Why I’m trying to fire myself (And How I’ll Pull it off)
You might know this feeling.
It’s Friday evening. I should be just about logging off for the day.
And, within 20 minutes—three requests come in over Slack, Asana, and Email:
- Boss, can I get access to the corporate credit card. I need to start tracking emails, which means buying Yesware. I’ll get you the Lastpass login.
- Chief…I gave the customer a refund. When he switched plans, something went wrong, and we really needed to make that right.
- Dennis, I really need someone to help out with a banner design for next week. Can I add a project to Upwork?
Now, any manager’s inbox can look like this. You have a handful of people who rely on you for decisions.
But I realized, if you really want to grow a company—these questions are a sign of a bottleneck.
And that’s what I’d become—a bottleneck. A micromanager. I’d hired mini-me’s who were good in one very specific corner—at sales, or at development, or at support. But the second they needed to branch out or make bigger decisions—it all came down to me.
And as I was having this realization—I noticed my wife looking over at me. Or more so, she was looking at me, looking at my phone, on a Friday night.
I’d already gone through one divorce.
I had to quit my addiction to managing every detail of my company—if I didn’t want to mismanage what mattered in my personal life.
And I didn’t have a single idea as to how.
Fast-forward through the dread and onto a more positive bit of self-reflection.
I was talking to my cofounder Claudiu, and we realized that there is something that sucks a lot more than being the boss.
Being the employee of a bad boss.
To get where I had gotten—I had failed a lot. I’d learned a lot, too. From picking tomatoes at 4 am, to burning a year’s salary in savings to launch a tech startup. Throughout it all, I had come to believe that there were many decent bosses. But few of them were coaches.
And they all taught me to work towards personal freedom.
And not the Facebook Ad Life Coach “Buy My Personal Freedom Starter Kit for $299” sort of freedom.
The kind of freedom where you can pursue something interesting. Where you can evolve. Where you’re not limited by the emotional or logistical barriers of the 9 to 5. Or the job description you were hired for, or the cubicle, or the old school ways of thinking about work.
The kind of work I loved to do was the type that pushed me closer to my personal goals—where I was learning the skills I needed to build my own company. I was lucky enough to have bosses that treated me like a partner. Where we shared knowledge, and trust, and, for 4-5 years, we mutually invested in a shared journey.
Those were the good bosses.
The bad bosses were the ones that taught me to see the requests coming in on a Friday night as a red flag. They were a sign that I was on my way to becoming a bad boss.
When TED-talks don’t suck
I have a love/hate relationship with TED-talks. But let’s discuss what they do well…they inspire. They motivate you. They have you (intellectually speaking) eating out of the palm of the presenter’s hand.
Thanks to Facebook algorithms, my feed is loaded with Ted Talks. A couple clicks, a few video watches, and an occasional page like—and I can no longer avoid the name, Brian Robertson.
“Holacracy as the way out of hierarchy” came my way at the same moment I was learning about unschooling—or, trusting my children with the freedom to learn however they learn best.
If that’s what I valued for my kids, and valued for my family—why on earth was I still managing my employees with hourly rates, Upwork screen records, and instruction manuals?
So, I watched a talk on Holacracy. And as Brian Robertson gives his pitch, I realize that Holacracy is about employee empowerment—about building a team and making them equals on the journey of entrepreneurship. He discusses why the structure of a company should be based on employee feedback, rather than layers and layers of management.
And Claudiu and I thought this was something we should try.
Throw away the instructions manuals and double the pay
Holacracy found us at the right point. I was tired of micromanaging. As founders, Claudiu and I realized we were happy with our monthly salaries.
And as we looked at the team, we realized—it was time to move away from low-cost freelancers, training manuals, limiting job descriptions, and the “do as I say” mindset. We had built a company that was limited to the knowledge of the founders. Little to no new ideas came to us from the team.
So, from this point on, we decided to…
- Set a revenue goal where each new dollar was divided equally throughout the team.
Now, as the company made more money, the team made more money. As the founders, we’d realized we no longer had to worry about things that used to keep us up at night: rent, insurance, seeing our families, or saving something for the future. We didn’t want anyone else on the team to have those concerns either.
My “lose sleep over it” worries used to be: traveling long distances to see my daughter, and offering health care and a living to the six people I support. There were several others—but they all revolved around my roles outside of work: as a father, husband, brother, and son.
These were things I shared with my team. And they shared their stories back to me.
And through that act of transparency—we found the common threads, and we set up a plan to fill the “worry” gaps with revenue growth. It’s a journey we’re still on today.
- Holacracy. Freedom with structure. How do we do it?
We decided we liked the idea of Holacracy. We just didn’t fully understand what it was.
So we hired Morgan–who became our “Holacracy Bootstrapper.” The job, at first, was just to figure out how holacracy works, how it could work for our remote team, and how we would go about getting started. I trusted her with the massive task of integrating Holacracy into our organization—and we began to see the company transform. Now, we trust every team member to be their own “boss,” survey what needs to be done to meet our goals, and to move themselves, and Convert, to the next level.
- Find the future entrepreneurs (and let the “employees” go).
Inevitably, some team members couldn’t step away from the manuals. And we had to let go of a few who weren’t quite up for the transition.
But, most of our core, full-time team members were fast to embrace the trust, and reinvent their jobs.
With salaries rising, and autonomy growing—something magic started happening. Little by little, I moved away from most operational tasks. In September, I signed off on two team members I never saw, met, or interviewed. I could trust their future colleagues to make the right choice.
Make no mistake, there are still things I’m in control of. But I don’t sign off on trial email flows. I don’t sit in on demos. I trust the Customer Happiness team when they refund a customer account.
The company is run from the outside inward. My colleagues who talk to the customers, know the customers well. When they say they need an integration—we build an integration. When they buy tools, I trust they will use them.
Roles, and the people who fill them have a budget. Every person has a credit card on Emburse—with limits that correspond to their role. Whether you’re in Madrid, Bangladesh, Chicago, or Cancun—we can trust you to do the right thing.
Which means I don’t have to sign off on a 19.95 Yesware subscription on a Friday night.
My life back!
I tried to build a 4-Hour Work Week company—a company based on systems and outsourcing.
But it’s not for me.
I don’t want systems to run my company. I don’t want to pretend I’m the smartest guy in the room.
I’ve reached an age where I’d much rather like to share what I’ve learned. Where I hope to see my colleagues as people that have their own dreams. And where I’ll try to help them grow—giving them the freedom to change, swap roles, or leave and become their own entrepreneurs.
Convert is thriving. It’s the company I wished I worked at 25. It’s a pleasure to motivate people, help my colleagues when they’re stuck, and little by little, dismantle the “bad boss” within me.
With shared failures, humblebrags, and the courage to be assertive—we are a building a company where team members are happy. Where their needs come first. And that’s the kind of company that our customers are happy to work with.
So now, I’ll get back to my other job—putting my 3.5 year old to bed. It’s 2 pm and he really needs his nap. Just like his dad.
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