Entrepreneurship vs Employment: Which One is Right For You? - Jenna Kutcher

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Entrepreneurship vs Employment: Which One is Right For You?

Jenna Kutcher 

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I’ve gotten a few things right – but I’ve also gotten some wrong. For years and years, I sold entrepreneurship as the right path for everyone, because for me, it unlocked a life better than I ever dreamed. But the more that I know about entrepreneurship, the more that I evolve and grow as a leader, and the more that I learn about all the different ways we as humans are wired to show up, I recognize that for some, being an employee IS the dream! So let’s talk about the pros and cons of both and how to distinguish if you’re better off as an entrepreneur or an employee! 

In this episode, I’m sharing the perks of being both an employee and an entrepreneur, seven signs you’re ready to become an entrepreneur, how to face your fears around starting a business and the one exercise that I did before I left behind the 9-5 life forever.

My Employee History

There are a TON of reasons I am obsessed with entrepreneurship. I haven’t set an alarm for years – though now my kids are up at 5 a.m. anyway! I can make my own schedule, work from anywhere with wifi and my laptop, travel the world, experiment with new ideas, be in charge of my earning power…I LOVE entrepreneurship. 

But I worked a LOT of different jobs as an employee before I ever became an entrepreneur. I am a first generation entrepreneur and the first of my family to go into full time entrepreneurship. There was definitely some fear around the move from employee to entrepreneur.

Let’s start with a few distinctions between being an entrepreneur and an employee: 

  • Employees seek guidance while entrepreneurs like to create the plan. 
  • Employees tend to take less risks whereas entrepreneurs seek risks out. 
  • Employees get paid for their role, entrepreneurs get paid for their results. 
  • Employees follow rules whereas entrepreneurs tend to break them. 
  • Employees are responsible for some decisions, entrepreneurs are responsible for all.
  • Employees work to a schedule, entrepreneurs make their own. 
  • Employees tend to be more social where entrepreneurs tend to be more siloed. 

Things I missed when I became an entrepreneur: 

  • Paid time off: My first few years I barely took even a day off of work. 
  • Feedback on performance and help with goal setting/vision casting. 
  • The ability to close the office door and leave work at work. 
  • Coworkers and peers to communicate with and do life with. 
  • Having a more clear plan/trajectory and vision for my life. 
  • The significance that having titles gives you – I felt like I had to prove myself.

Not For Everyone

It’s been super interesting because in my experience entrepreneurship has unlocked so much for me. It was like I was addicted to how it changed my life that I wanted everyone and their mom to know about it and do it, too. If you would have asked me a few years ago, I would have swore that everyone should become an entrepreneur. 

Maybe it was the pandemic and seeing how essential workers changed and saved lives or just the acknowledgement that with ALL of the benefits and pros of entrepreneurship, there are also a lot of stresses and responsibilities that can be a lot to handle.

As an entrepreneur, the last few years have left a lot of us questioning if we’re cut out for it, if we can really do it. I know I felt a TON of responsibility and weight over the last two years in making sure everyone was fully paid and supported by my business. We introduced things like full paid maternity leaves, got my employees 401ks and some of those bigger things that you don’t really think about when you start a business. While I wouldn’t personally trade being an entrepreneur for anything, there’s a lot to it. 

Regardless, I started to have my eyes opened more that the world can NOT be filled with entrepreneurs, in fact, my business would not run if everyone and their mom wanted to be an entrepreneur because surprise surprise, I have a team of about ten employees and contractors and that’s how all of this is possible. 

Reasons to Love Employee Life

In fact, in preparing for this episode, I asked my team why they enjoy being an employee and what that looks like for them personally! Here are a few points they made that I love.

Not having to think about paying your own taxes out of your earnings as an employee is one benefit. A big theme was financial security as an employee. Income is more or less guaranteed as an employee which is a perk but also downside is that it’s rarely scalable.

Other perks include benefits in general like paid time off, retirement/401K’s, and healthcare since that can be hella expensive as an entrepreneur. 

Other perks include being able to ideate/collaborate with brilliant brains who are all driving for the same result in a more intimate way. 

Being able to shut down at the end of the day without the weight or responsibility of entrepreneurship – like the pressures of building and maintaining a brand/product/self reputation, that isn’t for everyone!

Not everyone wants to (or is built to) be the center of attention and life of the party. Some of my team are more wallflowers, observers; happy to work in the background as part of something bigger and meaningful, without the attention and scrutiny that come with being the face of a brand and business.

More from This Episode

Tune in to hear a deeper discussion and my thoughts around entrepreneurship versus employment. I also share some clues that you might be ready for entrepreneurial life. Press play above or find the episode wherever you get your podcasts.


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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