes to us,
even if it comes to this thing that we feel like we've reached our wouldn't go back moment,
we've redefined ourselves. We overcome obstacles. There was a lot of struggle and challenge and we got
there and now change is coming again. We have to just see that as another part of the natural cycle of
things and an opportunity to build even more. I think again, we cannot go to this place where we think
that the only things that we will ever have are the things we already have. We need to instead be able
to set ourselves up to think that when change comes, it's an opportunity to upgrade. Now, one of the ways
that we can do that.
It is a really important mental exercise.
I think we shall go through.
Everybody should go through this.
I should be curious if you have
and what your answer is,
is to very clearly separate
what we do and why we do it.
And the reason for this is because
I think that we too often identify
with the product of our work,
with the output of our work.
We think of ourselves as, what are you, what do you do?
Well, what I do is I produce this thing.
And that's fine,
identify too closely with that. If that's your identity, then as soon as that changes and it will change,
you are going to feel completely unmoored. I mean, Heather, if you thought of yourself only as a
podcaster and then tomorrow the podcast industry falls apart, right, well, you're going to feel
completely unmoored. You're going to feel like, well, now I'm nothing. But if you can identify something
about yourself that is so core, the value that you provide to people is,
so intrinsic to you that it can survive any change. It is the thing that does not change
even in times of change. Well, then you have an orientation point whenever there's a moment
of disruption. So for example, for me, I have the sentence that I tell myself, I tell stories
in my own voice, right? It's very different from, say, I am a magazine editor. Because I'm a
magazine editor is contingent upon me having a job in magazines. Easy to not happen. But I tell
stories in my own voice. Well, stories is anything. Stories is newspapers and magazines and
podcasts and speaking on stage and books and whatever. And in my own voice, I'm setting the
terms for how I'm going to operate. This is the work that I will do. Now, anything can change.
Anything can come at me. After this conversation, I could check my email and entrepreneur could say,
Jason, it's been a good run. We're sick and tired of your face and goodbye, right? And I hope that
doesn't happen. I'm not interested in that happening. But if it does happen, it doesn't impact my
ability to tell stories of my own voice. I have an orientation point. We all need that. Have you thought
through something like that for yourself? No, I haven't, but it's really, really helpful. And I think,
like you said, it's going to help everybody listening right now because what I just walked through in my
mind was when I got fired, I felt like I'd lost everything because I lost my chief revenue officer
title, right? I was thinking of what's intrinsic to me that I can bring with me wherever I go. I
wasn't thinking that way. I was thinking this has been taken from me and I had a non-compete. I had to
leave and abandon what I was an expert in. That's when the panic set in. Step one, panic came in hard,
right? But then I also thought to myself, to your point with the pandemic, I went through a much
smaller version of that, but I had really stepped into my speaking business had taken off a year
before the pandemic came. So I was really identifying with myself as a speaker. That's who now I
have become in my mind. But same thing, you know, using that same methodology, it doesn't need
to be a title of speaker or title of chief revenue officer or title of editor. It's who are we
intrinsically so that we don't, that can never be taken from us. And I've never actually sat down
to do that exercise. So thank you so much for sharing that. That's really powerful. I give that advice
when I speak to companies a lot because people bring me in to help their teams navigate moments of
big change. Sometimes it's in their industry. Sometimes they've gone through a reorg.
And I ask people to answer that for themselves.
And the answers are really interesting because to give a sentence to yourself,
to give a kind of mission that isn't subject to change is to drill down really,
really deep.
And so people will often, they'll say things like, I am a problem solver, right?
Or I am a builder.
Or I help people achieve their own greatness or things like that, right?
And, you know, if you spend a little more time with it,
you can maybe get a little more eloquent,
but I think those are really wonderful starting points
because that's something that's transferable.
It's really interesting when you got fired from that job,
of course, the very first thing so natural that you thought of
was, okay, I don't have access to that title anymore
and I don't have access to being able to do exactly
the kind of work that I was doing in the arena that I was doing it.
And so that felt like a total loss.
But the reason why you have been able to build everything that you've built
is because there were these deeper transferable skills inside of you
that you weren't immediately recognizing, but that were there.
And then you started to apply them in other areas and other arenas.
It turns out that you had a whole body of knowledge that you could build upon
and that you could use in completely different ways.
And you didn't see that at first because you were so laser-focused in
on identifying with the product of your work rather than going deep enough
and seeing what are the things that are transferable.
And when I talk to people who have gone through these kinds of changes,
I often hear a moment like this where they lost access to whatever it was they had before.
And then they spent some time figuring out, like, what do they have?
What do they have?
