Throughout history, people have come up with many ideas of what freedom is, and some have questioned whether freedom is even technically possible. Perhaps we are just automatons without free will. That is a potentially impossible question to answer, and I will bypass it in this article. Instead I want to build my argument on our ordinary experience of freedom. Whether that experience is real or merely perceived, we seem to have at least some ability to make choices, and so we perceive ourselves as having free will. That is the freedom this article is concerned with.

What optionality is

Optionality is essentially this: given a certain state of affairs, we have a certain number of options available to us. If you don’t have a passport, your travel is restricted. Having a passport offers optionality.

As far as I know, the term was really popularized by Nassim Taleb in his book Antifragile, where he traces how optionality was one of the essential ingredients of his own investment strategy, and then extrapolates it into a broader code: one should design one’s life around optionality.¹ Taleb adds a caveat that matters for everything that follows: an option only has value if you are willing to exercise it. Hoarding options you never use is not freedom, it is indecision with better branding.

I think this is a great idea. In fact, I think that thinking of freedom as simply having optionality available at a given moment is a good way, perhaps the best way, to think about it. But there have been other ways of considering freedom throughout history, and so I want to make a few quick side stops first.

Side stop one: freedom from debt

The oldest notion of freedom we can find is freedom from debt. In David Graeber’s book Debt there is a great exploration of the origins of debt and money, and it turns out that the word freedom has its roots in being free of debt. Quite literally: the earliest recorded word for “freedom” in any human language is the Sumerian ama(r)-gi, found on the Cone of Urukagina, a ruler of Lagash around 2350 BCE. It means “return to the mother,” and it described a royal decree that cancelled outstanding debts, returned land to its original owners and released debt-bondsmen to go home to their families. Freedom, in its first written form, meant a clean slate.²

Debt has been around for as long as we have written records, and is not, contrary to popular notion, a recent invention. Credit came before coins. And back then, debt was entangled with all sorts of suffering. If you were unable to pay off your debts, not just your resources or land could be confiscated, but your very family members, and in some cases your own freedom. The Code of Hammurabi stipulates that a man who cannot pay may hand over his wife, son or daughter to work off the debt for three years. Babylonian kings issued some thirty general debt cancellations between roughly 2400 and 1400 BCE, typically on taking the throne. The Hebrew Bible institutionalized the practice in the Jubilee, a fiftieth year in which debts were forgiven and bondsmen freed. In Athens, Solon’s seisachtheia, the “shaking off of burdens” of 594 BCE, abolished debt slavery outright after farmers had been losing land and family members to creditors.³

Graeber adds an echo in our own language: the English word “free” derives from a Germanic root meaning “friend,” because a slave, unable to make binding promises, could not have friends in the full sense. To be free was to be able to commit.

Side stop two: freedom from heavy taxation

A second notion of freedom is freedom from heavy taxation. Being Belgian, my favorite example comes from the Low Countries. In 1569 the Duke of Alba, governing on behalf of the Spanish crown, tried to impose a permanent ten percent sales tax on every transaction of movable goods, the “Tenth Penny,” on top of a one-off levy on capital and real estate. The provinces had always granted their taxes by consent, one request at a time; a permanent tax, decided in Brussels and collected without their say, was a different animal. When Alba tried to enforce it in 1571, merchants in Brussels shut their shops, towns refused to collect, and the Tenth Penny became one of the grievances that turned a simmering religious conflict into the Dutch Revolt. Alba withdrew it in 1572. The tax itself was never really collected; the fight was over who got to decide.⁴

Integral to that idea of freedom is the limitation of taxation, so that the individual keeps more of his prosperity to enjoy in his own pursuits.

