The Contract You Made With Yourself

When I graduated college, I was going to be a developer. That was the plan. I had the degree. I had the job. I was on Wall Street writing code.

Then I watched the people around me work, and realized something uncomfortable: I didn't love programming enough to be exceptional at it. I was competent. But loving something enough to be great at it is different from being competent, and I could see the gap.

So I pivoted. Infrastructure work—still technical, not programming. I founded a company and ran it for thirteen years. I pivoted again to corporate storytelling as an entrepreneur, which failed in most respects. But that failure gave me enough credibility to get a marketing role at a startup, which led me to analyst relations, which is what I do now.

Every pivot felt like failure. Each one looked, at least temporarily, like giving up on something I'd committed to. None felt like progress while I was living through it. Looking back though, the through-line is obvious. I always loved writing and storytelling. I always loved technology. I always gravitated toward connecting dots across functions and making complex things clear.

Today I write and communicate about technology.

The roles kept changing. What was underneath them never did.

I keep thinking about this because I keep having the same conversation.

Not with the same person. Different people, different stages, different industries. Different career stages. But the conversation is remarkably similar. 

Sometimes it's with someone who's hit a wall and knows it. More often, it's with someone who, by most visible measures, looks like they're on track. They have a title that means something, or they're building toward one. They've made real progress. People around them would describe them as successful, or at least headed there.

And they're stuck. 

Not stuck in the way that shows up on a résumé. Stuck in the way that shows up at 11pm when you're not busy enough to ignore it. The feeling that something doesn't quite line up—that the direction they're headed is the one they chose years ago, and they're no longer sure it's the right one. But changing course feels irresponsible.
Or wasteful. Or like failure. So they keep going.

The other version of the conversation involves comparison. A peer from the same starting point appears to be further ahead. Better title. Bigger role. More visible success. The question becomes: What did they do right that I didn't?

These two tensions—the contract you made with your younger self and the score on someone else's scoreboard—are closer to each other than they look.

The Contract

Years ago, I wrote an essay called 12 Essential Principles For A Long and Happy Marriage. The twelfth principle—the hardest one—is this: be willing to renegotiate the contract.

When my wife and I met, she was 20 and I was 21. We had expectations—about careers, about roles, about what our life would look like. Some of them were explicit. Most were implied. But spoken or not, those expectations formed the contract. Over time, things changed. Kids. Careers that zigged when we expected them to zag. Interests that evolved. The contract wasn't wrong. It just stopped fitting.

One way I've seen marriages get into trouble is when one or both people hold the other to a version of the deal that no longer reflects who they've become. "I thought you were going to be this kind of person." "I thought we agreed on that." The original contract made sense at the time. It was negotiated by two people who no longer exist in quite the same form.

Careers work the same way.

At some point—22, 25, 30—you put a marker down the road and said: that's where I'm headed. A career in finance. A startup. A director title by 35. Whatever it was, that marker served you. It gave you direction when you needed it. It helped you make decisions, say no to distractions, and keep moving.

But along the way, you changed. Life happened—relationships, responsibilities, interests you didn't expect.  Successes and disappointments that reshaped your priorities. The marker is still out there, but the person who planted it isn't the same person walking toward it. Renegotiating the contract isn't giving up on your goals. It's recognizing that the version of you who set them was  working with different information. Success is allowed to evolve as you do.

Many people spend more time defending old decisions than questioning whether those decisions still fit.  Changing course feels like an admission that you got it wrong. More often, it's simply acknowledging that circumstances changed.

The mindset that got you here—the hunger, the fear of falling behind, the refusal to fail—served you. It got you through school, through early career chaos, through the years where you had to prove you belonged. 

But there comes a point when that mindset stops being fuel and starts becoming weight. Because it worked for so long, you don't question it.

At some point, you have to thank that part of yourself for getting you this far—and let it go.

Someone Else's Scoreboard

The comparison trap is harder to talk about because nobody wants to admit they're doing it.

But they are. Someone you came up with has the title, the role, the visible momentum. From the outside, it looks like they're winning.

And you're sitting there thinking: we started in the same place. We have similar profiles. What did they do that I didn't?

I've written about this before. In Any Game but Chess, I used a line from Warren Buffett: "Somebody said, 'How do you beat Bobby Fischer?' You play him in any game except chess." That issue was about companies competing on someone else's terms. The same principle applies to careers.

Your situation is unique. Your experience, your strengths, your ambitions, your needs, your constraints, your obligations, your definition of what a good life looks like—none of it maps neatly onto someone else's, even if the career path looks identical from the outside. Comparing yourself to a peer who appears further ahead is playing chess on their board.

