5 Lessons learned in 8 years as an Entrepreneur

Aug 18, 2022 | entrepreneur | 0 comments

This year I’m celebrating 8 years as an entrepreneur. It feels like a big milestone especially considering that I never planned to start a business. In honor of the occasion, I’ve put together a list of five important lessons I’ve taken away from this adventure of being my own boss. 

So, if I never meant to start a business – how did I find myself on this entrepreneurial journey? Well, it all started when I was searching for something I was as passionate about as my entrepreneur boyfriend was about his startup. Little did I know that it would lead me to become an entrepreneur myself!

I instantly knew what activity I would pursue  – I loved writing and I’d abandoned it while doing my master’s. I was living abroad in Madrid, Spain at the time and working as a therapist in a clinic. So it seemed like the perfect opportunity to launch a blog about everything related to international living and psychology.

Well…as it turns out if you’re blogging about mental health and living abroad and you are a therapist…people may just start messaging you to ask about your therapy services.

Fast forward ahead a few months and I found myself opening a business in Madrid so I could start my private therapy practice for people living abroad. I still wasn’t entirely convinced I wanted to be an entrepreneur, but I decided to give it a try. Within a few months, I had to create a waiting list for new clients. I was really lucky that things went so well right away. Most business owners don’t have that same luck and I think it helped me keep going when things did get tough later on down the road.

However, I can’t say it was all luck because looking back, I also know there are quite a few things I did right without even realizing it. One of those is that I approached my business with a playful and experimental attitude. This was relatively easy since I didn’t mean for it to be a business at first. (I also had another job at the time). But it’s an approach I continue to remind myself of when I feel like I find my perfectionist tendencies creeping up in my business. We’ll say that’s lesson 0 of the 5 lessons I’ve learned over the years. Below I’m sharing 5 more things I’ve discovered during the 8 years I’ve been on this entrepreneurial journey. 

1. If You Follow Your Passion, Doors Will Open For You…but They May Not Be The Ones You Imagined

If there’s one thing I’ve learned as an entrepreneur, it’s this – doors will open for you that you couldn’t predict when you first started. Since I never planned to start one business, you might not be surprised to hear I definitely didn’t plan to be running two separate businesses! But that’s what happened when I co-founded the Location Independent Therapists (LIT) Community in 2020 with Dr. Sonia Jaeger.

Sonia and I met in 2017 when I was starting my own leap into the world of online therapy. In 2018 we met in person for the first (and so far, only) time when we presented at the 7 in 7 Digital Nomad Conference in Medellin, Colombia. We’d already collaborated together on several projects – co-moderating the LIT Facebook group, and creating a peer supervision group, mastermind, book club, and coworking for other therapists. And we started wondering – if all of this had been so helpful for our business growth… maybe other therapists would benefit from having this support too?

The idea for the LIT Community was born!

After a great deal of planning behind the scenes, we launched the LIT Community in February 2020 as a place for mental health professionals to connect with colleagues from around the world for support, guidance, and encouragement as they start or grow their online businesses.

In the 2.5 years since then, we’ve grown to over 50 members from countries around the world who are living & working across borders, many in multiple languages. We’ve also launched a LIT directory to help people find a location independent therapist and a scholarship for therapists who aren’t able to pay the full rate.

The LIT Community is a place for us to inspire other therapists to think outside of the box about the life they want to live AND the difference they want to make in a way that supports their clients and also their own well-being. It’s a pretty cool mission to be a part of, even though it never was part of my plan. 

It reminds me of the quote I have hanging above my desk that I think all entrepreneurs should keep in mind as they’re running their business because sometimes we don’t fully understand how things fit together until looking backward – 

Life can only be understood backwards; but it must be lived forwards.

Soren Kierkegaard

2) Sometimes, Instead Of Searching For Your Niche, It Finds You

Before I became an entrepreneur, the majority of therapy clients I´d worked with were struggling with eating disorders. For over a decade I´d dedicated myself to working with these clients in a variety of different settings, both in the U.S. and Spain. In graduate school, I had also pursued opportunities to carry out research and work in clinical settings where I´d gain additional experience with this population. I assumed that going forward in my career, this would be the type of client I would continue to work with.

