Post-Exit Success: Do We Still Need the Chip on Our Shoulder?

Feb 22

Let’s be honest - most of us didn’t build our success from a place of peace and calm. We built it from a chip on our shoulder.

That chip usually comes from a deep-rooted feeling of not being enough; not worthy of love. Maybe it started in childhood - being left out, ignored, or growing up with less than those around us.

That discomfort lit a fire under us. It pushed us to build, to win, to prove something.

And society loves it. Hustle, grind, succeed. It leads us to believe that if we just get rich enough, successful enough, we’ll finally be enough. The chip will magically disappear.

But here’s the problem: it doesn’t.

Even after we “make it,” the same insecurities stick around. The inner battles don’t stop just because we’ve crossed some arbitrary finish line.

The satisfaction, the emotional safety we thought money would buy? Still out of reach.

The Hidden Cost of That Chip

This is where things get tricky.

After we’ve achieved worldly success, that chip - the very thing that drove us to succeed - starts sabotaging us.

Unresolved childhood trauma doesn’t vanish with financial success. It shows up in strained relationships, burnout, depression, and serious health issues. Sometimes, it gets worse post-exit, fueled by disappointment and confusion when success doesn’t fix what we thought it would.

We get stuck in loops of self-doubt and anxiety, unable to quiet the noise in our heads or feel good about what we’ve achieved.

At the same time, our entrepreneurial nature doesn’t disappear. The curiosity, the creativity, the restlessness - they’re still there.

We feel like we can and should do more, achieve more, give more, live more.

That leaves us with a real question: Do I need the chip to keep building and achieving? Or do I let it go and risk losing the fire that fueled my success?

This dilemma can paralyze us for years - or worse, push us in the wrong direction.

The Two Common Paths (And Why Neither Really Works)

After 13 years of studying founders post-exit, I keep seeing the same two patterns.

First, some of us cling to the chip.

We stay hungry, competitive, relentless. The thinking goes, “I need this chip to keep achieving - it’s just the price I have to pay.”

And it works - until it doesn’t.

Over time, fueling success with old insecurities drains us. Energy drops, decision-making slips, and stress starts to take over.

Stepping back feels like quitting, but pushing forward feels like burning out. Regret and a lingering sense of unfinished business creep in.

Eventually, the fire that once drove us turns into resentment.

Others go all-in on healing.

Therapy and retreats offer quick relief, but they rarely solve the dilemma in the long run.

Post-success psychology is poorly understood, and the unique mix of wealth and the loss of entrepreneurial purpose is something you can’t fully grasp until you’ve lived through it. Finding someone who truly relates to our experience - and can actually help - is rare. Besides, spending endless hours reliving past traumas and venting often clashes with our future-focused, problem-solving, entrepreneurial DNA.

Many of us end up retiring early or shift into low-stakes activities like investing or advising.

At first, the pressure lifts. But over time, the fire dims.

Life becomes too comfortable, and the energy and drive that once defined us fade.

We’re left with a quiet - but empty - sense of being done too soon.

Is There a Better Way?

Yes! I’ve certainly seen impressive examples of exited founders building fulfillment while going on to achieve even greater entrepreneurial success. But it requires a different framework and specific actions.

These founders neither cling to the chip, nor retire, nor obsess over therapy.

Instead, they internalize four key ideas:

1. Safety first

There’s a popular myth in founder circles that safety equals complacency - and that it kills our drive. I’ve found the opposite to be true.

When we create real safety - emotional, physical, financial, and social - we stop wasting energy on stressing over our fears and insecurities.

That freed-up energy fuels creativity, ambition, and the desire to build. We build not because we’re scared to stop, but because we genuinely want to.

Safety isn’t just about resolving past trauma.

While improving self-knowledge is essential, safety also requires holistic external action: securing close relationships, protecting wealth, and establishing habits that reduce stress and sustainably support our physical and mental well-being. Basic practices like regular exercise, meditation, and gratitude are part of this process - along with cultivating an abundance mindset and building foundational investment knowledge.

Only once we’ve built a solid foundation of safety should we move on to seek our next big thing - something that gives our life meaning and purpose.

2. Purpose dissolves fear

When I talk to someone who’s been in a conscious pursuit of purpose for years, I rarely detect any trace of a chip on their shoulder.

Why?

Because purpose makes insecurities small in comparison - it shrinks them into oblivion.

It becomes something we care about so deeply that we’re willing to push through fear and doubt without hesitation. The more we do it, the easier it gets - until, over time, our fears and insecurities dissolve altogether.

Purpose pulls us forward with irresistible power and self-sustaining energy.

No pushing. No hardship. No need for that chip on our shoulder.

3. The right tribe heals

We’re social creatures. Success after the exit requires being around people who have built their own safety and are living with purpose.

The right circle supports our evolution better than our own sole ambition ever could. We need people who believe in us more than we believe in ourselves at times. A strong tribe makes safety and purpose tangible, sharpening our focus and expanding what we think we’re capable of.

Carefully upgrading our social circle post-exit makes the difference between knowing what to do and actually doing it. It helps turn insight into action.

And purposeful action, when it comes from a place of safety, heals better than therapy ever could.

4. We must build our very own post-exit toolbox

A mindset shift is critical, but it won’t take us far without mastering the specific skills that sustain our post-exit transition - skills that create safety, deepen purpose, and help us build a stronger, more aligned social circle.

Managing our emotions, cognitive biases, energy and wealth, building a new structure, and cultivating non-transactional relationships are just some of the essential tools for transitioning from worldly success to deep fulfillment.

A new life demands a new toolbox - one that’s our own.

The Bottom Line

We don’t need to carry that chip forever. It got us here, but it won’t take us further.

Instead, we need to: