A version of this article has appeared as a cover interview of the February issue of Cloud961 magazine. You can read the full issue here.
August 21, 2026
Things I Changed My Mind About
I've always found changing my mind slightly uncomfortable. There is a strange pressure, especially as you get older, to appear consistent. We are encouraged to have strong opi…
I've always found changing my mind slightly uncomfortable. There is a strange pressure, especially as you get older, to appear consistent. We are encouraged to have strong opinions, defend them confidently, and stand by what we said before. Changing your mind can sometimes look like weakness, indecision, or a lack of conviction. I've come to see it differently. Changing your mind is often evidence that you learned something.
Some of the opinions I had in my twenties feel almost foreign to me now. Others have simply become more nuanced. There are things I once considered extremely important that barely register anymore, and things I didn't understand at all that have become central to how I think about work and life. I'm sure I'll change my mind about many of these things again. That's probably the point.
I changed my mind about having a five-year plan
For a long time, I thought ambitious people were supposed to know where they were going. You picked a direction, established a few milestones, and worked backward from them. The idea was that if you were disciplined enough, you could more or less design your future.
I still believe in having goals. I just don't believe in pretending that you can predict your life accurately five years from now. Over the course of my career, some of the most interesting opportunities came from directions I couldn't have predicted. Jobs appeared that weren't part of the plan. Projects introduced me to people and industries I hadn't expected to work with. Circumstances changed. Priorities changed. I changed.
A five-year plan assumes that the person making the plan and the person executing it will have roughly the same interests, priorities, opportunities, and circumstances. They won't. I still think it's useful to have a direction, but I don't think you need a detailed map.
I changed my mind about job titles
I used to care much more about titles than I do now. There is something seductive about a good title. It feels like a public measurement of progress. Manager sounds better than Specialist. Director sounds better than Manager. Head of something sounds better still.
But after enough time in the workplace, you realize that titles are often less meaningful than the work attached to them. I've seen people with impressive titles who had very little influence, and people with relatively modest titles who were the person everyone relied on when something important needed to get done.
A title can tell you where someone sits on an organizational chart. It doesn't necessarily tell you how capable they are, how much they contribute, or how much responsibility they actually carry. These days, I'm much more interested in what someone does than what their email signature says.
I changed my mind about saying yes to every opportunity
Earlier in my career, I thought opportunities were things you were supposed to take. If someone offered you an interesting project, a new client, a better role, or an opportunity to work with someone impressive, the instinct was to say yes before somebody else did. There was a certain logic to it. Early in your career, you need experience, you need to meet people, and you need to learn. Saying yes can create opportunities you couldn't have planned for.
But eventually, saying yes to everything becomes its own problem. Every yes consumes something: time, attention, energy, and focus. As you become more experienced, your most valuable resource isn't necessarily your ability to do more. It's your ability to decide what deserves your attention.
I've learned that an opportunity can be genuinely good and still be wrong for you. That's a surprisingly important distinction. Not every interesting project needs to become your project, and not every door that opens needs to be walked through.
I changed my mind about specialization
For a long time, I thought the safest career strategy was to become exceptionally good at one thing. Specialization makes sense. The more specific your expertise becomes, the more valuable it can be. In a world where everyone is competing for attention, being known for something is useful.
But my own career went in the opposite direction. I've moved between marketing, communications, growth, strategy, content, digital, consulting, management, and different industries. For a while, I worried that this made my career look scattered.
Eventually, I realized that the different pieces were connected. Understanding marketing made me better at growth. Working with different businesses made me better at strategy. Working across cultures made me better at communication. Managing people made me better at understanding how organizations actually work.
I've become less interested in being the world's best person at one narrow thing and more interested in being someone who can walk into an unfamiliar problem and figure out how to make sense of it. That may not be traditional specialization, but it's a skill too.
I changed my mind about productivity
I used to think being productive meant doing more. More emails answered, more projects completed, more meetings attended, and more tasks crossed off the list. There is an entire industry built around convincing us that the solution to having too much to do is becoming better at doing things.
I'm less convinced.
At some point, you realize that you can become extremely efficient at doing things that don't actually matter. The more senior you become, the more important the question becomes: should this be done at all?
