• Ms. Lee

Three of the Hardest Lessons Learned During the First 90 Days of Entrepreneurship

Today marks ninety days of being a business owner, but my entrepreneurship journey started much further back. Let’s talk a walk.

Not many people know this, but Hey Ms. Lee was not my first business. Back in 2017, I married into the military and found myself unemployed so I optimistically thought I could start my own business without any support and zero business background.

Since I came from a non-profit background, I thought it made sense to start a non-profit consulting business so I created “PHI.LEE Consulting.” During those eighteen months, I had one client (from a previous employer). There was no significance of “PHI,” I just liked the word. Also, the logo I designed kind of ended up looking like a butt.

I'm clearly not a designer

That’s when I learned that just because you built it, they will not come.

Attempt #2. I loved to travel and I was an excellent planner. So I launched Airplane Mode, my travel consulting business that started off as a blog. This time, I had a handful of clients and made some money, but there was one problem - I hated planning for other people.

That’s when I learned that just because I’m good at something, it doesn’t mean I should do it for a living.

Here are the top three reasons why those businesses failed:

1. I did not set myself up for success.

I didn’t have a support system or any system for that matter. I naively believed that I could figure it out on my own because that’s how I accomplished everything else up to that point. Not only was I too stingy to spend the money on a business coach or a course, but I was also too prideful and ashamed to ask for help.

2. My perfectionist constantly got in the way (read my full confessions here).

I was overthinking every move which resulted in barely taking any action. I was also scared to step beyond my network so I only worked with friends, family, and former co-workers. I didn’t market or network beyond that. I hoped that my network would refer me, but I made the grave mistake of not asking for the referral.

3. Being a great employee doesn’t automatically make you a great entrepreneur.

When you work in a company, there are people to give you feedback and reinforce what you’re doing. There are tools to measure your time and your rate. None of that exists in entrepreneurship, especially in the beginning. I was so used to achieving my goals quickly, and without any benchmarks for success, I was doomed to only see failure.


Fast forward to 2021 and I was ready to attempt entrepreneurship once more (third time is the charm, right?). This time I was ready: I hired a business coach who shared the same values, I signed up for digital conferences, and I was clear on my purpose. Without those supports in place, I don’t think I would have made it to ninety days because honestly, I was ready to give up on day forty-five.

But I did it! I made it through my first season of entrepreneurship. Looking back, here are the most valuable lessons I learned:

1. Creative hours don’t carry the same weight as non-creative hours.

Creating something from nothing takes a lot more energy and focus than a repetitive task. For example, reading a book takes much less time and energy than writing a book. After spending four hours on creating, I was exhausted. I was used to working ten hours straight without breaking a sweat so this was new to me. Getting used to the work flow was challenging. Partially because it felt like the work happened at random times, and partially because I felt guilty for working less than a ‘normal’ workday of eight hours. The reality is, creativity can't be measured by hours.

2. I'm a creative anomaly so things got a little weird.

I was listening to a business podcast episode where the guest talked about the importance of organized operations. The guest explained that most creatives aren’t comfortable or as familiar with operations and project management, but it’s something they have to learn to run a business. That’s when I realized that I was coming from the complete opposite direction; my strengths are in operations and project management, but I’m a noob when it comes to going with the creative flow.

At first this made me feel like an imposter. Do I belong in this space? But then I realized that this could be an opportunity: I could teach other creatives, especially Type A creatives like me, how to transition from that operations mindset to a creative one. There’s this misconception that either you’re creative or you’re not, which is completely untrue, but I had to unlearn that belief. One of the tools that helped me with that is "The Artist's Way" by Julia Cameron.

3. Nobody cares. So do what you want.

Nobody cares how passionate you are about your business. Nobody cares if you succeed or fail. Sometimes, nobody cares if you don’t do the thing that you said you were going to launch (unless they paid you). This is not meant to be harsh - this is meant to set you free.

Nothing is permanent so let yourself play around. You get to decide when to pivot, when to commit, and when to let something go. It’s OK to be small at first because you’re still figuring it out. Your business will start off as an infant; all it can do is eat, sleep, and shit. Don’t expect it to graduate from college in the first year. In the beginning, just showing up everyday is more than enough.


These are the lessons that I struggled with the most so I'm going to continue working on them during the next quarter. I shared my reflections so that other solopreneurs feel seen and aspiring entrepreneurs can get an idea of what it’s really like to start a business. It’s not all about pitching to VC investors, having a ton of followers, and curating a beautiful Instagram feed. It’s messy, confusing, and sometimes lonely. But it’s also thrilling, satisfying, and oh so fulfilling.

Bonus perk: going on vacation without having to request time off just hits different.

Overlooking Dubrovnik, Croatia

Share this post with someone who needs to hear this right now. Comment below with your lessons learned or what was most helpful about this post.

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