Crude measures

It is easy to see why people associate freedom with their financial situation; both historic examples show it. But these are crude measures, since our notion of heavy taxation seems to depend heavily on where and when we live. Imagine a New Yorker of 1776, who paid no income tax at all and carried roughly a thirtieth of the tax burden of a Londoner, stepping into the New York of today and finding out that a successful Manhattanite can lose roughly half of every additional dollar earned, between federal, state and city taxes. We can only imagine the horror.⁵

Debt, too, has evolved, and perhaps one’s balance sheet is a better measure of freedom in that sense. But both of these, taxation and debt, are ultimately components of optionality.

Why optionality is the better measure

The reason I think it is better to think in terms of optionality is this: if we really sense that freedom has something to do with decisions, then optionality is the most direct measure of it. There are cases where someone has a lot of wealth, low taxes and no debt, and is still limited in optionality. Some of the most fiercely free people I have known have been poor. They have been extremely creative in how they handle life and, in equally resourceful ways, in how they find joy in it. One friend of mine is fond of making extraordinarily fun and creative drawings on plain printer paper with markers, and often when he has friends over, they join him and draw together. It is somehow not an activity I have spotted as often amongst my more affluent friends. Yet I regard this kind of creativity as a high measure of freedom, in the optionality sense.

Philosophers have a name for the distinction I am circling. Isaiah Berlin separated “negative liberty,” freedom from interference, which is what both of my side stops describe, from “positive liberty,” the real capacity to act. Amartya Sen went a step further and defined development itself as the expansion of people’s capabilities, the real freedoms to do and be what they have reason to value, arguing that income is only a crude proxy for them. Functional optionality is, more or less, Sen’s capabilities in a founder’s vocabulary.⁶

I am not, however, advocating for poverty. In fact, I think the single greatest reason to pursue wealth is to increase one’s optionality. The ability to go wherever, whenever one pleases is a great joy in life worth striving for. Money can buy health and experiences, and it can help extend our lives. All of these things increase optionality tremendously. This, I think, is the most important reason to pursue wealth.

Ironically, in the pursuit of wealth we have to recognize that optionality might, seemingly, be severely decreased. Personally, while I built my company DESelect, I worked very long days for many years, spending all my waking hours on the business. My “free time” would be spent quickly eating a meal or getting a workout in to stay healthy, which in many ways was still in service of the business. And I would, of course, work through the weekends as well. From the outside, it might seem that my optionality was reduced. But even at that time, my optionality increased in interesting ways. Doors opened that had not only been closed to me before; I simply hadn’t known they existed. People I had looked up to as a fledgling entrepreneur became mentors, sometimes even peers. Networks opened up.⁷ And then there were the more straightforward things, like being able to fly business class and enjoy the comfort whenever I took a plane for work.

Freedom in responsibility

This brings me to perhaps the most counterintuitive statement of this piece: there is freedom in responsibility. The reader, now understanding the importance I attach to optionality, can probably draw her own conclusions. Essentially, when people take up more responsibility, they may be limiting themselves in certain aspects. Someone who has a child is now committed to raising that child for approximately twenty years, will be more financially constrained, and will lose a lot of sleep, especially in the first few years. But at the same time, a whole world of optionality opens up through the joy of parenthood: the pride, the richness of emotional connection, and the quieter, more serious side of life that seems to come with parenthood as well.

History offers the same lesson at the scale of nations. The American colonists of the 1770s were, by the numbers, among the least taxed people in the Western world. What they rebelled against was not the size of the bill but the fact that they had no seat in the body that wrote it. “No taxation without representation” is not a demand for lower taxes; it is a demand to carry the responsibility of deciding them. Having won that responsibility, the new states promptly tripled their own tax burden to pay for the war. They had less money and were, by their own account, more free.

Viktor Frankl made the point more bluntly. Freedom, he wrote, is only half the story; the other half is responsibility, and he suggested that the Statue of Liberty on the East Coast be complemented by a Statue of Responsibility on the West Coast.⁸ Chess players know a version of it too: a pawn that is never moved has every square theoretically open, while a piece that commits to the centre is the one that controls the board. Commitment reduces hypothetical options and multiplies real ones.