But when I launched my blog the people who reached out to me were living abroad and seeking an English speaking therapist to help them with a whole variety of mental health concerns. Yes, some of them had an eating disorder, but it wasn’t the majority of people who got in touch.

Suddenly – I had a whole new niche staring me in the face, and I decided I wanted to explore it! 

For the next 7 years I worked in various capacities (first as an offline therapist, then an offline therapist, and eventually a coach) supporting the globally mobile community. I had the opportunity to work with clients living around the world.

Eventually what I found was that most of the people who reached out to me wanted support with navigating the “Should I Stay or Go” dilemma – choosing whether they wanted to stay abroad or move back home. This was a niche that found me that I eventually decided I wasn’t passionate about. It made me think about one of my favorite quotes I read on a Starbucks cup years ago from American journalist Po Bronson–

¨Failure is hard, but success is far more dangerous. If you’re successful at the wrong thing, the mix of praise and money and opportunity can lock you in forever.”

I didn’t want to stay locked in this niche forever which is why I decided to sit down and think about what my new niche would be. The interesting thing was that I once again realized – my niche had found me. 

When I thought back to the clients I’d worked with over the years that really lit me up I realized how much I’d been passionate about supporting my clients who were business owners themselves – coaches, therapists, consultants, graphic designers, people working in tech startups, etc. They often came to me to work on something related to living abroad, but usually, we ended up working on things related to their business mindset as well.

For a while I let my own imposter syndrome stop me from declaring that this was my new niche. After all, wasn’t I just an “accidental entrepreneur?” But after doing some of my own mindset work (and working with both a branding strategist and a coach) it became clear that the desire to focus on this niche wasn’t going to go away and it was time to focus my coaching on providing mindset coaching to entrepreneurs.

It’s been an excellent choice – I love being able to use my background in psychology, and my own experience as a business owner to help other entrepreneurs stop doubting themselves or procrastinating, and to pursue a better work-life balance.

3) Supposed Roadblocks In Your Field May Actually Be Challenges That Can Be Overcome

When I completed my master’s and became licensed to work as a psychologist in Spain, I did so expecting that I would have my brick and mortar office and see clients living in Madrid, which is where I was living at the time.

However, when potential therapy clients started reaching out to me, I found that many of them were not based in Madrid. In fact, some of them weren’t even based in Spain! They were located elsewhere in the world, where they didn´t have access to an English speaking or American psychologist.

“Can we do online counseling?” they asked.

I was hesitant at first. This was back in 2014 way before the pandemic made online therapy so popular. Most of the therapists I spoke with thought online therapy wasn’t “real therapy.”

But there were these people in my email inbox, all alone in a foreign country and struggling, and requesting online therapy…how could I say no?

As it turned out, online therapy most definitely is REAL therapy & a couple of years later I even decided to make my therapy practice 100% online. On some days I would start seeing clients ending their day in Asia & Australia and finish seeing clients just starting their day in South America. I saw clients while they sat by their pool, in hotel rooms on work trips, in their car on their lunch break, and even while they hiked Spain’s Camino de Santiago!

While online therapy certainly comes with its challenges, I discovered that the benefits seemed to outweigh the costs for most people. It helps people to get the emotional support in situations where they may not have had access to it previously and it’s helped people connect to a therapist who may have been hesitant.

Although I’ve since transitioned from therapy to coaching, this path also opened the door for me to co-found the Location Independent Therapists (LIT) Community to help other therapists to grow their own portable private therapy practice.

Now people tell me I’m a pioneer in the field of international online therapy and therapists around the world reach out to me for guidance to set up their international private practice. Going against the grain and pursuing online therapy, even in the face of critiques from my peers, has helped to define my career in a way I would have never imagined.

4) You can do Anything, but you can’t do Everything

When I first started as an entrepreneur I was constantly falling victim to shiny object syndrome. Only I had absolutely no idea that this is what it was. I thought it was very “entrepreneurial” to come up with a creative idea and run with it. Over the years I’ve realized that being able to say “no” is actually a hallmark of successful entrepreneurs. 

