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Are You a Failure if You Go and Work for a Boss Again?

Mar 3, 2022 | 🌈 Entrepreneurship

In my entire post-graduate career, I only ever worked for a boss once – for 1 year. And now, that’s already 5 years ago. 

All the other time, I’ve been either setting up businesses or I’ve been working as a freelancer. Usually a combination of both. Going back to work for a boss and being an employee again was never really an option in my mind.

Until today 😅

Today I had a really nice call with two people from Tinqwise – a cool Dutch scale-up that creates learning solutions for mainly corporate clients. I had originally reached out to them to collaborate on a freelance basis (which they liked), but they also proposed exploring other options. Like an actual job. And I thought: well, why not?

It certainly can’t hurt to make new connections with people in my industry. At the same time, it’s a nice opportunity to learn and understand my own position in the market better. 

Of course it also made me think: how bad would going back to working for a boss actually be? Let’s make a pros-and-cons list!


Con: “I would feel like a failure” 🥲

This is the first thing that popped into my head. I’m pretty sure it’s the same for the majority of entrepreneurs who are considering to work for a boss again. 

We might think something like: “going back to work for a boss would make me feel like a failure. Like I couldn’t make it on my own as an entrepreneur. Besides, I would have to ask for permission again to go on vacation. Like a caged animal. Why would anybody want that?”.

The thing is: we are what we tell ourselves.

If you’ve read any literature relating to entrepreneurship at all – like Mindset by Carol Dweck or Think and Grow Rich by Napoleon Hill – you know the incredible importance of mindset. You know that what we tell ourselves, and what we think of ourselves, has the power to change our entire lives.

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So you’re only ever a failure if you allow yourself to think that way. Other narratives could be that you’re brave for trying something different. Or that it’s a stepping stone to something greater. Or that you’re able to help more people this way. 

Or that it will enable you to accelerate your personal development, which brings me to my next point.

Pro: “I could accelerate my learning” 🚀🎓

If you work in your own company, you don’t necessarily get a whole lot of feedback. You might, if you have that kind of relationship with your employees or co-founders. But it’s still something you would have to trigger yourself somehow.

While I (nearly) always ask for feedback from the people I work with, I noticed that it’s hard to get really critical and constructive feedback. Especially, because in nearly all cases, I’m the expert. I know most about the stuff I do. 

What could be great about working for a boss is that I surround myself with other experts. Other people like me, which may be working in entirely different ways.

Sure, I could get in touch with such people as an entrepreneur too. Maybe by setting up a mastermind, or by attending certain networking events, but I would never get to work with them as closely as when working for a boss. 

So yeah, I do believe that when the job is right, I could learn a lot more, a lot faster than when I would continue to work for myself.

Con: “I would have less time to work on my own businesses” ⏰

It’s a simple calculation that when you work 8 to 40 hours for a boss per week, you’d have less time to work on your own stuff.

But if you still have that time now: how much do you truly spend it on valuable things? 

If I speak for myself, I’m a master of procrastinating. When there’s a task that’s unclear or something that I dread doing, it can sometimes take weeks before I pick it up. If I even pick it up at all. 

Though when your time is more limited, you might start using it efficiently. 

There are countless examples of people who built incredibly successful businesses next to having a full-time job, like Ali Abdaal. He worked as a doctor during the day, while shooting YouTube Videos in the evening for several years. Now he makes over 4 million dollars per year through his YouTube channel.

There is a chapter in Steal Like an Artist by Austin Kleon, which does a great job at explaining the value of keeping your day job.

As long as your day job doesn’t fully drain you of energy, you will be able to spend your evenings productively on doing something you like. You might even be more productive when you no longer have to work on acquisition, worry about finances or do your bookkeeping. 

Pro: “I could have more fun” 🎈🥳

I speak to many freelancers and what I notice is that they often love the work they do, but… they also often work alone. Behind their laptop. At home.

It can feel lonely at times. It certainly does for me. So lonely, in fact, that I felt compelled to start a community for entrepreneurs

So being around people. Feeling part of a team that likes the same stuff I do. It could be a lot of fun. Even if it’s just for one day per week. It could just give you that boost of inspiration to run your own business(es) with more passion and energy.

And we certainly shouldn’t underestimate the value of Friday drinks or company trips. People are social animals. Being around other people fuels us. That even counts for introverts like me. Just, maybe not all the time.

I still like creating in my own little bubble a little bit every day.

Conclusion 💡

I hope you enjoyed reading this short list of pros and cons. Of course, you could come up with more, but these are the few that feel most relevant to me. 

And to my surprise… the cons aren’t actually that bad right?

I didn’t mean to turn this article into an argument in favour of working for a boss again at all. But I like how it turned into that. Because I think a lot of entrepreneurs need to hear this:

“It’s OK to work for a boss. Really.”

I’ve seen so many entrepreneurs that were slowly destroying themselves. Getting burnouts. Feeling like failures (while being a full-time entrepreneur). And then, when they finally decided to get a job again, they felt happy. Like, genuinely happy. And that’s awesome, isn’t it?

One important thing to realise is that working for a boss isn’t the end. Not at all. It could be temporary. It could be part-time. It could be interim as a freelancer even. And it’s never too late to go back to being a full-time entrepreneur again when you feel ready – like when you were able to build some momentum with a side hustle, for example.

Do what feels right for you right now. At the very least try stuff out and allow yourself to discover what feels right 🤠

Don’t be miserable as an entrepreneur just because you feel like you have to grind it out. Live now! Spend time with your loved ones. Make sure that if you die tomorrow, that you are happy with how you spent your time. And maybe that means working for a boss, even if it’s just for a little while.

Oh and as for my own decision of whether I’ll be working for a boss again anytime soon? I don’t know. Time will tell.

Either way, I’ll keep you posted!