From community service to running a business to taking an active role in politics, all of these come with great responsibilities. But in them we can find great power: the power of optionality.

So here is the question this whole piece circles, and I would love to hear your answer. When in your life did you feel most free? And, looking back, how many real options did you actually have at that moment?

Notes

1. Nassim Nicholas Taleb, Antifragile: Things That Gain from Disorder (2012), Book IV.

2. David Graeber, Debt: The First 5,000 Years (2011). On the Sumerian ama(r)-gi and the Cone of Urukagina, see also Michael Hudson, “Modern (Mis)interpretations of Clean Slates.”

3. Code of Hammurabi, §117. Leviticus 25 on the Jubilee. On Solon’s seisachtheia, Aristotle, Constitution of the Athenians, chapter 6.

4. On the Tenth Penny and the Dutch Revolt, see Geoffrey Parker, The Dutch Revolt (1977).

5. Colonial tax burdens: Alvin Rabushka, Taxation in Colonial America (Princeton, 2008); Gary Walton & James Shepherd, The Economic Rise of Early America (1979). New York 2026 rates: New York State Department of Taxation and Finance; the 10.9 percent state rate applies above $25 million, the 3.876 percent city rate well below that. Combined with the 37 percent federal top rate, a high earner in Manhattan faces a marginal rate of roughly 52 percent on each additional dollar. The average New Yorker pays far less; the comparison is about the top of the scale.

6. Isaiah Berlin, “Two Concepts of Liberty” (1958); Amartya Sen, Development as Freedom (1999).

7. Network access deserves its own essay. Who will take your call, who will make an introduction, who will tell you the truth about a deal: these are options too, and they compound.

8. Viktor Frankl, Man’s Search for Meaning, from the 1984 postscript “The Case for a Tragic Optimism.” A Statue of Responsibility has been proposed several times since; none has been built.

7 years ago, I co-founded DESelect, a B2B enterprise SaaS company in the Salesforce ecosystem. We built tools that helped enterprise teams better activate and segment their customer data — and for a long time, we grew fast. We raised venture capital, expanded internationally, served global brands, and navigated all the chaos that comes with scaling a startup.

In 2025, DESelect was acquired by Unaric for 8 figures. The company continues to live on inside a broader platform, and I’m still actively supporting that journey today.

This post isn’t about the acquisition mechanics or the highlight reel.

It’s about what the journey actually taught me — as a founder, a CEO, and a human being.

I’m sharing these 33 lessons not because I think I did everything right, but because I’ve benefited enormously from founders who were willing to be honest after the dust settled. This is my attempt to pay that forward — with a bit more nuance, humility, and context than an X thread ever allows.

“Experience is the best teacher”. That’s another way of saying “it’s hard to learn from others’ lessons”. Articles like these are often cursed with some level of abstraction, even vagueness. I have tried to balance privacy and confidentiality with concreteness and authenticity. May you see the lessons behind the words.

Here goes, in random order...

1. Hard work matters — but awareness matters more.

I’ve always believed success requires working hard, not just smart. And that belief carried me far. But I didn’t realize how often I was pushing myself beyond what was healthy, almost on autopilot. I equated effort with worth.

Example: In the early years, I worked every night and weekend. It got results, but it also dulled my sensitivity to when I was running on fumes. Later, when I took even a single week off, I came back sharper and more balanced — proof that rest amplifies output.

2. Naivety is natural, but unchecked speed magnifies it.

I moved fast because that’s what I thought founders were supposed to do. But I often didn’t know what I didn’t know — especially about hiring and what “great” actually looked like.

Example: Early hires who didn’t scale with the company cost both time and morale. I could have slowed down, sought more outside perspectives, and trusted my gut earlier when something felt off.

