36 Lessons for My Younger, Entrepreneurial Self

I turned 36 yesterday (geeze, is that even real?) and with that milestone came a wave of introspection.

Birthdays have a funny way of making you pause, don’t they?

I found myself reflecting on the path I’ve traveled—both the wins that shaped me and the lessons that refined me. Navigating the unpredictable world of entrepreneurship has taught me more than I ever imagined, and as I look back, I can’t help but think about the things I wish I could have told my younger self. The hard-won wisdom, the perspectives that have served me best, and the reminders to stay grounded—these are the 36 lessons I’d pass along, not just to my past self, but to anyone chasing big dreams while trying to build a life they love.

1. An employee mindset will hold you back from entrepreneurial success.

Being your own boss means unlearning the habits of an employee. The safety nets, step-by-step instructions, and “clock-in, clock-out” mentality don’t translate here. Entrepreneurship requires you to think like an owner—taking risks, solving problems independently, and making decisions without always knowing the outcome. It’s scary at first, but it’s also freeing.

2. Your family won’t always understand your path—and that’s okay.

Your parents worked hard and paved the way for your success by modeling traditional career paths. It worked for your siblings and probably made sense for you, too, until you decided to carve out your own route. To them, your path might look dark and unfamiliar, but their confusion doesn’t mean they don’t care. With time, they’ll see the vision you’re building, but in the meantime, trust yourself.

3. You’re not just selling a product—you’re selling a solution.

What you’re offering solves a real problem, and that makes it valuable. Set your pricing accordingly and stand behind it. Remember: it’s not your job to determine whether your solution fits someone’s budget—that’s up to them. Instead, focus on being transparent, delivering your best, and letting your clients decide what aligns with their priorities.

4. Screw perfectionism—mistakes are the secret ingredient to success.

In marketing, we call it A/B testing; in life, it’s just a series of educated guesses. Time is money, and perfectionism will eat up both. Make decisions quickly, test your ideas, and when you mess up (because you will), celebrate the data it gives you. Every failure is a step closer to getting it right.

5. Know the value of your time, and let that guide your decisions.

If your time is worth $100/hour, outsourcing yard work at $40/hour is a no-brainer. What about meal prepping? Accounting? Filter every task through this lens, and don’t feel guilty about delegating or saying no. You can’t do it all, and guess what? You’re not supposed to.

6. Master the art of identifying bottlenecks—and tackle them relentlessly.

Your life and business will always have limiting factors, and your job is to find them and fix them. Sometimes it’s cash flow, but more often, it’s time. If you’re the bottleneck, figure out ways to replace or delegate yourself. Your success will depend on how effectively you can remove obstacles, even if the obstacle is you.

7. To achieve flexibility, embrace flexibility.

The freedom you’re chasing comes with a paradox: you have to be adaptable to get there. Success as an entrepreneur requires constant adjustments—pivoting strategies, changing routines, and rethinking what works for you. True flexibility isn’t handed to you; it’s earned through the willingness to evolve.

8. Never apologize for prioritizing a lifestyle that fuels your productivity and creativity.

Your path might look unconventional to others, but if it creates an environment where you can do your best work, then it’s the right path. You’re not here to meet anyone else’s expectations. Own your choices without guilt—they’re what enable you to thrive.

9. Another person’s success doesn’t diminish your own.

Seeing someone else win can spark doubt, but their achievements aren’t a reflection of your shortcomings. There’s room for everyone at the table, and success is not a zero-sum game. Celebrate their wins as proof of what’s possible, not a measure of what you lack.

10. Refuse to engage in power struggles—you’ve earned your seat at the table.

In this male-dominated industry, you’ll encounter posturing and subtle (or not-so-subtle) power moves meant to undermine your confidence. It’s frustrating, but power plays are generally distractions, not reflections of true talent. Focus on the work that matters and align yourself with people and opportunities that value your contributions. 

11. Growth and success aren’t linear—embrace the ebb and flow.

Some seasons will feel like everything is falling into place, while others will feel like you’re climbing uphill in the dark. Both are part of the journey. Trust that the setbacks and slower seasons are making space for your next big breakthrough. Success is never a straight path, and that’s what makes it worth pursuing.

