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Why every boss needs to fire themselves

Why every boss needs to fire themselves. Source: Getty
Why every boss needs to fire themselves. Source: Getty

This month marks my five-year anniversary of when I was fired from my business. It was a mutual decision between my business partner Frank Restuccia, our co-founder Jeremy Cabral, and myself. I was destructive. Like a tornado wreaking havoc everywhere I turned. I started resenting my work and people around me. I knew it was time to leave.

But it was the best thing I ever did.

The founder of a business will always be the visionary behind a great entrepreneurial idea.

However, it doesn’t mean you’ll be a great CEO.

Even Steve Jobs, the legendary founder of Apple was “fired” from his leadership role in Macintosh after launching what is now one of the biggest companies in the world. Many other founders have left leadership roles in their businesses including Jack Dorsey from Twitter, Travis Kalanick from Uber and Andrew Mason from Groupon to name a few.


Firing yourself from your business doesn’t have to mean leaving the business for good. It could mean stepping away from certain areas or roles, or some time away to pause and reflect.

When you’re in the heat of running a business it can be difficult to notice the red flags that indicate when it’s time to fire yourself. And if you overstay your welcome, you could be causing a toxic environment for not only your business but also for yourself.

I know it is tough. It could be the hardest decision you may ever have to make. But when you look back at that moment in time, it will probably be the best thing you’ve ever done.

Every founder needs to look out for these red flags and know when it’s time to go.

When you start becoming really negative

When you’re having a bad day, it can feel like there's a storm cloud of negativity following you.

This is what it felt like for me when I was at my darkest point. When the lens you see the business through is tinted and all that you see are problems with no solutions, step away as you’re doing more harm than good.

When you lose faith

A key trait of all successful entrepreneurs is optimism, which has to do with an ability to take risks and place things out of your control for the empowerment of the company as a whole.

This means you need to trust your crew and believe in their potential. If you find yourself losing faith in the people that are there to help you build your business, you need to reflect on this deeply.

When you bought a dog just to end up barking yourself

After developing an idea to then hiring your first employee, that is a huge milestone and every single person you hire thereafter is an incredible achievement.

But once you find yourself micromanaging and taking over their work, you have a serious problem. It means they are either not able to perform the role you hired them for, or they need some training, or it could mean you have some underlying fears about losing control.

For me, I would fly in and out of teams, isolate myself and disappear for days then come back in and shake everything up. I’d demand to change course in the middle of sprints, and I wouldn’t take ‘no’ for an answer. I was causing chaos. When you get to this point, you need to put the breaks on and step away.

Would your peers hire you for this job?

This is a key question to ask yourself. Do it often, because it forces you to reflect on your behaviour, and review your performance as a leader.

What are the qualities, skills and traits that your peers look for in a hire?

What personality type and values? And arguably the most important question to ask yourself, how do you fit into the team culturally?

If you’re not the kind of person they would hire for the role you are doing, then you need to ask yourself why you are doing this role.

No enjoyment from your work

All of these previous red flags have one thing in common: they suggest the work environment you are in doesn’t bring you happiness and fulfillment.

You need to ask yourself if this is the work you really want to do and what exactly is making you so unhappy with your work. For me, I was dealing with loss and grief from moving on from my role, I felt a loss of control, I expected everyone to be disappointed if I wasn’t there. I lost faith in myself.

Ultimately, It is key to never feel ashamed if you notice yourself suffering with one of these symptoms. Acknowledging that it’s a red flag that needs to be addressed is the first step towards finding your happiness in what you do and helping your business succeed.

Fred Schebesta is a Founder of leading comparison website Finder and the Finder app.

Read next: How $193 million CEO bounced back when Google wiped out his business

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