3. Fundraising brings validation and invisible pressure.

Our $5.5 million seed round was one of the proudest moments of my career — proof that others believed in what we were building. But with that came an unspoken contract: keep growing, keep delivering, never slow down. (In total, we would raise ~$7m.)

Example: Right after closing the round, I jumped straight into expansion plans (good), but also took on too many initiatives (not good). That urgency, more than anything, came from the pressure I put on myself and the feeling I had to meet certain expectations.

4. Listen to your gut — even when it’s inconvenient.

I’ve learned my intuition is almost always right. When I ignored it, it wasn’t because I didn’t feel it; it was because acting on it was uncomfortable. (And even when your intuition turns out to be wrong, it’s still a good idea to follow it. This way it can learn because, you too, are a “machine learning”.)

Example: There were moments when I knew someone wasn’t the right fit — but I rationalized hiring them because it was easier in the short term or they worked for an impressive company. Every time, it backfired later.

5. The power of empathy

Looking back, I acknowledge I lacked empathy throughout a good part of this journey—only toward the latter stages did my awareness around this gap grow. Empathy can focus both on others and myself. The good thing is that empathy is a skill that can be cultivated.

Example: I would sometimes brush off feedback from team members. But these were important signals that justified pausing and sitting with the feedback for a moment to feel it out.

6. People-first doesn’t mean person-dependent.

At times, the company adapted too much around individuals instead of staying anchored in what the organization truly needed. It made things more fragile. Better to ask yourself: “What should my org look like?—and then match people and their skills to the required roles.”

Example: A few times, I adjusted structures or timelines to accommodate specific people, thinking it showed care. But it often ended up with a skill gap for a given role.

7. Leadership isn’t about doing less — it’s about focusing better.

There were cases in which I micromanaged too much. There were cases where an employee perceived me to micromanage, when really they needed to be "managed to performance". But there were also times I stepped away too fast from things I should’ve held onto a bit more. True leadership is regularly taking a step back and deciding where you can actually move the needle most.

Example: There were a number of times I should have stayed closer to strategic product decisions, to make sure our offering was aligned with our ICP and buyer/user persona.

8. Burnout hides behind progress.

At some point, I didn’t notice burnout creeping in because things were still moving forward. I told myself exhaustion was temporary, that I could push through. But burnout doesn’t announce itself — it erodes gradually.

Example: I had periods of extreme stress masked by achievements: big deals closed, milestones hit. But I wasn’t sleeping well, and small problems felt enormous. Recognizing that pattern helped me step back earlier in the later stages.

9. Vacations are not indulgences — they’re investments.

Every time I disconnected, even briefly, my leadership improved. I saw patterns I’d missed, came back with energy, and handled people more patiently. (It's funny how, as a founder, even your vacations are in service of your career.)

Example: The difference between taking no break and taking one week off was enormous. I never took two weeks — but I now know that one longer reset each year would have paid for itself tenfold.

10. The CEO carries energy more than tasks.

What people pick up from the CEO is not just direction but tone. When I was calm, the team mirrored it. When I was rushed or stressed, that rippled too.

Example: During the M&A process (the last year of the journey), even though I was under intense pressure, I made a conscious effort to appear composed and give direct reports space. That steadiness made them more confident.

11. Resilience is built by surviving, not avoiding, pressure.

Especially during the year of the M&A, I surprised myself with how much I could hold together. That period tested every part of me — business, emotional, personal — and I realized endurance is a muscle you build through pain, not theory.

12. A company’s pace should match its understanding, not its ambition.

Sometimes we tried to accelerate before our systems, people, or market fit were ready. Ambition is good, but it needs to be balanced by the maturity of the operation.

Example: We hired ahead of our processes, believing future revenue would justify it. It didn’t, which led to some unfortunate scaling back later. Moving fast only works when the foundation can handle the speed.

13. Restoring balance requires intention, not luck.

It’s easy to tell yourself balance will come “after the next milestone.” But it never does on its own. Balance has to be designed into how you live and lead.