The truth is it took me many years to learn this. And it’s something I still struggle to put into practice. I’m a visionary, multi-passionate, and a helping professional. That combination together means that I am constantly coming up with new and exciting ideas and in my heart, I’d love to help as many people as possible.

I also consider myself a “time optimist” which means that I tend to think I can do more than a given amount of time than I actually can. (Tracking my time with Toggl over the years has definitely helped this – the importance of time tracking is like lesson 4.1 here actually!) 

One thing that’s helped me immensely to let go of shiny object syndrome is to create an “idea vault” where I record all of these exciting ideas that come to me. Then I’ve created moments throughout the year (especially at the end of the month, quarter, and year) where I can revisit these ideas and decide which of them gets priority. 

Becoming a mom helped to drive home this idea that I can’t do it all even further. The hours I can work and the energy I have are truly finite now that there is a little human who needs my attention. Especially if I also want to reserve some of that time and energy for my own self-care. Becoming a mom has really helped me to clarify my priorities and be able to say “no” more easily. (This includes saying no to certain clients and saying no to undercharging!)

Then earlier this year while reading “Four Thousand Weeks: Time Management for Mortals,” by Oliver Burkeman I came across this idea that helped drive home the importance of saying no even more. He suggests that if you want to make space for what you REALLY want, you need to say no to things that you only want. From now on, if something is only something I want (and not something I REALLY want), it doesn’t make the cut. 

5) Being An Entrepreneur Is About Personal Development Just As Much, If Not More, As Professional Development

There’s an enormous amount to learn when you’re an entrepreneur. Someone recently told me that it’s like being on an emotional rollercoaster – on top of a skyscraper. Based on my own experience and that of my clients, I’d say that’s pretty accurate!

The learning curve at the start of the entrepreneurial journey is incredibly steep and mistakes are inevitable. If you’re like most people, you probably never learned that failure was a good thing, and suddenly you need to start failing and fast! There’s also constant room for improvement and it can be hard to not get overwhelmed by information overload and a never ending to-do list.

I’ve always known that self-care needed to be a priority, but it took on an entirely different meaning when I became my own boss. I not only had to learn ways to improve my business, but I had to learn ways to improve myself. This part of the entrepreneur lifestyle–having to take a hard look in the mirror and realize ways in which you’re getting in your own way of growing your business – is what stops many entrepreneurs from continuing on.

Thankfully, I had a fair amount of tools in my toolbox and where I was lacking I read books and attended trainings (mindfulness courses were a lifesaver!). While it’s easy to feel a lot of pressure to seize the day and hurry up because ¨you only live once,¨ the truth is that life is more like a marathon than a sprint. If you try to sprint the whole way through, you’re going to burn out. If you want to be a successful entrepreneur, you need to have patience and find strategies that will help you to stay strong throughout the race.

In order to succeed in my own business I’ve had to work on being patient, self-compassionate and flexible with my own learning process. And this has also allowed me to learn a wealth of important tools to be able to help clients who are struggling as entrepreneurs themselves.

I’ve also learned the importance of being the best boss I can to myself. One of the reasons I love being my own boss is that I don’t have to deal with some of the aggressive, unfair, and inflexible ways I’ve been treated by bosses in the past. I think a lot of entrepreneurs can relate to this. But what ends up happening is that if we don’t stop to think about it we can become the very boss that we were so excited to escape! This is one of the things I am constantly learning to do better and a theme that comes up a lot in my conversations with clients. 

So there you have it, my top 5 lessons learned over the past 8 years.

What have been some of your biggest learnings along this rollercoaster ride of being an entrepreneur? Leave me a comment below – I’d love to know!


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I’m an executive coach for entrepreneurs who want to make an impact without sacrificing their mental health or relationships along the way.

I'm also a former therapist, host of the Founders' Fears & Failures podcast, and co-founder of the Location Independent Therapists (LIT) Community.