The 5 Leadership Lessons I Wish Someone Told Me at 25

There’s a version of this post that starts with a TED Talk clip or a business school case study. This is not that version. I’m writing this as someone who built a company from $1.5 million in revenue to $15 million, led teams through recessions and market collapses, and made enough mistakes to know what actually matters when you’re responsible for other people’s livelihoods.

These are the five things I wish someone had told me when I was 25 and just starting to figure out what leadership actually means.

1. Your job is not to have all the answers

When I started growing Penebaker Enterprises, I thought leadership meant knowing more than everyone else in the room. If someone asked a question I couldn’t answer, I felt like I had failed at my job. So I spent enormous energy projecting confidence I didn’t always have, and very little energy asking the questions I should have been asking.

It took years to understand that the best leaders aren’t the ones with all the answers. They’re the ones who know which questions to ask and who to ask them to. The moment I started leading by asking instead of telling, the quality of my decisions improved dramatically. People on the ground always know things you don’t. Your job is to create an environment where they’ll tell you.

If I could go back to 25-year-old me, I’d say: spend less time preparing the answer and more time preparing the question. The former makes you look smart. The latter makes you actually effective.

2. Culture is not what you say it is

I used to think culture was the values you posted on the wall or the mission statement you recited at all-hands meetings. I learned the hard way that culture is what happens when no one thinks you’re watching. It’s the behavior that gets rewarded, tolerated, or ignored. It’s how your team treats clients when a job goes wrong. It’s whether your managers tell the truth when the numbers don’t look good.

At Penebaker Enterprises I once had a supervisor who consistently hit his numbers but was a nightmare to work with. People dreaded reporting to him. When I kept him because of his production, I sent a message to the whole company about what I actually valued. That decision cost me more in culture damage than his output was worth.

Culture is built through the decisions leaders make under pressure, not through the speeches they give when things are going well. If you want to know what your culture actually is, watch what happens when someone makes a mistake. Do people hide it or surface it? That answer will tell you everything.

3. Hard conversations are a form of respect

Leaders avoid hard conversations for all kinds of reasons. They don’t want to hurt someone’s feelings. They hope the problem will resolve itself. They don’t feel ready. The result is almost always that a problem that could have been solved in a 20-minute conversation becomes a crisis that takes months to address.

I’ve seen this pattern repeat across more than two decades of leading teams. People know when they are underperforming. Most of them want someone to tell them directly so they can fix it. Avoiding the conversation doesn’t spare their feelings. It just leaves them in limbo, uncertain about where they stand, and unable to improve because no one has told them what improvement looks like. Research consistently shows that many leaders struggle with direct feedback conversations, often avoiding them even when the situation calls for it.

The person I have the most respect for as a leader is the one who told me, clearly and early, that a strategy I was excited about was not going to work. He was right. And he saved me from a decision that would have cost me real money and real credibility. That’s what direct feedback looks like when it comes from a place of respect. It’s a gift.

4. The work you do on yourself matters as much as the work you do on the business

In my twenties and early thirties, I treated personal development as a luxury. Something you did when you had time, which meant never. I was too busy running the business to think about how I was showing up as a leader, a communicator, a decision-maker.

It wasn’t until I hit a real ceiling, a point where the business had grown to a level my existing skills couldn’t sustain, that I understood the connection. Every limit I was running into as a company was a reflection of a limit in me. The bottleneck was always at the top. I started investing in coaching, in understanding how I processed conflict, how I communicated under pressure, how I made decisions when I was stressed. That investment returned more than any piece of equipment I ever bought.

The business you’re building will only scale as far as you scale first. That’s not motivational poster language. It’s practical truth.

5. Resilience is not the absence of struggle, it’s what you do with it

The most dangerous thing about being a leader is how isolating it can become. You don’t want to show vulnerability to your team because you’re supposed to be the stable one. You don’t want to burden your family because they’re already dealing with the ripple effects of your work. So you carry things alone that would be a lot lighter if you weren’t trying to carry them by yourself.

The leaders I admire most aren’t the ones who never struggled. They’re the ones who struggled and found a way to talk about it honestly. Who built the support structures, the advisors, the mentors, the therapists, the trusted peers, that made them sustainable over the long run. Resilience is not stoicism. It’s not pretending you’re fine when you’re not. It’s having the infrastructure to process hard things and come back to your team clear-headed and present.

I talk about this because I know what the alternative looks like. I’ve seen leaders burn themselves out chasing a definition of strength that doesn’t serve them or the people who depend on them. That is not what we need more of. We need leaders who are honest about the weight they carry and smart enough to find ways to carry it without breaking.

What I know now that I didn’t know then

Leadership isn’t a destination. It’s a practice. And the lessons that actually matter don’t come from books or conferences. They come from showing up every day and choosing to be honest with yourself and the people you lead about what’s working and what isn’t.

If I could go back and give the 25-year-old version of me one piece of advice, it would be this: get comfortable being wrong, get good at asking for help, and stop waiting until you feel ready. You will never feel fully ready. Lead anyway.

For more on how these lessons show up in real business situations, read my pillar page on leadership under pressure.

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Last updated: June 28, 2026