How come I ended up with anxiety or financially broke a couple of times in my career as an entrepreneur?
I’ve asked myself this question more than once. Funnily enough, the mistakes I’ve made have been more about soft skills than technical ones. That says a lot about what being an entrepreneur really is. At the end of the day, all we see in a person is a reflection of their unique blend of traits: hard work, resilience, communication skills, empathy, leadership, and so much more.
So, here’s my list of my top five worst mistakes for your entertainment—consider it a delightful self-roast. Believe me, the full list is much longer, but let’s start with these:
1. Learning from my customer in a different country
In my first company, I was launching a product for the U.S. market. But since U.S. ad costs were way too expensive for the limited funds I had raised, I decided to test my hypothesis and run ads in Latin America instead. Sure, it was cheaper, but it was also a terrible idea because the two audiences had completely different needs.
The results of this experiment weren’t conclusive because the product was meant to serve U.S. customers, not Latin Americans. Cultural differences, buying behavior, and customer needs vary significantly across regions, and I missed the opportunity to learn about my real target market.
The result? I blew all my money, and naturally, that company didn’t make it. Lesson learned: If your goal in the early stage is to learn about your customer, focus on your actual target audience.
2. Not giving myself enough time to rest
I came from the “old-school” Silicon Valley entrepreneur culture of the 2010s—where burning out was considered a badge of honor. The startup mentality back then was all about “hustle 24/7” and “if you’re an entrepreneur, that’s your entire identity.”
This lack of balance in my early twenties left me with high levels of anxiety and the belief that building a company meant sacrificing personal life and well-being. Here’s the truth: It doesn’t.
You can create a life for yourself and your team that prioritizes balance. Rest is essential if you want to perform at your best, align with your purpose, and inspire others. A burnout entrepreneur isn’t a leader anyone should emulate.
3. Not setting boundaries
I was terrible at setting boundaries, both in my personal life and in my business. It turns out the two are deeply connected.
In practical terms, you can establish boundaries in your company by having clear, written rules, setting well-defined contracts with clients and employees, and addressing any discomfort immediately. It’s your freaking company—you should feel comfortable and confident running it.
Remember, you created your business not only to serve your clients but also to find happiness and purpose for yourself. Make it count.
4. Doubting myself
For too long, I believed I wasn’t good enough to tackle big challenges, and that self-doubt kept me from pursuing amazing opportunities. Even worse, when I did take on new challenges while doubting myself, I felt anxious about the future and unsure of my abilities.
Now, whenever self-doubt creeps in, I pause, take a deep breath, and spend five minutes visualizing myself smashing every challenge ahead. This simple practice shifts my mindset, bringing me back to the land of opportunities and reminding me of my power.
5. Quitting too late
The more time, money, or effort you invest into something, the harder it is to walk away. That’s because we instinctively focus on the losses we’ve already incurred. But here’s the kicker: We rarely consider the losses we’ll face if we keep going down the wrong path.
Losses from the past can’t be undone—they’re done. But you can focus on the future and start creating new abundance for yourself. This was one of the hardest lessons for me to learn because our culture tends to glorify perseverance and stigmatize quitting.
I learned a lot about this concept from the world-renowned poker player Annie Duke and her book Quit. She says, “If you’re certain that quitting is the right decision, you’ve waited too long.” That one hit me hard.
Entrepreneurship isn’t just about hard skills or technical know-how—it’s about self-awareness, resilience, and constantly learning from your mistakes. The journey is messy, full of missteps, but also rich with growth and transformation. So, here’s to embracing our mistakes, roasting ourselves a little, and moving forward with purpose and joy 🥹
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