Note to my slightly older self

My previous article was a note for my 20+ year old self. This one’s for 30+ year old me after surviving that phase. You know how to code, communicate, and navigate office politics. You’ve built things that actually shipped.

But now you’re staring at a different challenge: How do you move from being good at your job to actually leading? How do you balance ambition with the creeping realization that you can’t do it all?

Welcome to mid-career - where the rules change and nobody sends you a memo about it. Here’s my six rules:

1. Lead with vision, not tasks

2. Do the next job now

3. Own failures publicly

4. You’re your own safety net

5. One miracle per project

6. Define success yourself

(Note: This section is written from a perspective of someone who chose the manager track, but senior ICs are also leaders)

Managers keep things running. Leaders change where things are going.

There’s this moment in every career where you realize you’re the adult in the room. No one’s coming to save the project. The decision is yours. The team is looking at you.

I learned this the hard way. One team I managed grew complacent - happy to hit their OKRs and then... nothing. Meanwhile, a smaller, scrappier team was both happier and more productive. The difference? Vision.

Paint the destination, not the path. Tell your team you’re building the fastest X in the world. Don’t dictate how. Let them surprise you with solutions you never imagined. Your mission is what you’re doing today. Vision is where you’re headed - and it needs to be extreme enough to excite.

Coach, don’t command. Bill Campbell coached Steve Jobs and Eric Schmidt. His secret? He treated executives like players who needed development, not resources to be managed. Ask yourself: Did I help someone grow today, or did I just assign tasks?

Make the hard calls. When the team is spinning in endless debate, end it. Not because you’re smarter, but because indecision is worse than an imperfect decision. I once let a stalled product drag on for a year. The delay cost us more than any wrong choice would have.

Reality check: That complacent team I mentioned? I never did transform their culture. I changed orgs before I could effect the change I’d envisioned. Most teammates eventually left. The project still exists, essentially in maintenance mode. Even with the right insight, organizational change takes longer than your or your org’s patience might allow.

Excellence is table stakes. Everyone at your level is excellent.

Early career, doing excellent work gets you promoted. Mid-career? Your manager isn’t thinking about your promotion. They’re thinking about their deliverables, their boss’s priorities, and whatever’s currently on fire.

Want to move up? Make it inevitable:

Act at the next level now. When your skip-level is out, run their staff meeting. When there’s a gap in leadership, step in before anyone asks. I’ve pushed for new ranking systems and products before anyone asked because I could see what was coming. I already had a proposal for the new system with implementation options and what the org might look like even before it was requested.

Have the career conversation quarterly. I learned this one late, but it works: Not “How am I doing?” but “Here’s what I’m working on to prepare for [specific role]. What am I missing?” Force your manager to think about your trajectory four times a year instead of scrambling during review season. If you aren’t prepared to talk about what it takes to get promoted, then don’t expect the promotion.

Document your scope expansion. This is inline with the brag doc - keep a running doc: “Why I’m Already Operating at [Next Level].” Update it whenever you exceed your current role. When promotion discussions happen (which should be quarterly if you follow the above), you’re not making a case - you’re stating facts.

Live at the intersection. Your manager’s top three priorities. Your org’s top three priorities. Find the overlap. Live there. That’s where visibility meets impact - if you work on things that neither your manager, your director, nor your VP cares about, you will have a hard time getting recognition. You can still have your innovation projects, but never forget to pay the bills.

One more thing: If you’ve been doing the next-level job for over a year without the promotion, have a different conversation. Either they promote you, or you promote yourself elsewhere. By not advocating for yourself, you are leaving too much to chance.

How you handle failure becomes organizational DNA.

When you’re an IC, you can fail quietly. That bug in your code? Fix it before anyone notices. But in leadership, your failures are public property. They become water cooler conversations, organizational folklore.

Here’s the counterintuitive truth: Leaders who can’t admit obvious failures destroy trust faster than those who fail spectacularly but own it. Everyone can see when something isn’t working. Pretending otherwise doesn’t make you look strong - it makes you look delusional.

I make it a point to be public about my failures. I lay out where my thinking went wrong, show the flawed assumptions, own the disruption. The response? Team members talk about the trust this builds.

Your wins give you permission to show your losses. Your losses give others permission to take risks. If you have the safety net to fail publicly, you have an obligation to model how to fall and get back up.

Be kind, not nice. Nice leaders celebrate wins loudly and bury losses quietly. Kind leaders celebrate wins generously but own losses personally and publicly. They say “I made this call, here’s where my thinking was flawed, here’s what we’re learning.”

Organizations that only know how to win are brittle. When they eventually lose, they shatter. Organizations that know how to lose - because they’ve watched leaders do it with grace - can take bigger risks, recover faster, and ultimately win bigger.