And it turns out that what they have is pretty powerful.
Stacey London comes to mind.
For example, Stacey London, a name people might recognize.
She was the co-host of What Not to Wear on TLC for a long time.
So Stacey's become a friend.
And after a great run in television, she basically, you know, I mean,
This is how she would say it.
So she based, she kind of aged out of it.
Like she, you know, like the television networks just weren't as interested in her.
And she was feeling that and she was struggling with it.
She was getting older.
And she had this opportunity to take over a company called State of Metapause,
a company that makes products that help women with symptoms of menopause.
And at first, Stacey said, well, this isn't me.
I don't know how to do this.
I, you know, I've been in television my whole career.
And then she realized, no, no, no.
I'm a truth talker.
That's actually what's at my core.
That's what drove my success in television.
And that's what would drive my success here
because I'm going to engage in difficult subjects.
That's what I did in television.
And now I'm going to engage people in difficult subjects
with this company.
And once you recognize that deep, deep thing inside of you,
it really liberates you to find other opportunities
that you know you can master.
That's so good.
And yes, I definitely have followed her
and I think she's an amazing person.
And I love that she was able to make that change.
This is what just quapped in my mind.
It's not who you think you are.
It's who you think you are not, right?
And it's that idea that you're saying, okay, is that possible for me?
Well, that definitely isn't possible for me.
You know, we put ourselves in these boxes.
And I remember for me having that one day, I don't remember.
It was right after I met Elvis Duran and he said to me, you're writing a book.
You know, I allowed him to speak a truth into me.
And I said, okay, if he believes that, that could, it's possible maybe because he thinks
and I had him on a pedestal, and I'll tell you, I saw it with that for a while, like,
could I really be an author?
You know, does someone need to give me permission?
You go through all of these conversations with yourself when at the end of the day, I finally
made a decision months into this.
You know what?
I'm blowing up the lanes in my life, and I'm going to live my life lanelessly with my talents
wherever I go.
And I'm sure I'm going to fail at some of them.
I failed miserably with Perry Ellis and a clothing line that we launched and that did not take
off.
But then my book did incredibly well.
My podcast did, right?
There were these other things that did well,
but it was all the key was just to keep moving forward
and instead of getting caught up, hung up, and stuff on what we are not.
So I really love that.
I love that way of thinking about it.
I will add another way of framing that exact idea,
which came to me via Malcolm Gladwell.
So I was interviewing Malcolm Gladwell for the magazine a number of years ago.
And I asked him this question that was,
a little selfish because I, you know, I was curious as a person in media myself.
I wanted to know how Malcolm, who is a, for people who don't know, bestselling author
and top podcaster and every huge, just it's hard to compare.
And, you know, everything that Malcolm does is so distinctively Malcolm Gladwell, right?
Like, there's just an essence to the things that he does.
And I wondered how he has a filter for what is a Malcolm Gladwell project.
How does he look at something and say, this is a Malcolm Gladwell project?
or this isn't. So I asked him that, and he said, you know, to the best of his ability,
it's not 100% possible to do this, of course, but to the best of his ability, he tries not
to define himself at all because he said, and these were the words, as soon as he said these words,
I jotted them down and I slapped them on the wall, because self-perceptions are powerfully
limiting. And, yeah, it's a great line. Self-perceptions are powerfully limiting. Because if you have
a very specific idea of who you are and what you do,
you will turn down everything that does not match that.
But as it turns out,
some of the greatest things that we will do
were the ones that fall outside of some narrow conception of us.
Malcolm gave the example of podcasting.
You know, he had been a New Yorker writer and a book author,
and the idea of a podcast first didn't make sense to him.
You know, why would I do that?
you know, I'm a written word kind of guy.
And after enough conversations, he decided, no, why don't I give it a shot?
And now, of course, it's a core part of his brand.
It's great.
He has a show.
It's called Revisionist History.
It's fantastic.
And I really try to digest that.
It's hard because we all want to feel like we have a good sense of ourselves, and we should.
But we should also be pushing back against that and asking ourselves, well, what else can we do?
or what am I missing here?
Where are the opportunities that I could thrive in
that I haven't even given myself a chance to explore?
So I'll say it again, self-perceptions are powerfully limiting.
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One thing that I was just thinking of in regards to your framework and the exercises in the book,
did you think of applying this?
We're talking about everything from a business context.
Did you think of applying this to relationships as well?
Oh, yeah. I think that a lot of this stuff actually can apply really well to basically any part of your life. I'll give you a funny story, a funny embarrassing story.
