Introduction: The Unexpected Darkness After the Exit
When I exited my business after 12 years, I imagined it would be the pinnacle of my career. At 38, I was free from the relentless daily grind and thought I would feel a deep sense of fulfillment—even joy. But instead of the liberation I anticipated, I sank into a deep depression.
My business had been my everything—a source of purpose, a reason to wake up each morning. It wasn’t just a job; it was a world I’d built and lived in every day. Without it, I felt utterly lost. I was isolated, unsure of what to do with my time. I had no new business ideas; it was as if the universe had shut the door on my creativity.
During my life after selling a business, I found myself in a funk, constantly comparing myself to other entrepreneurs who seemed to be thriving. I missed the routine, the structure, the focus—even the misery—it had been my purgatory. This mindset wasn’t just affecting me; it was impacting my family and our well-being. The only solace I found was in the gym and running daily to blow off steam. It softened the blows I was feeling.
But this dark period taught me a lot. Here are the lessons I learned that pulled me from the brink and set me on a path to redemption.
Recognizing When to Let Go of Your Business
I realized I had stayed in the business too long. I trapped myself in a situation that no longer aligned with who I had become. The company I built in my 20s was dragging me down by my 30s. There was a disconnect between the business I once loved and the person I had grown into. I struggled to find ways to help my team grow with me.
Looking back, I see that I ignored the signs. I should have stepped back sooner. My gut was telling me to let go, but I didn’t listen. I feared the unknown, losing my identity, and failing. But holding on can be more damaging than letting go. It’s like holding onto a rope that’s burning your hands—the longer you hold, the deeper the burns.
Recognize when it’s time to move on. Don’t trap yourself in a situation that no longer serves you. Trust your instincts; they often reveal what your mind refuses to see.
Pro Tip: Regularly assess your alignment with your business. If the passion fades and you’re not evolving with it, consider other opportunities.
Avoiding the Trap of Misplaced Happiness
I placed too much of my happiness and fulfillment in my business. When I walked away, I felt like I had nothing, even though I had everything I needed—a beautiful family, a nice home, wealth, and good health. I lost sight of the joy and love in my life outside of work.
It’s easy to tie your self-worth to business success. Our culture glorifies the hustle, the endless drive to achieve. But when that’s gone, what’s left? For me, it felt like an empty void.
Real happiness comes from balance—embracing both work and personal life. I had to reframe my thinking and focus on the joy surrounding me. My family, my health, my passions outside of work—these were the true treasures I had been overlooking.
Think of happiness like a balanced diet. If you consume only one thing, no matter how nourishing, you’ll end up malnourished. You need a variety of experiences to feel fulfilled.
Pro Tip: Take time each day to practice gratitude. Focus on what you have, not what you lack. This simple shift can change your entire perspective.
Embracing Vulnerability: Strength in Life After Selling a Business
I tried to be Superman, hiding that I was just another wounded soul. I believed showing vulnerability was a sign of weakness, especially in the business world. But I’ve learned that vulnerability is essential for success. It allows us to connect with others on a deeper level, to show that we’re human.
During my darkest days, I reached out to a mentor and opened up about my struggles. To my surprise, he didn’t judge me. Instead, he shared his own experiences with depression and burnout. That conversation was a turning point for me. It showed me that vulnerability isn’t a weakness; it’s a strength.
Think of vulnerability like the foundation of a bridge. It’s not visible, but it supports the entire structure. Without it, everything crumbles.
"Vulnerability is the birthplace of innovation, creativity, and change." — Brené Brown
Pro Tip: Don’t be afraid to be vulnerable. Share your struggles with trusted friends, family, or mentors. You’ll find that it strengthens your relationships and helps you grow.
The Freedom Found in Letting Go
I had to let go of the past to make room for the future. One morning, I cast my business into the ocean, metaphorically speaking. I threw it away like a cancerous tumor I needed to remove from my life. Only then could I move on.
Holding onto the past kept me stuck. It was like dragging a heavy anchor while trying to swim to shore. To find true freedom, I needed to cut that anchor loose.