Your ability to figure things out is your only real safety net.

Mid-career imposter syndrome hits differently. You’re not worried about whether you can code - you’re worried about the politics, the pressure, the responsibility for other people’s careers.

Here’s what I wish someone had told me: You are your own safety net - and once you know this, you can become the anchor for others too.

By now you have: Multiple successful projects to point to, skills marketable anywhere, a network built over years of being helpful without agenda, and most importantly, the experience of having failed, recovered, and lived to tell about it.

That last one matters most.

Try this: List every professional disaster you thought would end your career. The botched presentation. The production outage you caused. The project that didn’t succeed. Now look at where you are. You recovered from every single one. That’s your real resume.

Stop looking for external safety. Reorgs, strategy pivots, management changes. But your ability to figure things out? That’s permanent.

Operational success comes from focus. Focus means that for any project, you get ONE major unknown. Choose it wisely.

When evaluating any initiative, map out everything: technical challenges, resources, timeline, dependencies, org changes. Here’s the rule: You get one “miracle” - one major unknown you’ll need to solve. That’s your innovation space.

Need to invent novel ML features AND build unprecedented infrastructure AND get three separate orgs to collaborate? That’s three miracles. Time to simplify or walk away. For example, when we first proposed a new ranking algorithm for the feed, we only ranked the top card (leaving the rest of the feed ranking intact) to demonstrate that it could do better than the existing algorithm - that simplified the metrics and the implementation.

I’ve watched too many projects spiral because they needed multiple breakthroughs to succeed. The most successful projects weren’t the most ambitious - they found that sweet spot between innovation and realistic execution.

Patience is table stakes. “Overnight successes” in big tech take years. Quick strategy, slow execution. Track small wins, not just final outcomes. Your internal marketing needs to speak to both your team and leadership - learn both languages.

Navigate organizational debt like technical debt. It compounds from avoided decisions. Don’t waste energy fighting it - focus on maintaining momentum despite constraints. Anyone at any level can drive progress with the right motivation.

Innovation isn’t about breakthrough moments. It’s about consistent forward motion while your team navigates complexity.

Work-life balance is a myth. Work-life choices are real.

The conventional wisdom says find balance - that perfect equilibrium where you excel at work and never miss a soccer game. That’s fantasy. Life doesn’t balance. It tilts. Sometimes toward work, sometimes toward family, sometimes toward that project that keeps you up at night because you love it.

Mid-career is when you need to decide what success actually means to you. Not the default path that leads to middle management plateau. Not someone else’s definition that has you checking email during your kid’s recital “but only if urgent.”

Choose your scorecard. Are you optimizing for technical depth? Team development? Schedule flexibility? Geographic freedom? Interesting problems? The corner office? Pick two or three. You can’t have all of them.

Stop apologizing for your choices. Sprint hard on a critical project for three months? Own it. Take a lateral move for better hours when your parent needs care? Own it. Stay late because you’re genuinely excited about what you’re building? Own it.

Re-evaluate regularly. Every few years, audit your choices. The kids grow up. Parents age. Interests shift. The work that felt meaningful at 35 might feel hollow at 45. What got you here won’t get you there - and “there” might not be where you thought you were going.

The framework I use to think about the options: What will I regret more in ten years - trying and failing, or not trying at all?

The most successful people I know didn’t achieve balance. They achieved clarity. They knew what they were optimizing for and made peace with what they weren’t.

Hey, slightly older me.

Mid-career is exactly what it sounds like - the middle. Not the beginning where everything is possible. Not the end where you’re counting down. The messy, complicated middle where you finally have enough experience to know what matters and enough runway to do something about it.

By now you’ve figured out that:

• Leadership is choosing to own the outcomes

• Failure is data, not disaster

• Recognition follows contribution, but only if you make it visible

• One miracle at a time actually works

• Success is whatever you decided it was

The compound effect I wrote about for our younger self? It’s even more powerful now. Except instead of compounding skills, you’re compounding judgment. Instead of building a network, you’re building a legacy. Instead of surviving, you’re selecting.

Years ago: “Can I do this?”
Then: “How do I do this?”
Now: “Is this worth doing?”

Next season: That’s for the next note.

The middle isn’t about having all the answers. It’s about finally asking the right questions. You’re not at the summit - you’re at the point where you can see multiple peaks and choose which one to climb.

So here’s my reminder to you, 30-something self: You have more time than you think, but less than you assume. The choices you make in this middle decade echo louder than anything before or after.

Choose deliberately. Build consciously. Lead authentically.

The endgame note can wait. We’re not there yet.