“Why abandon a business that's already thriving?”
This is exactly the question I asked myself when I started to challenge the comfort zone I'd built.
A productized data service business averaging $90,000 per project, a 90% closing rate, and enough freedom to spend half the year traveling. Why change what seems perfect?
Why should you care about this story?
As a data leader, data freelancer or aspiring data freelancer you may be facing or will be facing a similar crossroads.
Perhaps you currently have a stable data freelance business and are enjoying good money and flexibility. But deep down, you're wondering if your current situation is sustainable long-term or if you could achieve even more freedom, fun, and money.
Or maybe you're a data leader contemplating leaving the comfort of your job to launch your freelance career, uncertain if you should risk stability for more autonomy.
👉 Can your freelance business weather future market shifts?
👉 Could you boost your freedom and income even higher?
👉 Is there a more future-proof and fulfilling path you haven’t explored yet?
👉 Should you stick with what you know or venture into new territory?
Everything that's happening in AI is certainly stirring things up and it definitely triggered me to ask some hard questions about my life and work setup.
My own journey, with all its ups and downs, hopefully offers real-world insights and practical lessons to help you make informed decisions as you navigate these pivotal choices.
The golden cage of my existing core business
I built a successful business designing, building and operating data infrastructure specifically for consumer scaleups funded by venture capital and private equity. A few years back, I moved from hourly freelancing to offering a standardized, highly efficient productized service.
What worked well for me?
- A hyper-specific ideal customer profile was the cornerstone of my success and the reason for my high closing rate of about 90%
- I designed my productized service in a modular fashion with low entry barriers. This also helped with the high closing rate.
- I also designed it for long project duration because I didn't only build the data foundations, I also carried them into the organization as a fractional head of data
- A strong reputation built around one very specific use case and long project duration with 0 churn meant that my pipeline was always full
- Reusable frameworks, blueprints, and a reliable network for outsourcing meant that I can build and operate the setup hyper-efficiently (I ran data functions of 200 people scaleups solo with 1.5 days per week).
How would I rate this business?
- Fun: 8/10 (I love hands-on work and really enjoyed systematizing my data setups. Even though I outsourced a great deal of the work, I still wrote 80% of the code myself.)
- Freedom: 6/10 (Usually towards the end of my projects the fractional leadership retainer becomes a bit less free, even though I'm not bothered with people management or admin tasks. But at maximum 2 clients at the same time = max 3 days per week still pretty good)
- Money: 7/10 (At an average of $90k project size and the ability to do 4 of these per year with 3 days work per week, money was always pretty good. Not “I’m buying a new lambo every month kinda good” but still enough to travel 6 months every year, only fly business class on long-haul and stay in 5 star hotels.)
- Future-proofing: 4/10 (This was the weakest area due to lack of diversification, the risk of losing the fun running these projects and the risk of disruption from AI.)
The bottom line: While the business was profitable, enjoyable, and afforded a good lifestyle, I realized its long-term viability is questionable.
Challenging the comfort zone: A bumpy ride
About one and a half years ago, I decided to diversify. I asked myself:
👉 How can I boost fun and freedom even higher?
👉 How can I make my business more future-proof?
👉 Can I achieve at least the same financial success with more scalability and less dependency on only one business model?
I started exploring multiple ventures:
My honest assessment: The ups and downs
Switching from something secure to something experimental isn't easy. Here's how my situation changed:
Current ratings:
- Fun: 7/10 (Right now, I'm having slightly less fun than working exclusively on my productized service. I realized that fun is more volatile compared to running my productized service, with many 10/10 days but also a few 3/10 days)
- Freedom: 4/10 (Right now, I'm working MUCH more than before, with less free time for traveling and hanging out with friends.)
- Money: 5/10 (Income is certainly down compared to running my productized service and I'm prepared for it to stay like this for a couple of months. Solopreneurship is a loooong game!)
- Future-proofing: 7/10 (Sometimes I feel so dumb to abandon such a well-working business but I feel like I'm clearly better positioned for the long run and it's just a matter of time until money and fun reach the same levels as before and Freedom reaches higher levels.)
Key insight: Transitioning to new business models involves sacrifices: financially, emotionally, and time-wise. Patience, resilience, and long-term thinking become crucial (and sometimes they can mess with you pretty hard. I will be honest with you: I had multiple days where I thought "F**k it, I'll just go back to my previous life.")
The silver lining: lessons learned and actionable advice
Throughout this journey, several critical lessons emerged that I want to share clearly with you:
➜ Always question stability:
Stability today doesn’t guarantee security tomorrow. Diversifying or reinventing your offering regularly is crucial.
➜ Consider your personal rating system:
Consistently assess your business through these four lenses:
- Fun: How much enjoyment do you derive?
- Freedom: How much control and flexibility do you have?
- Money: Is your income sufficient for your desired lifestyle?
- Future-proof: How sustainable is your business model long-term?
➜ Accept temporary setbacks:
Understand that short-term sacrifices in freedom and money can lead to long-term stability and better opportunities.
➜ Create clear boundaries and guidelines:
When starting new ventures, set clear parameters for success and failure. Regularly evaluate your progress objectively.
➜ Leverage existing strengths:
Don't disregard your proven frameworks, network, and domain knowledge. Use your past success as a platform to accelerate growth into new ventures.
Are you thinking about similar changes?
If you're contemplating diversifying your data business, productizing your services, or moving into mentorship, training, or building communities, consider these questions first:
- What exactly do you want to achieve? (More money? Freedom? Security?)
- How much are you willing to temporarily sacrifice?
- What is your clear plan B if your new venture takes longer than expected?
- How can you leverage your existing reputation and skills for new offerings?
Be brutally honest. Accept that experimentation is uncomfortable and involves uncertainty, but also understand that the long-term payoff can be substantial if navigated wisely.
The bottom line
Switching from something stable and good enough to something better can feel dumb, but it's brave. It's strategic. The key is to move thoughtfully, be patient, and constantly reassess your direction.
My journey isn’t finished, and perhaps yours is just beginning. But if you apply this honest reflection and structured approach, you can build a future that's both fulfilling and resilient - exactly what we, as ambitious data professionals, deserve.
Let’s keep learning, iterating, and growing together.
Until next time,
Sebastian