I've started to think of productivity less as maximizing output and more as protecting attention. Some of the best work I've done has happened when I had enough uninterrupted time to think. Some of the worst decisions I've made happened when I was moving quickly simply because everything felt urgent.
Being busy can create the feeling of progress without necessarily producing it. I wish I'd understood that earlier.
I changed my mind about networking
I used to think networking meant meeting people who could help your career. That made the whole concept feel transactional. You meet someone, exchange contact details, connect on LinkedIn, and occasionally message them while wondering somewhere in the back of your mind whether the relationship might eventually lead to a job, a client, or an introduction.
I don't think about networking that way anymore.
The most valuable professional relationships I've built rarely started with a calculation about what the other person could do for me. They started because we enjoyed talking to each other, worked well together, were curious about similar things, or simply helped each other when we could.
Some relationships have lasted for years without either person ever needing anything from the other. That's probably a better definition of networking. Build relationships with people you actually like and respect, and the professional value tends to follow naturally.
I changed my mind about money
Money matters. I don't think pretending otherwise is particularly useful. Financial security gives you choices. It can reduce stress, create independence, allow you to help people you care about, and give you the ability to walk away from situations that aren't right for you.
But I used to think that earning more money would automatically make me feel more successful. It doesn't.
At some point, you start asking what the additional money is actually buying you. More freedom? Great. More security? Valuable. More options? Absolutely. But if you're simply exchanging more of your time, energy, and peace of mind for a larger number in a bank account, the calculation becomes more complicated.
I've become much more interested in the relationship between money and freedom than money and status. Those are not the same thing.
I changed my mind about being right
This one took me longer than it should have. I used to enjoy being right. I think most intelligent people do, at least to some extent. There is satisfaction in having the correct answer, especially when you had to argue for it.
But being right isn't always the most useful outcome.
Sometimes the person with the best idea isn't the person who explains it most forcefully. Sometimes you need to let someone reach a conclusion themselves. Sometimes you need to accept that your original idea wasn't as good as you thought. And sometimes two people can have different perspectives without one of them being stupid or wrong.
Experience has made me less interested in winning arguments and more interested in understanding why someone sees things differently. I haven't completely mastered this one, but I'm better at it than I used to be.
I changed my mind about success
This might be the biggest one.
I used to have a fairly conventional idea of success. Build a strong career, earn more, take on bigger responsibilities, work with better-known companies, and keep moving forward. There's nothing wrong with any of that.
But eventually, I started asking a different question: forward toward what?
A career can keep progressing indefinitely. There is always another title, another salary, another company, and another goal. If you're not careful, you can spend your entire life achieving things without ever stopping to ask whether you actually wanted them.
My definition of success has become much more personal. I want to do interesting work, keep learning, have enough financial freedom to make decisions without constantly worrying about money, work with people I respect, have time outside of work, and have the freedom to change direction when something no longer makes sense.
That definition probably wouldn't have impressed my younger self very much. Today, it sounds pretty good.
I changed my mind about certainty
I used to think confidence meant knowing what you were doing. Now I think confidence can sometimes mean knowing that you don't.
There is a difference between being uncertain and being incapable. You can be very good at what you do and still not know what comes next. You can make a thoughtful decision without knowing whether it will work. You can start something without having the entire journey figured out.
Some of the biggest changes in my life happened when I didn't have a clear answer. I've become more comfortable with that, not because uncertainty became less uncomfortable, but because I've learned that certainty is often an illusion anyway.
I changed my mind about changing my mind
Perhaps that's the biggest lesson.
I used to think changing your mind meant that your previous opinion was wrong. Now I think it can simply mean that you have more information.
The person I was ten years ago made decisions with the knowledge, experience, priorities, and circumstances he had at the time. I don't need to be embarrassed by the things he believed. He didn't know what I know now. And ten years from now, I may look back at some of the things I believe today and think the same thing about myself.
That's okay.
I'd rather be someone who can say, "I used to think that, but I don't anymore," than someone who protects an old opinion simply because admitting that they've changed feels uncomfortable.
Maybe growing up is partly the process of becoming less attached to being the person you thought you were supposed to be. You learn, you experience things, you make mistakes, you see more of the world, and you meet people who challenge your assumptions. Eventually, you change your mind.
I don't think that's inconsistency. I think that's education.
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