12. Don’t underestimate the impact your willingness to pursue big, scary dreams will have on your sons.

You’re modeling something extraordinary here. By chasing ambitious goals and facing uncertainty head-on, you’re leaving a legacy of resilience, adaptability, and courage. They’ll grow up inspired by the example of a strong woman leader, learning not only to admire women who lead but to actively support them. In a world increasingly marked by uncertainty, your sons will grow up seeing their parents navigating big scary things first-hand, and will be leaders to the next generation of culture shifters.

13. Your holistic perspective will be your secret weapon in this field.

You’re not just a business owner or tech expert—you’re a wife, mom, artist, provider, developer, designer, and friend. This multifaceted, multi-passionate lifestyle has given you a unique understanding of the daily challenges people face and the solutions that genuinely work. This holistic view of the lives of your clients will humanize them in a way few competitors will prioritize. Embrace this insight to better serve the lives of your clients.

14. Be intentional about buying back your time.

The greatest value that money can afford you is the ability to buy back your most underrated asset – time. I know it’s tempting to save money by doing everything yourself, but every hour spent on tasks someone else could handle is time stolen from the big-picture work only you can do. Strategic investments in outsourcing or automation might feel like a stretch at first, but trust me—they’re worth it. Protect your time fiercely; you simply can’t afford not to.

15. Sustainable growth is born from seasons of scrappiness and hustle.

The polished systems and workflows you dream of won’t appear overnight. They’re earned through the messy, resourceful early days of figuring it all out—pivoting, adapting, and doing whatever it takes. Those scrappy seasons teach you what works, what doesn’t, and how to build something solid for the long haul. Embrace the chaos required in the initial launch with the understanding that your systems will come when they need to!

16. Your success is shaped by the mindset of the 10 people closest to you.

The people in your inner circle influence your thoughts, energy, and perspective more than you realize. Surround yourself with individuals who inspire, challenge, and uplift you. Their belief in what’s possible will expand your own vision of success.

17. You won’t be the right fit for every client—and that’s okay.

Not every client will align with your approach, and that’s a good thing. When you focus on serving the right clients—the ones who value your work and are a true match for your expertise—you’ll create better results and enjoy the process so much more.

18. Your husband won’t resent your success—he’ll celebrate it.

You might worry that outpacing your partner’s success could create tension, but that fear is unfounded. He’s your biggest cheerleader, and your wins are his wins. Your growth is something you’re building together, and he’s proud of everything you’re accomplishing.

19. Fear of success can be just as paralyzing as fear of failure.

It’s easy to recognize the fear of falling short, but fear of what happens if you succeed can be just as intimidating. What will change? What will be expected of you? Recognize that fear for what it is, and remind yourself that you’re capable of growing into your next chapter.

20. Focused quality will always outshine breadth and speed.

Good news! Your clients aren’t picking you because you’re the fastest designer. In fact, many clients will come to you because they went to the fastest or cheapest designer first and received less than stellar results. Whether it’s the services you offer or the relationships you build, trust your instincts and keep focusing on delivering exceptional quality. Depth and intention will always leave a lasting impression.

21. You can’t achieve success until you define success.

For you, success has always been about creating a holistic and healthy lifestyle for your family—not just chasing growth for growth’s sake. While others may prioritize scalability or prestige, stay true to your vision. Your business is a tool to serve your life, not the other way around. Don’t let anyone else’s definition of success pull you away from what truly matters.

22. Choose abundance over fear—create space for big ideas to thrive.

A scarcity mindset keeps you trapped in fear, clinging to what you have instead of reaching for what’s possible. Abundance, on the other hand, creates room for creativity, innovation, and bold decisions. Embrace a mindset that focuses on opportunities rather than limitations, while staying grounded and responsible. It’s in that balance that true growth happens.

23. Don’t let scaling diminish your commitment to serving well.

Some advice will tell you to give 80% effort so you can focus on growth and scalability, but that approach comes at a cost—your clients’ experience. Your aspirations should never outpace your ability to deliver excellence. Growth is important, but not at the expense of the trust and value you’ve worked so hard to build. True success lies in balancing ambition with a steadfast commitment to serving others with your best.

24. Rest is the only cure for creative burnout – there’s no shortcut.

When your creativity feels drained, there’s no shortcut to getting it back—rest is the answer. It’s not a lack of discipline. It could be a lack of sleep, lack of encouragement, a hard conversation, a recent life change – it’s all connected, and the only way to recover is to give yourself the space to do just that. 

25. Entrepreneurship is full of distractions—stay focused.

The entrepreneurial world can feel like a whirlwind, with shiny opportunities and big promises pulling you in every direction. It’s easy to get caught up chasing what looks exciting or trying to match someone else’s goals. But remember why you started and what you’re working toward. Stay rooted in your own vision, and don’t let the noise—or anyone else’s aspirations—derail you. Your path is yours for a reason.

26. Don’t confuse brand recognition, sales revenue, or follower count with profitability.

It’s easy to get caught up in flashy metrics, but they don’t always tell the whole story. A well-known brand or impressive sales numbers mean nothing if your expenses outweigh your earnings. Keep your focus on building a business that’s genuinely profitable, not just popular.

27. Boundaries and clarity are the ultimate gifts for your clients.

Setting clear expectations and maintaining healthy boundaries isn’t just for your benefit—it’s how you serve your clients best. When they know exactly what to expect, they feel supported and respected. Boundaries aren’t barriers; they’re a framework for trust and success.

28. Your friendships will evolve, and that’s okay.

As you grow, so will the dynamics in your relationships. Some friends will cheer you on, while others may struggle to relate. It’s part of the process. Surround yourself with people who support your journey, even if it means letting go of those who no longer align with where you’re headed.

29. A salary isn’t as secure as you were raised to believe.

You grew up hearing that a steady paycheck was the safest path, but times have changed. Job security isn’t guaranteed, even in traditional careers. Entrepreneurship may feel risky, but it offers you something a salary doesn’t—control over your future.

30. You won’t survive this lifestyle without prioritizing your health and mindset.

Building a business is demanding, and burnout is real. If you don’t take care of your physical and mental well-being, it’ll catch up with you. Rest, move your body, and invest in your mindset. Your success depends on your ability to show up as your best self.

31. Make a CPA your first hire—you can’t afford not to.

I know what you’re thinking: “I can’t afford a CPA.” But here’s the truth—you can’t afford not to. A good CPA will save you money in ways you didn’t even know were possible, from finding tax deductions to avoiding costly mistakes. They’ll also free up your time and energy to focus on growing your business. Investing in professional financial guidance early will pay off more than you realize.

32. Talk about your business unapologetically.

Don’t hold back for fear of sounding salesy. Sharing your work isn’t shameless self-promotion; it’s letting the world know how you can help. The people who need what you offer can’t find you if you stay silent, so speak confidently about your business and the value you bring.

33. Quarterly breaks are essential for more than just rest.

Taking time away from your business doesn’t just prevent burnout—it gives you perspective, strengthens relationships, and lets you test whether your workflows can function without you. These breaks are as much about recharging as they are about ensuring your business is truly sustainable.

34. You weren’t dreaming too big—you were dreaming too small.

Those big dreams you once doubted? They weren’t the problem. The real issue was thinking they were the ceiling. Dream bigger. Your potential is far greater than you realize, so don’t hold back from imagining what’s truly possible.

35. You deserve every bit of your success—it wasn’t luck.

It’s easy to dismiss your wins as good fortune, but they’re not. You put in the work, took the risks, and stayed committed even when it was hard. You earned this, and you deserve to celebrate it without hesitation.

36. Position yourself well, and trust the right opportunities will come to you.

You don’t need to obsess over every lead or chase opportunities out of fear they won’t come again. You’ve done the work to build something intentional and aligned with the clients you’re meant to serve. The foundation you’ve created will attract the right opportunities. If it’s meant for you, it will find its way to you—no need to force it.

As I look back on these 36 lessons, I’m reminded that the journey of entrepreneurship—and life—is never truly linear. It’s filled with unexpected detours, valuable mistakes, and moments of clarity that change everything. These insights have served me well, and I hope they serve as a reminder to trust yourself, lean into the hard seasons, and stay true to the vision that matters most to you. If I’ve learned anything, it’s that success isn’t just about achieving goals; it’s about growing into the person you’re meant to become along the way. So here’s to dreaming bigger, taking bold steps, and always choosing the life you truly want.