In February 2026, I will officially celebrate 3 years of being my own boss, and it made me reflect on the journey. Oh boy — tons of learnings, but I’ll try to keep it short.
How it all started
Three years ago, in early 2023, I made New Year’s wishes and wrote down that I reaaaally wanted some change in my professional life. I had climbed the classical career ladder for the past 10 years and felt somewhat undervalued at my current workplace, tired of corporate politics. Funny enough, literally two days later, I got a notice of being laid off … and after a punch to my ego, I couldn’t have felt happier.
That’s how it all started.
I was ready for the next step, and the universe gave me a gentle kick to fast-track the process.
My first year
I remember my first month as a free radical very vividly. Naps that lasted until the afternoon, and the list of fiction I could dig into after working full speed for a couple of years in a scale-up. However, I also felt pressure to start building and delivering from day one. At the same time, I was still asking myself if my field — recruitment and talent acquisition — was still my thing.
It took at least 3 months until I was certain that this is what I wanted to pursue, and until I gained my first paying customer. Plus another three months to actually have enough work coming in to provide stability and confidence to realize that I’d landed on my feet.
Lesson no 1: The work you put in today will pay off much later. Don’t quit during the first six (or twelve) months. Choosing to play the long game keeps you sane.
Starting a business right at the bottom of the crisis
The tech industry was going through several waves of layoffs, and while staying positive and manifesting the best, the competition for winning a client was huge, as I was competing with well-established recruitment agencies with solid references and strong employer brands.
Despite the circumstances, I wasn’t willing to sell myself below market value, so I needed to play to other attributes. I spent hours reflecting on my value proposition and what made me special, even if the service I offered was pretty much the same as that of other companies in the field.
What I realised was that my unique selling point is “me”.
We operate in the people business, and we want to buy from people that we trust, like, and resonate with. I couldn’t ensure that everybody would like me, but I could definitely express my values, work ethic, and character, staying authentic to who I am.
That became my strongest asset because I realized that there’s only one Heleen in the world. As I started to value myself more and more, it reflected back as others around me started doing the same.
Lesson no 2: As a starting entrepreneur, it’s tempting to say “yes” to every opportunity — after all, you want to capture all the money in the market. But choosing clients and projects that truly resonate with you, and playing to your strengths, is how you build your own brand. Trying to suit everyone rarely serves you for long.
The biggest fear I had to overcome
Starting off, I remember speaking with my therapist and telling her that one thing I’m the most scared of is being without a team and building everything alone. I remember her gently smiling and saying,
“Maybe the only way is to go through the fear and find out what’s on the other side.”
She couldn’t have been more right, because I found out that the fear of loneliness was just an illusion. I started to receive a sense of belonging through my dance and yoga communities, other freelancers and entrepreneurs who walked a similar path, and also through my friends and family, to whom I had much more energy and time to give than previously.
Funny thing — people who were supposed to be my “competitors” turned out to be partners. I developed a network of other freelancers in my field with whom I could discuss any challenges, from acquiring new customers to sharing pricing models. Huge shoutout to Artyom Kobahidze, Christoph Wiederhold, and Samira Soltani (and many others, actually) for your integrity and willpower walking a similar path!
Finally, I also realized that the ways of collaborating with my customers can be much more meaningful than just delivering one project after another. I started off with an interim talent acquisition partnership with Milrem Robotics, and later with LHV and FYUL, where I was embedded into the existing team while still keeping my freedom and other projects running. I don’t know if it’s just luck or the good people I met along the way, but I felt truly valued and part of the team from day one in each of those companies. Huge thanks to Gristel Tali, Katrin Koha, and Veronika Linkuma for trusting in me!
Lesson no 3: Building solo doesn’t mean being alone. By leaning into communities — friends, family, fellow freelancers, and mentors — you can create your own support system while keeping your freedom.
Cool stuff, but let’s talk about money
Maybe it’s Estonians pessimistic nature as we tend to keep the encouraging words to ourselves to survive the cold winters, as I often encountered reactions such as:
“Oh, it must be hard to be a solopreneur, and not financially worth it considering the time and investment you need to put into it.”
I’m lucky to say that I totally disagree.
I finished my third year with a recurring monthly revenue of €7.5k. When I started, I set a goal to hit €10k monthly, so I’ve reached 75% of my initial goal. Honestly, I don’t know if that’s good or bad.
There are so many things I cannot put a price tag on: starting most of my mornings by reading a book in bed until 11, going to the gym in the middle of the day, taking two-hour-long walks with my dog, choosing my own pace, time, and rhythm to do things, and having the freedom to pack my bag anytime and take the first flight to work, borderless.
But most of all, having the freedom to choose with whom I work, and when needed, to say without regret, “Thank you, that’s not my energy right now.”
Don’t start if …
It might sound like a dream come true (and trust me, most days it is), but there are aspects worth considering if you plan to start a business on your own.
- You need to be okay without knowing what comes next. Most of the time, I have no idea how busy I’ll be one month from today. You need to be okay with the fluctuations: when there’s a lot of work to do, everything comes at once, and you may feel anxious about whether you can deliver at the pace and quality that meets your standards. On the other hand, there are months where there’s hardly any work at all. Can you switch your mindset to: “Yesss, it means vacation time then!” and trust the flow?
- Entrepreneurship is a spiritual journey. At times, there is no other safety net but just the belief in yourself. You make a plan, but things often roll out completely opposite. Are you ready to look into the mirror when things go wrong and sit with your sh*t to pass through uncomfortable times? Whether we like it or not, there are plenty of those moments.
What I’ve learned the most
Building something on your own is an awesome ride! If you feel even the slightest whisper telling you to go your way, just do it!
But … it will be a self-growth on steroids.
These three years have pushed me to break so many subconscious patterns and do real deep work on my beliefs around money, success, and relationships — the raw, ugly work I needed to do to reach the freedom I have now.
I’m grateful to all my clients who have had faith in me from the early days. Helping to achieve your mission, whether it’s saving penguins or building a platform for people to speak more confidently, has offered me so much joy. Your trust has meant a lot.
What’s next for me? I am not sure of the details yet, but one thing is certain – I’ll continue changing, building, and creating.
Happy 2026!
Long story short
Remember. There is only one You.
Shine bright and go do your thing! 💫
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