3 reasons to start your own business and 3 reasons to run like Hell from it.

Ja-On Hillman
3 min readApr 17, 2022

It’s like nails on the chalkboard to my ears when I have people say, “You are SOOO lucky, you have your own business!”

Photo by cottonbro from Pexels

You felt that right? The metaphorical scraping down the chalkboard? That vibration down to the bone, and if you own a business, are self-employed or even freelance, you’ve heard that sound.

“You’re SOOOO lucky…”

I might be a little over-sensitive about this, but if you’ve been in that position, you know how it is. You have to take it like a compliment even though you know for damned sure that there’s nothing lucky about it.

It’s a lifestyle, a mindset, and sometimes it just plain sucks.

If that sounds paradoxical, let me break it down into the good and the bad.

The Good

  1. You get to create your own future! It’s up to you and all in your control. The ability to take charge, make the decisions and create a valuable product or service that you can provide to your customers is a powerful thing.
  2. Flexibility! People are correct when they say you have more flexibility than a job can provide. I love being able to take a day or weekend off to be at a sporting even for the kids or if a sick day was needed. Having real flexibility like that is one of the major reasons I chose my career when I was young.
  3. You can be your own boss! Knowing there is no-one but yourself to answer to is a liberating feeling. Deadlines are created by you and fulfilled by you, not by some overlord who gets acclaim for the job being completed. There’s no applying for budget increases if you need a new computer and no need to justify having to buy nicer stationary. This is your business, you get to make the rules.

The Bad

  1. Sometimes you get paid! You heard that right… sometimes you will get paid. Having an amazing product or service is one thing, but having a target market that actually wants to give you their money? That’s an entirely different beast. Not only is finding customers not easy and takes longer than we want, we still have the dreaded accounts receivable… some clients simply don’t like to pay.
  2. Flexibility can create problems! It sounds amazing to be able to pick and choose your hours, but if you pick hours that clients don’t want, they won’t give you their business. Customers love consistency, and if you confuse a customer, you lose the customer.
  3. Your boss sucks! Yeah, sure you can choose when you want to work, but the reality is that you will punish yourself for taking time off. Entrepreneur guilt is a real mind game. And let’s talk about pay raises… do you know your value and are you willing to stand by it?

Is it worth having your own business?

The answer, of course, it… It Depends.

If you want to make more money, it’s probably not your thing. There are certain skills you will need to learn and perform well, above and beyond the business you want to run.

For example, if you are a massage therapist and want to open your business, be aware that having those skills is great, but all the other business related skills will need to acquired… and they take time away from doing what you are truly good at.

If you want to create a business that is greater than what you can achieve on your own and create an asset class that is saleable, then explore the option. Just remember you will be doing less of what you love, and more of what you may not.

Conversely, there’s a happy medium called the Side-Gig Entrepreneur…

Thanks for reading! If you want more tips on unlocking inner health or creating a life-changing side-gig, sign up for my free newsletter below and learn more about the Side-Gig Entrepreneur concept!

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Ja-On Hillman

How I hate the term, "Lifestyle Design", and yet it is best phrase to use. Over 20 years in Health Care and Entrepreneurship, Automating Cashflow here on out.