The Startup
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The Startup

4 Hard Lessons from 14 Years of Entrepreneurship

Meaningful, random reflections from an entrepreneur adamant about using personal growth to become a stronger business owner and overall human

Photo by Castner Photography

I turned a year older this week, so I am naturally pretty reflective right now.

This year of reflection has been different from past years, I feel like my wisdom actually has character to it now. I’ve acquired milestones and lessons that have taken the time to age and cure into meaningful reflections for others, rather than angry ramblings.

Rather than hold on to these reflections just for my benefit, here are some of those meaningful, random reflections, from the perspective of an entrepreneur who has been in it for 14+ years, and has been adamant about using personal growth as a tool to become a stronger business owner and overall human.

Ask your mentors what broke their hearts, not what made their wallets

My view on mentors has changed tremendously over the years.

When I was a newborn entrepreneur, I initially sought out mentors who could give me knowledge and network bumps — these are wonderful of course, but this isn’t what I’ve found to galvanize a business to go from struggling to thriving.

As I’ve aged and seen what kind of mentorship turns an entrepreneur from another fish in the sea to one that becomes untouchable — I’ve noticed that those entrepreneurs receive mentorship in the form of surviving mental warfare.

These entrepreneurs revere the seriousness of losing mental battles and how much it hurts their business’ bottom line. Mental battles can range from self-worth struggles, co-founder gripes, to understanding how to recover after a large fail or financial loss.

If you can find mentors to walk you through how to valiantly go to combat and recover from these battles, you will become unstoppable. It is the only true magic wand that exists for entrepreneurs.

Because here’s the truth — you can learn and train on how to become the best salesperson and business in the world, but if you don’t clean up your mental blocks and possess an awareness of your shortcomings, you’ll never gain the tools to actually execute on that knowledge.

All that money you spent learning new strategies and tactics will sit in a vault within your mind and never be activated.

When you get into the practice of telling yourself the truth, you don’t want to play by anyone else’s rules

One slightly inconvenient thing happened when I started doing a lot of internal work on myself to be better — I was no longer capable of feigning interest in things that weren’t truthful for me.

I had done so much work internally on what I liked and didn’t like, and what were real truths vs. inherited and ego-driven truths for me. The benefit of this breakthrough was that the gray area of indecision was no longer attractive or enticing for me — all of my decisions became an easy hell yes or a no.

This is inconvenient when you really want to put some serious cash into your savings account, but you can’t bite your tongue and sign on to that high-figure consulting project because you think the client is absolutely ridiculous. This is inconvenient when you stubbornly refuse to entertain just a few years of work you don’t love in order to hit a pipe dream you want within the next 5 years.

You get to a place where you don’t really know how to play by someone else’s rules and you only want to play by yours.

The upside of this is that you get to a place where you only work on things you love and pursue interests that ignite you.

The downside is that you struggle with the humility of delayed gratification. And when it comes to building a business or going after a marathon of a pipe dream, it’s all about delayed gratification for the first few years. You have to become a master of patience during this time and do a lot of things you don’t want to do.

This has forced me to be creative when I build something new, but I’d be lying if I didn’t mention that there have been moments of tension and downright destruction when I completely stopped working on things I didn’t like, out of intense loathing for doing work that wasn’t aligned for me.

There were times when this impatience turned out ok, but for the most part, I shot myself in the foot during many of those moments. Patience and sacrifice is a serious virtue that needs to be practiced, especially for the truth seekers with lofty goals.

Committing to entrepreneurship makes you unemployable

There was a moment in my entrepreneurial career when I fantasized about not having to call the shots all the time and could follow someone else’s agenda. I was in a post-burnout phase and was tired of leading and making decisions, and wanted a break. I wanted to work for someone else and function in a role where I could just complete the tasks given to me and leave my work at work.

I went on a job search that was largely unsuccessful because I was, for lack of a better word, unemployable. I was either too qualified or had dabbled in too many different job roles in order to be eligible for a super-specific position.

I wish someone had told me this when I ventured down the entrepreneurial path — that when you choose this path, you are married to it without an option for divorce (at least this was my experience).

You are totally in the clear if you dabble with starting a company for a year or two, but if you’re a decade in, you become a bit of an anomaly when job hunting for something that’s not a CEO or a startup founder role.

Thankfully, I ended up shaking myself out of my burnout and returned back to my entrepreneurial roots. It is my ultimate life’s calling and even though I don’t like it sometimes, my curiosity is bound to it for life.

If I, however, wanted to truly work for someone else for my remaining days, I think that this would’ve been a really difficult flip.

I wish someone had given me the advice to really think about how I viewed my career from a 10-year perspective rather than constantly going with the flow, not questioning my larger vision and desires during my back-to-back entrepreneurial pursuits.

Entrepreneurship doesn’t change you, it amplifies who you were all along

People say that money doesn’t change you, it just amplifies who you were all along.

Entrepreneurship has the same effect — it magnifies who you were all along, and whatever it magnifies, can’t be hidden. This has made making entrepreneur friends I like really easy because everyone wears their character and heart on their sleeve.

Entrepreneurship magnifies your character because the act of creation is ego destroying or provoking.

When you’re pushed to put your best creation out there in the world via your startup, your ego goes haywire. You may overcompensate on the chest-puffing out of insecurity, or go into an imposter syndrome spiral due to a lack of confidence. Through your actions, the more acute entrepreneurs can sense if your business is doing well or not.

I know this is true because every time I ask the more seasoned entrepreneurs what they think about specific entrepreneurs, there’s collective agreement on — how Brian has a photographer following him around to give the impression that he’s doing well, but he isn’t doing the nose-grinding work to execute his mission and we all know it, or how Amy is building something incredible behind the scenes and is going to blow it out of the water when she raises her seed round.

Those who seek titles but hate doing the actual work become seen as that entrepreneur that likes going to a lot of conferences, but doesn’t put their head down and do the work. Those who are co-dependent struggle to bring their business to life if they don’t have someone to confirm their next moves and lean on during the execution phases. Those who possess strong anxiety around decision-making find it hard to launch their business because they never blow past consecutive decisions with strong momentum.

Your personal holdups and blocks come to the forefront for public viewing when you’re an entrepreneur. And this isn’t to shame you, because everyone including myself has these holdups — this is to point out that if you have mental blocks, you’re not fooling other entrepreneurs if you think that no one sees your challenges but you.

It takes a co-dependent, insecure, (the list goes on and on) entrepreneur to recognize another entrepreneur from its camp — so what I’ve learned is you have two choices: either accept this reality, or take the initiative to overcome and master your blocks to become the best entrepreneur and human that you can be.

I love writing thoughtful, personal Friday morning emails called The Crux to help entrepreneurs like you turn their startup chase into a victory lap. Join here to get my best musings in your inbox.



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Sophia Sunwoo

Sophia Sunwoo


I create moneymaking brands with womxn entrepreneurs who refuse to settle for mediocre.