February 5, 2020

The Hard (& Happy) Truth about Being your Own Boss.


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About five years ago, I left my high-paying, well-respected corporate job to start my own business as a transformational coach and run my own retreats. 

Except for when I’m leading a retreat, I am completely locationally independent. I can take my coaching calls, create transformational content, and work on my retreat business from anywhere. I get to create my own hours, and decide my own salary.

And I get to make a massive difference in people’s lives, while expressing myself creatively.

Because of all of this freedom and fulfillment, many of my clients and friends tell me that they want to create a career as a virtual entrepreneur for themselves.

There is so much hype and glamour around virtual entrepreneurship, but there is very little real talk about it.

So I decided to create a pro and con list for those who are virtual-entrepreneur-curious:

Pro: you get to decide what you do each day!
Con: you have to be the one to decide what you do each day.

Pro: how much money you make is completely up to you!
Con: how much money you make is completely up to you.

Pro: you can travel and take time off whenever you want!
Con: you can travel and take time off whenever you want.

Pro: you are your own authority figure!
Con: you are your own authority figure.

Pro: you get to create your own credibility!
Con: you have to create your own credibility.

Pro: you get to do work from anywhere as you travel!
Con: you often have to do work as you travel.

Pro: you don’t have to clock in and clock out!
Con: you don’t get to clock in and clock out.

Pro: what you do is what you love, so you think about it all the time!
Con: what you do is what you love, so you think about it all the time.

Being self-employed can be lonely. Confronting. Exhausting. If your business isn’t doing well, there is no one else to blame and often no one to even complain to. Often your friends with nine-to-fives think you have it made.

It is hard to establish boundaries, which makes it easy to either over-work or over-play. It can be hard to ever feel like you’ve done enough. 

You have to be your own boss. Your own HR department. Your own cheerleader.

But at the same time, being a self-employed entrepreneur can be incredible. I took a four-month road trip with my boyfriend and traveled to four countries this year, and I was able to do what I love all along the way. 

I got to help transform the lives of hundreds of people while I lived the life of my dreams.

But that doesn’t mean it’s been easy.

There have been days when I have desperately longed to have an office I could go to, with other people around, set hours to work, a boss telling me what to do and a standard, reliable paycheck.

There have been days when the possibilities of what I can do with my time and my career have been paralyzing. 

There have been days when I don’t want to take full responsibility for my business. When I just wanted someone—anyone!—to tell me what to do.

So if you think that being a virtual entrepreneur will fix your problems, just remember: wherever you go, there you are.

Whatever job you work, it’s you working it.

I know plenty of people who became self-employed thinking that it would fix their money or time or freedom problem, their issue with authority, their creative frustrations, or their self-worth challenges only to find that the same issues followed them into their self-employment.

You can work a nine-to-five and be happy and fulfilled. You can be self-employed and be unhappy and unfulfilled. It’s not about what you do, it’s about who you be.

You can quit your job and go to Bali, but if you’re not dealing with your sh*t, it’ll come with you to Bali.

Pursuing virtual entrepreneurship can be another form of escapism. Use discernment. Get crystal clear about why you want it.

It’s not about what you do on the outside, but rather about whether you choose to see every challenge as a growth opportunity or not, and whether you are really willing to deal with your own sh*t. 

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