The Biggest Post-Exit Mistake
My Post-Exit Mistakes
To date, I've exited four companies.
My first 9-figure exit 13 years ago felt great—for a few months.
But soon, my life spun out of control.
My marriage ended, litigations erupted, friendships faded, and financial losses piled up.
My life felt empty. Purposeless. Joyless.
My children and I were in distress, my vitality waned, and my health suffered.
I tried to reinvent myself with a new venture, but its eventual failure dealt a harsh blow to my self-esteem, triggering an imposter syndrome and leaving me more isolated than ever.
During this time, I faced an identity crisis, questioning my worth and place outside the familiar networks of employees, partners, and the founder community.
Attempts to regain my identity through angel investing and start-up mentoring resulted in more financial losses, wasted time, and disappointment.
The societal expectation that wealth equals happiness made it nearly impossible to share my real struggles, even with my closest friends, adding to my sense of isolation.
My efforts to find purpose through philanthropy also led nowhere, deepening my sense of futility.
With the responsibility of raising two little children on my shoulders, I felt an urgent need to figure things out, stabilize, and be the best possible parent for them.
So, I embarked on a 13-year-long quest for clarity, contentment, and purpose.
I looked everywhere—from ancient spiritual scriptures to modern psychology, philosophy, immersive courses, retreats, and peer organizations.
I searched for wisdom around the world, from Peruvian villages and Indian ashrams to Harvard University.
Each experience helped peel back layers of the unique post-exit crisis phenomenon.
Over time, I healed and rebuilt my life.
I found love again, remarried, and welcomed a third child.
I am now the happiest, most fulfilled, and driven I've ever been.
I feel inspired, energized, loved, and loving.
Knowing that I am finally on the path that is truly mine and intentionally chosen is highly motivating and increasingly rewarding.
Collective Post-Exit Wisdom
Early on after my first exit, I started to painstakingly collect stories of fellow exiteers hoping to learn from their experience.
I connected with hundreds of exited founders globally, many of whom shared reflections of regret and enlightenment years after their exits, opening up about their missteps, struggles, and insecurities.
By now, my treasured collection of post-exit stories is over 1,200 and counting.
These interactions helped me step out of my own story, challenge my conclusions and concepts, and greatly expand and deepen my understanding of the post-exit phenomenon.
They culminated in a rich collection of insights and frameworks born from the trials of our collective journeys.
Over time, these encounters evolved into a warm, understanding, supportive, and stimulating community, which made an enormous difference in my recovery.
Eventually, this experience led me to discover my purpose—helping my fellow exited founders avoid mistakes and build joyful, fulfilling, and meaningful lives.
This newfound purpose led me to launch a blog and a podcast, called Exit Paradox, where I share what we've collectively learned so far.
The Most Common Post-Exit Regrets
"If only I knew then what I know now!" is what most of us exclaim years after our exit.
Experienced exiteers—those who sold a decade or more ago—most commonly regret the following three things:
Underestimating the psychological effects of an exit and how long recovery takes: This results in being stuck for years in a miserable void, filled with confusion, depression, anxiety, and broken relationships.
Underestimating the emotional challenges of the transition from an entrepreneur to an investor: This results in common mistakes like investing too early or for the wrong reasons: such as in friends' businesses or out of vanity, overconfidence, loneliness or thirst for a shiny new identity.
Starting a new business expecting less stress and work: This often quickly leads to even more stress, mental and physical exhaustion and exit wealth melting.
There's nothing inherently wrong with investing or starting a new business if done at the right time, in the right state, and for the right reasons.
However, many of us undertake these endeavors at the wrong time—when we're still burnt out, confused, and overwhelmed by our recent exit.
Our judgment is clouded and the quality of our decisions is poor.
If the root cause of these regrets lies in making poor decisions, wouldn't it be prudent to prioritize improving the quality of our decisions above everything else?
But how do we actually do that?
The answer is both easy and complex.
The quality of our post-exit decisions improves dramatically if—first—we take time to heal and—then—do the introspective work required to achieve intellectual clarity and the emotional and physical state most supportive.
The problem is that our old habits, fears, and insecurities, combined with our brain's natural resistance to change and preference for the easiest solutions, push us to avoid this challenge.
Avoiding the introspective work is the root cause of practically all post-exit mistakes.
It is therefore the biggest mistake we can possibly make after selling our business.
Post-Exit Introspective Work
Post-exit introspective work involves searching for our own answers to questions like:
Have I achieved the happiness I expected from my exit?
What about freedom? Am I just free to act, or also free to think without unwanted influences?
Who am I and who do I want to become?
What do I actually want? What makes me happy? Why?
What is my new direction? Purpose? Why?
Who do I want to surround myself with?
What am I truly good at?
What is the meaning of wealth for me?
Without answering these questions in the most honest and deepest way, we remain confused and blindfolded.
The chances of making the right decisions about our new direction are minimal.
Instead, we keep doing the same thing expecting a different result, or we follow others and lose autonomy.
This results in chronic dissatisfaction, lack of motivation, and energy.
It is, therefore, the primary responsibility of an exited founder to create time and space for introspection as long as needed.
What steps does post-exit introspective work involve?
Create time, space and energy for the introspective work: rest, heal, and have fun and adventures. Give yourself permission to not know. Let go.
Channel your focus away from financial concerns by committing to a "no-decision zone." Delay all consequential decisions like starting a new business, litigations, divorce, and long-term commitments. Learn to say no to financial requests.
Be extremely careful about others' advice: Avoid following the advice of those who haven't experienced a life-changing exit or who had it less than 10 years ago as they would not have had time to properly process their own experience and learn.
Start building a supportive and stimulating tribe around you: Learn to be exceptionally discerning, yet compassionate and generous. Understand how others may influence you without your knowledge. Protect your autonomy.
Go deep: Process your life experience, challenge your core beliefs, values, and concepts to achieve clarity and conviction. Create your new dream, find direction, and design your lifestyle aligned with your deep understanding of yourself.
By taking these 5 initial steps, we aim to optimize for learning.
This, in turn, will help us later optimize our life for happiness, instead of just accumulating more wealth and empty fame.
The German philosopher Arthur Schopenhauer said it best:
"It is difficult to find happiness in oneself but it is impossible to find it anywhere else.”
By doing the hard introspective work, we not only avoid the most common mistakes but also set ourselves up for a happy, fulfilling, and purposeful next chapter of our life.
The many-million-dollar question, however, is HOW to actually do this in a reasonable manner and timeframe without having to spend a decade meditating on a mountaintop?
And this is exactly what I’ve created Exit Paradox for. Together, we can create our most extraordinary chapter yet!