Imagine a backpack filled with rocks, each one a regret or missed opportunity. As you let go of each rock, the load lightens, and the journey becomes easier.
Pro Tip: Create a ritual for letting go. Whether it’s writing down what you’re releasing on a piece of paper and burning it or saying a prayer of release, find a way to symbolically let go of what no longer serves you.
Aligning Values with Your Business Partners
One of the most eye-opening lessons was realizing that my values and aspirations didn’t align with our investors. The day they took over, the end was already written. There’s more to a successful business than just founder fit and product-market fit; there’s also investor fit.
I learned the hard way. If your values don’t align with your investors, no amount of success will feel satisfying. It’s like rowing a boat with someone paddling in the opposite direction. You’re not going anywhere fast.
When choosing investors or partners, ensure your values align. It’s not just about the money; it’s about the journey and the shared vision.
Pro Tip: Think of investors as long-term partners. Before signing any deals, have deep, honest conversations about values, vision, and long-term goals. Trust your gut—if it doesn’t feel right, walk away.
Balancing Work and Personal Life in Partnerships
Having my wife of 24 years in the business was a double-edged sword. While we complemented each other well, it also took a toll on our relationship. Every moment together became about work, and we lost the passion that had once defined our relationship.
We had to learn to separate business from personal life. We needed to find time for ourselves, away from the business, to reconnect as partners, not just as co-founders.
Think of a relationship like a garden. If all you do is tend to the weeds of business, the flowers of your personal life won’t bloom. You need to water both.
Pro Tip: Set clear boundaries between work and personal time. Schedule date nights, take vacations together, and find ways to reconnect outside of the business.
Steps to Redemption: How I Overcame These Challenges
My journey from depression to redemption wasn’t a straight path. It took time, reflection, and a lot of inner work. Here’s what helped me turn things around:
Set Limits: I learned to set clear expectations and limits within my business. Knowing when enough is enough is crucial. Don’t ignore your gut feelings; they’re often right. Ask yourself if what you’re sacrificing is worth it.
Surround Yourself with the Right People: Build a business that allows you to be around people who share your values. Hire the right team with clear job roles and invest in their growth. Your business should reflect your values and your vision.
Practice Gratitude and Presence: Be grateful for what you have and cherish every moment. Don’t spend all your time focused on the future. Appreciate the progress you’ve made and the beauty of where you are now. This simple practice helped me shift my mindset and find joy in the present.
Be Honest and Reflective: Take regular breaks to reflect on your journey and whether you’re still excited about your mission. Many founders are burnt out but afraid to admit it. It’s okay to change direction if it leads you closer to your true calling.
Choose Your Partners Wisely: Think of investors as long-term partners. Ensure your values align. If it doesn’t feel right, trust your gut and seek advice from mentors and peers. A misaligned partnership can derail even the most successful business.
Separate Business from Personal Life: If you’re in business with your partner, consider stepping back to preserve your relationship. Reassess your shared goals, wants, and values to keep the passion alive.
Conclusion: Moving Forward with Purpose
Sometimes, letting go is the only way to move forward. Your past doesn’t define you, and your business isn’t your identity. Embrace vulnerability, cherish what you have, and keep moving toward your true purpose.
The journey from depression to redemption taught me more than any business ever could. It taught me to trust myself, value the people around me, and never lose sight of what truly matters.
If you’ve ever felt lost after a significant change or are struggling to move on, I’d love to hear your story.
Share your thoughts in the comments below or email me at joe@joefenten.com.
Let’s connect and support each other on this journey of growth and self-discovery.
Your best days are still ahead. Keep pushing forward.
Further Reading:
For those who want to dive deeper into some of the concepts discussed in this post, here are a few books I recommend:
“The Power of Vulnerability” by Brené Brown: A deep dive into how vulnerability and openness can lead to personal growth and stronger connections.
“Letting Go: The Pathway of Surrender” by David R. Hawkins: A guide on how to release negativity and find true freedom.
“Option B: Facing Adversity, Building Resilience, and Finding Joy” by Sheryl Sandberg and Adam Grant: Offers strategies for dealing with setbacks and building resilience after life-changing events.
