You’ll Still Eat: How To Find Your Inner Entrepreneur

Matthew Maisano
Ascent Publication
Published in
5 min readJan 18, 2020
Photo by Oliver Sjöström from Pexels

It took me 36 years to figure out what I was meant to do. This article will take you less than 36 years to read, so you’re already off to a good start.

I have been an employee of someone else’s company for virtually my whole life. That time wasn’t wasted and gave me great value, friendships, and a ton of professional development. However, I was not paying attention to my inner entrepreneur.

From a young age, I was always figuring out creative ways to make a buck. Ever heard of a Multi-Pack? WELL, YOU SHOULD HAVE.

What happens when you take one stick of chewing gum from packs of Doublemint, Spearmint, Juicy Fruit, and Big Red and combine them into one package? Multi-Pack is born!

Photo by Gisela Merkuur from Pixabay

Yes, the extensive R & D efforts DO justify the 100% markup. You’re welcome Wrigley’s.

As I got older, the odd jobs continued. I ran the scoreboard at Little League games, dragged my friend out in the Connecticut winters to shovel driveways with me, and got doors slammed in my face selling questionably-legal prints of famous paintings door-to-door — the mailman and I discussed which brands of sneakers were best equipped for escaping very angry dogs.

This is all to say that I always gravitated towards independent jobs — jobs where the success hinged on me figuring things out largely on my own. Yet for some reason along the way of becoming an adult, I forgot these instincts. Until this summer.

This summer I decided it was time to quit my full-time job in media and start a production company. I want to build the company at which I’ve always wanted to work. This was both the most difficult and possibly the best career decision of my life. How did I come to this decision?

The short answer is that I finally figured out what type of environment I thrive in. I hope you’ll read this and see similarities in your career. Many of us go through periods of our careers and our lives where we feel like we are stagnating, or even that we’re lost. It’s very likely you just haven’t yet found your happy place. Let’s help you do that!

How To Know If You’ll Be Happier Working for Yourself

If you’re thinking more than one of these things below, there’s a good chance you may be ignoring your inner entrepreneur:

  • My work is the same it has been for years. Change is happening a lot slower than I would like.
  • I can do my colleagues’ jobs too.
  • I am a consistent high-performer yet I get the sense my opinions are not valued.
  • I work best when I am given more autonomy.
  • My work used to be more fulfilling.
  • I don’t fit in with this team, and that’s how it’ll always be.
  • No matter what I do, I can’t figure out how to advance here.

I put the most important one last. Whatever you do, don’t think that your track, your status, and — let’s be honest — your salary are indicative of your value.

Your life today does not define your life tomorrow.

The sooner you find the environment you thrive in, the quicker you will get where you want to be in your career. Where you are today does not define where you can be tomorrow.

Photo by Quintin Gellar from Pexels

Let’s say you’re thinking about quitting your job to start your own business. How do you know you’re ready?

Here are some key questions to ask yourself:

  1. Do you have at least six months of living expenses in the bank?
  2. Do you have a strong network of contacts in place (local or remote)?
  3. Are your skills advanced enough to command the rates you’ll need?
  4. Do you have secondary income streams available?
  5. Do you have a fall back plan?

After reading this, don’t be discouraged if you answered no to a few of them. Cue the cheesy-but-true self-help article line — you are capable of much, much more than you think!

Here are some steps you’ll want to take in the last few months before you quit your job to pursue the career you were meant for:

  1. Use as much PTO as you can to prepare. This is a valuable time to reconnect with old contacts and even take some paid rest before the chaos begins.
  2. Brush up on your skills. You can take an online course, attend workshops, or do anything to make sure you’re well-versed in the latest industry trends.
  3. Figure out the value of your benefits package, and build those numbers into your plans. It’s great to go into this knowing what the less tangible things you have, like company-provided health insurance, are worth.
  4. Start thinking about your workspace. It is hard to be everyone from the CEO down to the janitor, and someone’s gotta clean up after that quesadilla wrecks your digestive system. You’re in great shape if you get used to doing some of the less glamorous work beforehand.
  5. Get in the habit of deliberately planning time with your family and friends. Even if you are an introvert like me, you’ll be surprised at how much you may have depended on that social interaction at your last job.

You can read 100 articles about starting a business, and it still won’t prepare you for the highs and lows of being your own boss.

You can read that making your own hours is great (and it is) but you won’t realize how great until you do it. You can read that you’ll go through dry spells with no work, but nothing will prepare you for what it’s like to look at your bank account and legitimately considering selling your less-useful organs.

So what’s the bottom line? When you take the steps to create the environment that you personally thrive in, you’re going to be so much happier. When you have to answer to far fewer people, you’re going to be so much happier. When you realize that all those years of hard work can now directly benefit YOUR goals, you’re going to be so much happier.

Go get the career you deserve. It is going to be hard, and that’s ok. Nothing in life that is easy is worth it, and everything that is difficult is.

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Matthew Maisano
Ascent Publication

Filmmaker & XR producer always exploring how the latest media technologies can empower our stories and our audiences. https://bit.ly/2DXaFpN