7 lessons I learned the hard way
Read time: 7 minutes
A few years ago, I walked out of an important meeting feeling like I’d completely messed it up.
I had spent ages preparing, but in completely the wrong way. I’d totally misread the room, I’d overcomplicated my message, and I left with that horrible feeling that I had blown it.
At the time, I felt like a total failure.
But looking back, that one experience taught me so much more than most of the “wins” I’d had up to that point.
We live in a world that celebrates success: promotions, funding rounds, job offers, big announcements.
But my personal reality is that growth typically happens in the messier moments. The setbacks, wrong turns, and uncomfortable meetings actually do a lot more than the highlights.
Across medicine, consulting, and building a startup, the biggest lessons haven’t come from the victories. They’ve come from the mistakes.
Here are some of the ones I’ve made, and what they taught me.
1. Moving quickly without clear direction
When I first started building a startup, I had a lot of energy but very little clarity. I spent countless hours and a significant amount of money working on things that, in hindsight, didn’t really move the business forward.
What I eventually realised is that speed only matters when you’re heading the right way. Running faster in the wrong direction just takes you further away from where you want to go.
The lesson: Test ideas early. Gather feedback. Validate your direction first — then move quickly.
2. Surrounding myself with the wrong people
Early on, I made the mistake of bringing people on without thinking deeply enough about values or alignment. Over time, that created friction and ultimately slowed progress.
I also hugely underestimated how much influence the people around you can have, whether that’s mentors, peers, or even the content you consume. The wrong voices create confusion, whilst the right ones sharpen your thinking.
The lesson: Be intentional about who you spend time with. Choose people who stretch your thinking and move you forward.
3. Staying invisible instead of showing up
For a long time, I kept my head down and actively avoided putting myself out there. I thought sharing online felt very self-indulgent and unnecessary.
What I didn’t realise then was that building a personal brand isn’t about ego. It’s about visibility. It helps people understand what you stand for and opens doors that would otherwise stay closed.
The lesson: Share your journey openly including the wins, setbacks, and lessons along the way. That visibility compounds over time.
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4. Saying yes too often
I used to think saying yes to everything was a sign of my ambition and commitment. In reality, it left me exhausted, burnt out, and constantly stretched too thin.
What I learnt is that every yes carries a cost. It takes time, energy, and focus away from something else. Once I realised that, I became much more deliberate about what I commit to.
The lesson: Protect your time and energy. Default to no unless something feels like a clear yes.
5. Pushing myself beyond healthy limits
There were long periods where I prioritised ambition over everything else. Sleep, health, balance — all of these took a back seat.
Eventually I experienced burnout, which taught me something important: you can’t produce meaningful work when you’re totally depleted.
Looking after yourself isn’t optional. It’s foundational.
The lesson: Build rest and recovery into your schedule intentionally, rather than treating them as something you only earn after working hard.
6. Listening to too many opinions
At one point I tried to absorb advice from everywhere: books, podcasts, mentors, social media. The result was a lot of conflicting ideas and very little progress.
Eventually I realised that more information isn’t always helpful. You have to be selective about what you take in and what you act on.
The lesson: Learn widely, but filter carefully. Keep the advice that fits your context and ignore the rest.
7. Not backing myself enough
Of all the mistakes I’ve made, this one has probably been the most common: holding back. Playing smaller than I should. Assuming I wasn’t ready yet.
But time and again, I’ve realised that we’re usually capable of much more than we believe. Most of us are only scratching the surface of what we can do. Which is actually quite a liberating thought.
The lesson: Back yourself. Aim a little higher than feels comfortable. You’ll often surprise yourself.
The takeaway
Mistakes aren’t the opposite of success, they are part of the process. Each one helps you build experience, resilience, and better judgement. Then over time, those lessons compound.
And often, the moments that feel like setbacks at the time turn out to be the ones that shape you most.
Speak soon,
Dupé
PS: As always, if you’d like deeper support in showing up confidently and growing your personal brand, reply to this email to explore 1:1 coaching or ready to post content.