Example: I used to think balance would happen naturally once things stabilized. They never did. It was only when I consciously carved out time for reflection, nature, and coaching that equilibrium started to return.

14. Reflection converts pain into progress.

The hardest moments — layoffs, conflicts, personal lows — became my biggest teachers only when I paused to reflect on them. Without reflection, pain just stays pain.

Example: Writing this retrospective itself is proof of that. Taking time to revisit everything has helped me understand patterns I couldn’t see in real time.

15. The most important relationship is with myself.

Everything — the company, leadership, success — flows from the internal state. If I lose alignment with myself, everything else eventually follows.

Example: During the most stressful periods, journaling, solo camping trips, and quiet time became my anchors. They reminded me that leadership starts with self-regulation and ends with self-awareness.

16. Often I did too much

There were times I personally took care of certain activities (fixing reports, workflows) which was probably not the best use of the CEO’s time. It was because I felt I didn’t have the right people on board. I should have really hired the right expertise and then delegated, so I could focus on CEO tasks.

17. Own finance from day one.

Early on, I did something right — I sat down with our CFO for half a day and grilled him with questions to build a mutual understanding of our numbers. It also gave me a crash course in finance. However, my co-founder had enjoyed more formal education in accounting, and because of that we ended up with an unclear reporting structure for Finance, split across leadership functions. In hindsight, that ambiguity created friction.

Example: In hindsight, any missed closing or unclear report should have been a full stop. The solution is a strong CFO (even fractional) paired with an external accounting firm for continuity, accountability, and experience — especially one with SaaS expertise.

18. Keep learning from experienced people.

That early finance session was one of the smartest things I ever did. I could have replicated that approach with other senior people — sitting down for structured learning, asking targeted questions, and actively building my skill set through them. Instead, I often stayed in execution mode and missed out on free mentorship from the talented people around me.

Example: We had investors, advisors, and experienced executives who could have accelerated my growth if I had tapped (even) more into them.

19. Interns and juniors require structure.

We had early success with interns, which created a false sense of confidence. Later, when we were busier, we brought on too many junior people without the structure or oversight they needed. The result was more chaos than leverage.

Example: Some interns and new hires performed well only because I or others had time to guide them. When we lost that capacity, performance dropped sharply. The lesson: only bring in juniors when there’s a solid layer of experienced mentors above them — otherwise you’re building fragility, not depth.

20. Transparency is good — oversharing isn’t.

One of the things I did best was creating transparency around numbers and celebrating wins. People loved that openness. But at some point, I crossed a line — sharing too many financial details and metrics that most people couldn’t interpret. Instead of motivating, it confused.

Example: I shared deep budget reviews and performance dashboards with the whole Exec team. It led to unproductive debates. Transparency works when it creates alignment, not anxiety.

21. Keep financial decision-making tight.

Not every topic needs to be democratic. Budget discussions should involve a small circle — CEO, CFO, and sometimes co-founders or board members. Beyond that, you create inefficiency and blurred accountability.

Example: We once held broad discussions on headcount and budgets in leadership meetings. It slowed decisions and created tension. The better model: agree on high-level strategy with the team, but keep budget allocation at the very top.

22. Celebrate the people who grow with you.

Some of my proudest moments were seeing people like our (eventual) VP, CS and our first sales rep rise through the ranks. They grew tremendously and stayed loyal for years. Even though not everyone’s story ended well, many employees still look back on DESelect fondly.

Example: Our VP CS’s growth from early employee to key leader showed what happens when you combine trust, coaching, and autonomy. Supporting people like him was one of the most rewarding parts of the journey.

23. Impact matters more than perfection.

Despite a rollercoaster journey, the net result was positive for many. Employees often told me they learned a lot from me and enjoyed their experience.

Example: During a recent heartwarming Christmas drink where we invited ex-employees, I was touched by how many were deeply grateful for the opportunity and what they learned. Some said they never experienced a company culture that was so close-knit, either before or after DESelect.