So one, I believe that we should treat failure like data, which sounds like a very businessy thing. But when we try something and it doesn't work out, instead of thinking this was a terrible failure, we instead say, this taught me something. In fact, it taught me something that I now know better than other people. And that's a powerful insight that can be used in lots of ways.
Dell, when I interviewed him of Dell, told me that he keeps, he keeps mementos from the company's
failures in his office, not as a reminder of what went wrong, but rather as a reminder that sometimes
when things go wrong, they teach you, they teach you what you need to know to build something
correct the next time. And so I really have always tried to say, what can I learn from this
thing that just happened? And now I will tell you the embarrassing story. So when I moved to New York,
I moved to New York.
I was 28 years old.
I was living in Boston previously,
and I had just broken up with my girlfriend of,
don't fall on the floor when I say it, of nine years.
We started dating sophomore year of college,
and we were together until I decided to move to New York,
and that broke us up.
Obviously, it was not the right relationship
or we would have, you know, advanced that thing along.
But anyway, point is that I moved to New York.
I was single.
I had never been on a date before.
Never.
And because, you know, I started dating,
this girl was a sophomore year of college.
So I'm excited.
I go on to OKCupid
and like, you know,
immediately start chatting with,
and I should just dissituate.
This is 2008.
So this is like pre-Tinder
and in fact,
pre-dating apps.
So like I'm on desktop here.
And I'm on OKCupid
and I meet this girl who in my memory,
I think her name was Talia.
I could have forgotten her name at this point.
But anyway,
so Talia and I kind of hit it off
and we decide.
let's go out. And so, you know, again, I don't know anything about dating. So I suggest, why don't we go get dinner this Friday, which later I would find, that's not a good plan for a first date, but because there's too much commitment, right? So anyway, we meet for dinner. We meet under this bridge. We meet under the Queensborough Bridge. And then we walk to dinner, which is a few blocks away. And we sit and we have a great conversation and goes really well. Afterwards, she's like, yeah, you want to walk around? It's great. So we walk around the city for like an hour or something.
and we end up back under the Queensborough Bridge, where we had met.
And we're talking for a moment, and then, you know, conversation seems to kind of wind down.
And she's looking expectantly at me, or I think she is.
And I don't know what she is expecting because I've never, ever done this before.
And so I think to myself, what am I supposed to do?
Like, what does a 20-something do in this moment?
Before I tell you what I did do, what do you think I should have done?
I don't know. I mean, is she wanting you to kiss her? Or was she saying, why haven't you taken her dinner? It had to be one of the two.
So I was thinking, all right, yes. I mean, that was definitely one of the options, right? Like, does she want me to kid? Like, what is, what's happening? It seems like this part of the evening has concluded, what is the next thing? So the next thing must either be a, hey, it was really great to meet you and a hug. Or be, it's me going in for a kiss. Or it's C, me like inviting her back to my place.
because we're in our 20s and, you know, that's a thing people do, but I don't know. I don't know.
And so I just, I figure, you know, let's go big. I'm going for option C. And so I invite her back.
And her entire demeanor changes. She's like, suddenly, she's like, does that what you expected to happen tonight?
And I was like, I don't know. I'm sorry. And she's like, she's like, I didn't expect that.
And I was like, I'm sorry. I just, you know, I just got out of relationship. I just, I don't know dating very well.
she just got out of a relationship.
How long was it?
And I was like, it was nine years.
She's like, nine years.
Now I went into the end.
And I was like, last week.
It's just like last week.
And so, you know, now she's like, eurious at me, right?
Urius that like, here I am.
I just got out of this long relationship.
I'm like, I'm wasting her time.
I'm asking her back to my apartment, which apparently was very offensive.
And I am in a panic here, right?
So uncomfortable.
But I was like, okay, well, I know what to do.
Right.
Like the thing to do is just apologize.
Wrap it up.
All right. And so I eventually I was just like, look, I'm really sorry. I misread the situation.
It was really nice to meet you. And I think I might have offered a handshake or something. And then that was it. And then I walked away.
And ran away. Ran away. And afterwards, afterwards, as I was walking home, I got to tell you, I didn't feel, I remember this so clearly. I didn't feel bad. Instead, I felt like I know more.
now than I did before.
Like, I hadn't been on a first date yet.
And now I have.
And I learned some things.
And, you know, Talia, the stakes were really low here.
I wasn't supposed to meet and marry Talia.
I was supposed to have a first date and see what that's like.
And I did it.
And it went okay for a while and then it really went south.
And that's okay, right?
Nobody got hurt.
And I learned something.