The energy spent tracking someone else's progress is frequently a sign that your own definition of success isn't fully formed.

Because if you knew what you wanted, you wouldn't care what they were doing. 

When you're clear on what you're optimizing for, other people's scorecards become less interesting.

There's a scene in The Italian Job where the bad guy steals the gold from his own crew. What does he do with it? He buys everyone else's dream—the great stereo, the fast cars—because he doesn't have one of his own. "No imagination." That's what happens when you borrow someone else's goals. You end up chasing a version of success that was never yours to begin with.

And you may not want everything that comes with what they have. The travel schedule. The hours. The tradeoffs they made that you can't see from the outside. 

You're comparing your interior to their exterior.

That comparison rarely produces anything useful.

You know what you don't want. That's a start, but it's not as valuable as knowing what you do want. One keeps you from making mistakes. The other actually gets you somewhere.

Foundation and Campaign

In my work with companies, I spend a lot of time on the distinction between foundational narrative and campaigns. The foundational narrative is who you are—why you exist, what you believe, what makes you different. 

Campaigns are what you do to be visible, to compete, to respond to the market. They're tactical and they change. The foundation shouldn't. The foundational narrative is what everything else connects back to.

The failure mode I see repeatedly is when companies lose the foundation and start operating entirely from campaigns. More launches. More features. More activity—none of it anchored to the story underneath. 

Lots of motion. Less meaning.

The same thing happens in careers. A title is a campaign. A specific role is a campaign. A salary target, a "director by 35" goal, a plan to break into a particular industry—those are all campaigns. They're not wrong. But they're not the foundation.

In The Career Rubric Disappeared, I introduced the Ideal Work Profile—the IWP. It's a working hypothesis about the kind of work that fits you, tested across roles and refined over time. Each role is a prototype. What you're building is the pattern underneath—how you think, what problems energize you, what kind of contribution you keep making regardless of the title on your LinkedIn profile. That pattern likely reflects your foundational narrative. The roles and goals are campaigns built on top of it.

Here's why renegotiation feels so hard: people mistake their campaigns for their foundation. The goal you set at 25 has been your North Star for so long that it feels like identity. Changing it doesn't feel like updating a plan. It feels like losing yourself. So you keep grinding toward a marker you're no longer sure about, because the alternative feels like admitting you don't know who you are without it.

But the foundation is more durable than any campaign. Renegotiating the contract isn't abandoning who you are. It's clearing away the campaigns that no longer fit so the foundation can surface. That's the part you don't renegotiate. That's the part you build from.

The Messy Middle

I'm an angel investor in a company called Cheersy, a day-of wedding coordinator marketplace. The founder, Amy Shack Egan, recently posted about her career path in a way that captures something I've been trying to articulate.

She graduated with an offer from a top PR agency. She turned it down. She backpacked through Europe instead, then came home and took a string of unglamorous jobs—social media for a t-shirt startup at $30 an hour, nannying, opening shifts at a bakery. At Thanksgiving, explaining what she was doing required context.

To many of the people around her, her ambition looked misplaced. Why not a corporate job? Law school? Something stable?

She had a feeling she was headed somewhere, even if she couldn't explain where. And those years—the ones that looked messy from the outside—built the foundation for what she eventually created.

Her line that stays with me:

That's true of companies.

It's true of careers.

Berkson's Bits

Authentic listening is a critical skill. It means listening with genuine interest, no agenda, and not being over eager to jump in with your thoughts or opinions. I've found people tend to share the most important or interesting tidbits at the end of what they have to say, not the beginning. Let them get there.

What I'm Listening To...

The first live concert I attended was Styx at Madison Square Garden in 1981. It was their Paradise Theater tour. I didn’t love that album, but what I wanted to hear was Borrowed Time. I loved the quiet build up to screaming electric guitar blasting in at about 40 seconds into the song. Still like it. Hope you do too.

The renegotiation doesn't come with a clean narrative. You don't get to skip the period where it doesn't make sense yet—to you or to anyone watching. The people I talk to who are struggling with this aren't struggling because they lack talent or direction. They're struggling because they're in the middle of the story, before it resolves, and they want to know it's going to work out before they commit to the next chapter.

I can't promise that. Nobody can. 

The people who stay loyal to a contract that no longer fits often end up somewhere that looks right from the outside and feels wrong from the inside.

And the ones who renegotiate? They usually spend time in a messy middle—where the story doesn't make sense yet, where the next move can't be fully explained, and where the outcome isn't guaranteed.

That's the uncomfortable part.

But most meaningful pivots look irrational before they look inevitable.

Looking forward to continuing the conversation...

Alan