24. Pain teaches what advice cannot.

I often read lessons from mentors or other founders, nodded in agreement, and still made the same mistakes. Only after feeling the consequences did the learning truly stick. Experience is the most painful but reliable teacher.

Example: You can hear over and over that hiring is hard and critical. But actually doing it is what will really instruct you.

(Side note: Once again, I hope reflecting on this text can help you avoid some of my mistakes. 🙏)

25. Take competitive threats seriously... and immediately.

We underestimated a key competitive shift and didn’t act fast enough. In hindsight, I should have pushed harder for earlier action.

Example: When we learned our industry would set a different course, we should have started building our next-generation product right away, even though we would still significantly grow with our current products.

26. Focus beats activity.

A startup can’t run more than a few true initiatives at once. After the seed round, I was replacing a marketing leader, onboarding a European sales lead, opening a U.S. office, and hiring another European leader — all simultaneously. It was too much.

Example: Had I delayed the U.S. launch or skipped that extra European hire, I could have focused properly on one or two priorities and achieved far better results. Never spread leadership attention thinner than one or two key initiatives (on top of your day-to-day ops).

27. Never sign long-term vendor contracts as a startup.

We made the rookie mistake of signing multi-year leases — for offices, water coolers, even software. When the company’s needs changed, these became expensive anchors.

Example: We once had a four-year office lease and multi-year software deals that outlived their usefulness. Flexibility is worth paying for. One-year contracts may cost more per month but save later.

28. Reflect more deeply when targets are missed.

I pushed hard for data, but sometimes we drowned in it. We built endless reports instead of focusing on interpretation and action.

Example: One leader spent weeks buried in dashboards without a clear direction. We should have shifted from report-building to insight-driven conversations with the exec team, turning analysis into concrete adjustments.

29. Measure ROI ruthlessly, especially in marketing.

We spread our marketing budget too thin — too many channels, too little focus. Events worked, but we were slow to take them beyond simple sponsorships toward something that could have been more special. Paid channels rarely produced results unless managed by experts.

Example: External agencies often outperformed internal experiments. In hindsight, we should have outsourced paid channels until they were proven, and hired earlier for key roles like events management and product marketing with deep industry understanding.

30. Know when to sell.

At some point, we realized we had achieved respectable growth and had been building an amazing portfolio of enterprise logos. This led to an almost full year of preparing for the actual sale: cleaning up accounting & financial reporting, auditing costs extra carefully, and collaborating with an investment banker on acquisition strategy.

My advice to any entrepreneur: Don’t be greedy. When you can sell (partially or fully) for a life-changing amount, do it.

31. Define what kind of product leader you need.

Not all product managers are alike. You must decide whether you want a visionary or an executor — ideally someone who can do both in a startup. We lacked clarity here, and it hurt our roadmap.

Example: At some point, the company needed someone who could translate vision into reality, not just manage tickets.

32. Match strategic moves with organizational readiness.

My move to the U.S. was bold and right in principle. It impressed investors and embodied commitment. But I misjudged the readiness of the Belgian office, which we were still scaling at the same time as well.

Example: The U.S. move paid off externally but created internal strain. I should have spread out various initiatives / key hires a bit more.

33. Clarity beats compromise in workplace policies.

For too long, we had an inconsistent hybrid setup — some people remote, others in-office — with no unified direction. It was a symptom of leadership not being aligned on talent vision.

Example: That lack of clarity created confusion and uneven expectations. Whether remote or office-first, what matters is alignment. Half-measures only create frustration.

Closing

Building DESelect was a masterclass in creation, endurance, and self-confrontation.

I'll continue to bring the same intensity as I continue to build — but with more space around it. More reflection. More calibration. More trust in discomfort as a signal.

The founder's journey didn’t end with the acquisition. I’m still supporting Unaric, still learning, and still writing.

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