2018 was the year I lost the business, the marriage, and most of my confidence in one continuous slide. It did not happen all at once. It happened the way most collapses do, slowly enough that you keep thinking you can fix it until you can’t.
TL;DR: In one year I lost my business, my marriage, and most of what I thought defined me. Rebuilding was not inspirational. It was grinding, unglamorous, and slow. But picking one thing to fix each day eventually added up to a new life.
How it started
The business problems came first. Roofed Right America was growing fast but the partnership was fracturing. Disagreements about direction, about money, about how to treat people. I spent more energy managing the conflict with my co-owner than managing the company. Revenue was strong. The foundation was cracking.
The marriage was next. Not because of one thing but because of a hundred small things that accumulated while I was focused on the business. Amanda and I were co-existing, not partnering. By the time we both admitted it, there was not enough left to rebuild.
And then the business split happened. I walked away from the company I’d helped build to $35 million. Walked away from 180 employees. Started from zero at 41 years old with three kids who needed stability and a bank account that did not offer it.
The bottom
The bottom was not dramatic. It was quiet. Sitting in a rented apartment wondering how I got from $35 million in revenue to figuring out if I could afford takeout. That gap between who you were and who you are right now, that is where the real damage happens. Not the money. The identity.
I had defined myself by the company, the title, the team. Without those things I did not know who I was. That is a dangerous place for anyone but especially for someone who grew up without a parent and spent his whole life proving he was enough.
One thing per day
I did not have a master plan for rebuilding. I had a rule: do one thing today that moves you forward. Some days that meant sending a resume. Some days it meant going for a run. Some days the one thing was just showing up for my kids when I wanted to stay in bed.
Six months of that and I had momentum. Not success. Momentum. A new job opportunity. A better relationship with my kids. A therapist who helped me untangle the identity crisis. Small things that became a foundation.
What I built from it
The life I have now is better than the one that fell apart. Not because loss is a gift, that is the kind of thing people say from the other side. But because I was forced to build something on purpose instead of by accident. I chose the career, the relationships, the priorities. The first time around I’d just accumulated them.
I am not grateful for the collapse. I am clear-eyed about what it taught me. You can survive more than you think, but the surviving is not poetic. It is boring and repetitive and looks nothing like the inspirational posts on LinkedIn.
About Khary Penebaker
Khary Penebaker is a Regional General Manager at Great Day Improvements, overseeing operations across Chicago, Madison, Milwaukee, and Minneapolis. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership experience in construction, operations, and civic engagement.
Frequently Asked Questions
How do you rebuild after everything falls apart?
One decision at a time. You do not rebuild all at once. You pick the one thing that matters most today and you do that. Tomorrow you pick the next one. In six months you look back and realize you built something new.
How do you know when to quit versus when to keep going?
Quit the strategy, not the mission. If what you are doing is not working, change the approach. But if you still believe in why you started, do not walk away from the goal just because the path got hard.
Does failure make you a better leader?
Only if you are honest about what went wrong. Failure without reflection is just damage. Failure with honest self assessment is the best education money cannot buy.
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Last updated: March 25, 2026