Five years ago I was twenty-three. I’d traveled a decent amount, built a few things, had strong opinions about everything. I thought I knew what I was doing. I thought certainty was a sign of intelligence.
I was wrong about that, and wrong about a lot of other things too.
This is an attempt to document the shifts. Not because my current beliefs are final — they obviously aren’t — but because I think the act of noticing what’s changed is one of the more useful exercises a person can do. It keeps you honest. It reminds you that the thing you’re absolutely sure about right now might look naive in another five years.
Here’s where I’ve landed, for now.
Speed matters more than perfection
Five years ago I believed in the finished product. The polished deck. The fully baked idea. I would spend weeks refining something before showing it to anyone, because I didn’t want to look like I hadn’t thought it through.
Now I believe that speed is its own kind of quality. Not rushed, careless speed — but the discipline of shipping something real before you’ve fallen in love with your own version of it. The fastest way to learn whether an idea works is to put it in front of someone. Every day you spend polishing in private is a day you could have spent learning in public.
At PipelineRoad, we build things in weeks that used to take us months. Not because we’ve gotten sloppier, but because we’ve gotten better at distinguishing between what needs to be right on day one and what can evolve.
The shift was partly practical, but mostly psychological. I had to get over the fear of being seen mid-process. That fear cost me more time than any actual mistake ever did.
Most advice is autobiography
I used to consume business advice like it was scripture. Podcasts, books, Twitter threads, all of it. I’d hear someone say “never raise funding” or “always raise funding” or “fire fast” or “give people second chances” and I’d file it away as truth.
Now I understand that almost all advice is just someone describing what worked for them, in their specific context, with their specific advantages and constraints. It’s autobiography disguised as instruction.
This doesn’t make advice useless. It makes it data. One person’s experience, filtered through their biases, delivered with the confidence of universal law. Your job is to extract the signal and discard the packaging.
The advice that’s actually changed my life has almost never come from people trying to give advice. It’s come from watching how certain people operate — the decisions they make, the things they prioritize, the stuff they quietly ignore.
Relationships are the whole game
This one embarrasses me a little because it’s so obvious. But five years ago I was much more focused on skills, output, personal capability. I thought success was mostly about being good at things.
It is partly about being good at things. But the distribution of opportunity is almost entirely relational. The clients we’ve gotten at PipelineRoad, the partnerships that have mattered, the team members who’ve made the biggest difference — every single one came through a relationship. Not a cold email. Not a LinkedIn post. A human connection, built over time, that eventually led somewhere.
I don’t mean this in a networking-event, collect-business-cards way. That stuff is mostly theater. I mean genuine relationships where you actually care about the other person’s success. Where you stay in touch when there’s nothing to sell. Where you show up when it’s inconvenient.
The compounding returns on real relationships make everything else look like a rounding error.
You don’t need to have an opinion on everything
This was a big one. I used to feel obligated to have a take on whatever was happening — in the news, in tech, in culture. Social media rewards people who have opinions, and I confused that reward with value.
Now I’m comfortable saying “I don’t know enough about that to have a view.” It’s one of the most liberating sentences in the English language.
Having fewer opinions has paradoxically made my actual opinions better. When I do take a position, it’s because I’ve thought about it. Not because someone asked and I felt pressure to perform certainty.
I’ve noticed that the people I admire most are surprisingly quiet on most topics and surprisingly specific on the few they’ve mastered. That’s not timidity. That’s allocation of attention.
Money is a tool, not a score
Five years ago I thought about money the way most ambitious young people do — as a measure of progress. More money meant things were going well. The number was the signal.
I still think financial success matters. You can’t build anything meaningful if you’re constantly worried about rent. But somewhere along the way, I stopped seeing money as validation and started seeing it as optionality.
The point of money is to buy freedom. Freedom to work on problems you find interesting. Freedom to say no to clients or projects that don’t fit. Freedom to take a month and travel without your business collapsing. Freedom to hire people you trust and pay them well.
When I started evaluating financial decisions through the lens of “does this increase my freedom?” instead of “does this increase my number?”, everything got clearer. Some high-revenue opportunities decrease your freedom. Some lower-revenue paths expand it enormously.
Travel changes you whether you want it to or not
I used to think of travel as something you did to have experiences. To see things. To check places off a list.
Now I understand that travel is a confrontation with your own assumptions. Every country you visit challenges something you believed was universal but was actually just local. The way you think about time, hospitality, food, ambition, family, success — all of it gets pressure-tested when you’re somewhere that does it differently.
I didn’t choose to become more patient. Spending three weeks in places where things move slowly just made me that way. I didn’t decide to care less about material status. Living out of a backpack in countries where people are happy with almost nothing recalibrated my sense of what matters.
The changes aren’t always comfortable. Coming home after extended travel can feel disorienting because you’re not quite the same person who left. But I’ve never regretted a single trip, and I’ve regretted plenty of things I stayed home to do instead.
Small teams beat big ones
I used to think scale was the goal. More people, more clients, more everything. Growth as the default setting.
Now I believe that small, excellent teams outperform large, mediocre ones in almost every context. Five people who are fully aligned, deeply skilled, and genuinely invested will produce more than twenty people who are sort-of-there.
At PipelineRoad, we’ve deliberately stayed small. We serve eight clients across eleven brands, and we do it with a team of five. This is not a limitation we’re trying to overcome. It’s a choice we’ve made because the work is better when everyone is close to it.
The pressure to grow headcount is constant and mostly external. Investors want it. Peers expect it. The narrative of success in business is a narrative of expansion. But some of the most profitable, most enjoyable, most impactful companies I’ve encountered are small on purpose.
Health is not a category. It’s the foundation.
I didn’t take health seriously until I watched it fail in people I care about. That’s a stupid way to learn the lesson, but apparently it’s a common one.
Five years ago, exercise was something I did when I had time. Sleep was something I sacrificed to get more done. Food was whatever was convenient.
Now I treat sleep, exercise, and nutrition as non-negotiable infrastructure. Not because I’m disciplined — I’m really not — but because I’ve seen the math. An hour of exercise doesn’t cost an hour of work. It buys back two or three hours of sharper thinking. Seven hours of sleep doesn’t lose you time. It makes the remaining seventeen hours actually functional.
The people I know who sustain high performance over years, not months, all have this figured out. It’s not sexy. Nobody’s posting about their bedtime. But it’s the foundation everything else sits on.
Being wrong is not the same as being stupid
This is the belief change that underpins all the others. Five years ago, being wrong felt like a character flaw. If I’d taken a position and it turned out to be incorrect, my instinct was to defend it, minimize it, or quietly pretend it never happened.
Now I think being wrong is just information. It means your model was incomplete. Update the model, move on. The people who can’t do this — who cling to positions because admitting error feels like weakness — are the people who stop growing.
I’ve been wrong about business strategies, about people, about markets, about my own capabilities. Each time, the wrongness taught me something the rightness never could have.
The incomplete list
I want to be clear: this is not a finished worldview. These are waypoints. I expect that five years from now, I’ll reread this and cringe at some of it. I’ll have abandoned beliefs I’m currently sure about and adopted ones I can’t yet imagine.
That’s the whole point. The person who believes the same things at thirty-three that they believed at twenty-three has either figured out everything early or learned nothing late. And the odds heavily favor the second option.
The only belief I’m fairly confident will survive is this one: stay curious, stay uncertain, and pay attention to what changes. The shifts are where the learning lives.