And now I feel emboldened.
did that the next time I go out, I just, I know more than I did before. That's the healthy way
to be. It's funny, I was recently talking to Annie Duke, the former professional poker player
and decision-making expert. She wrote a couple best-selling books. And she just wrote this book
called Quit about why quitting is a, is an overlooked and important strategy. She said,
look, you know, you got to think about everything like dating in a way, which is to say, if you had to
marry the first person that you went on a date with,
you'd be afraid to ever go on a date.
You wouldn't.
Or it would be such an insanely challenging process
to go out on that date.
But the reason why we do go on dates
is because we can try something
and if it doesn't work, we can move on to something else, right?
We can meet somebody and if it's not compatible,
we just go meet somebody else.
And we need to think about everything that way.
We date ideas, right?
We date directions.
We date experiences.
And sometimes they're going to be really good.
And sometimes they're not.
And that's okay because not everything is supposed to be a full-time forever commitment.
Something is we just try things.
And so that's how I see a lot of this stuff about managing change as being applicable outside
of work because I think that ultimately what we really need to do is take this mindset of
we are adaptable.
we can learn, we can grow, we should be pushing ourselves to expand who we are
and what we do. And that has to happen in every part of our lives.
This is so good. And I love the dating story, but I also like how you just wrapped it up there
with the author of quitting. I really like that came full circle and it's super, super helpful
because we all need to apply that methodology and that reasoning in our life. And even
I'm just saying here thinking my own life right now, and that just the way you brought
broke it down was so, so good. It's so helpful. Jason, who is this book for? This book is for
literally anybody who is experiencing some kind of change in their lives. It is mostly work
focused, I will admit, but like I just said, I think that the things that you learn that you can
apply in work, you can really take to any other part of your life. I wrote it because
everybody is going through massive change right now in some way. The ripple effects of the pandemic
are nowhere near over and possibly will not be over in our lifetimes.
And that means that we're going to be constantly, constantly feeling disrupted,
that what we want is going to change.
What is available to us is going to change.
And I wanted to give people a guide for ways to think about that
and navigate that for themselves so that they can realize they're more in control
than they think they are.
And that's control is a beautiful thing in the moments where you have it fleeting most
often, but really getting to that place, like you said, where you're embracing it instead of
panicking, is the whole key. Build for tomorrow, an action plan for embracing change,
adapting fast, and future futureing your career by Jason Pfeiffer. Where can we find the book?
Where can we find you? You can find Build for Tomorrow, anywhere you find books. So Amazon is a place
that you can find books. Barnes & Noble is a place you can find books. If you cannot remember those,
then Jasonfeiffer.com slash book, also a fine place to find the book, but anywhere you find books,
is built for tomorrow. And then I'd love for people to reach out directly to me. I am on
Instagram at, Hey, Fyfer, and I'm on LinkedIn, very active, as I know you are, Jason Fyfer.
And I make it a commitment to respond to everybody. So if you heard this, I know, you're making a
face, but it's a, but, but, uh, that's a lot. It's a lot. I know, it's a lot. But I, but there's a reason,
there's a reason I do it. And the reason I do it is because I find that even though it can be time
consuming. When people reach out to me, I mean, I'm sure that this has happened with you, too,
right? People reach out, they say something. They give me a comment on something. I heard you
on this podcast, whatever it is. And then if I respond to them, they will respond immediately and
they'll say, oh my gosh, I didn't expect to hear from you. And I find that this small gesture,
which for me is, you know, it's not that much. It's a moment of my time where I'm standing in
in front of the microwave waiting for, you know, the pizza to reheat or something. But for somebody
else that small gesture of mine is really big and one i just find that to be a powerful it's just a
powerful thing to be able to do but then two frankly strategically if you connect with somebody if you
allow somebody to feel heard they are your fan for life it is just the greatest though not that
scalable audience building tool that i've ever found and so i know the number one thing that people want
is to feel heard and i and i want to validate that so anyway that's why i respond to everybody
even though sometimes it takes me a little time.
And so, anyway, point is, if you hear this podcast,
if you pick up this book, if you have a thought, a comment,
drop me a line, DM, I will respond.
Well, I will have all those links and all of Jason's handles
in the show notes so you can go check them out,
but go grab the book, build for tomorrow.
We are all dealing with a lot of change,
just like you mentioned.
I'm so grateful you wrote this book,
and thank you for all the tips today, Jason.
Oh, thank you, and good luck on your move.
a year right back at you and good luck to everybody who's listening dealing with change out there until
next week keep creating your confidence i decided to change that dynamic i could have been more
excited for what you're going to hear start learning and growing inevitably something will happen
no one succeeds alone you don't stop and look around once in a while you could miss it
I'm on this journey with me.
