You never feel ready, you need to look back, and it becomes who you are – how it feels to be an entrepreneur.

I’ve been my own boss for 5 years now and here’s what I can tell you with 100% certainty.

1. You don’t ever feel “ready.”

If you wait until you’re fully “ready,” you’ll be waiting for the rest of your life.


The great news is there are SO MANY resources available to you. We live in a time where most of us have access to an unlimited amount of resources.

Did you know you have access to Master’s degrees at MIT and Harvard for FREE? Barriers to information are minimal… meaning that’s no longer an excuse.

I remind myself daily that someone else has already gone through my newest challenge, and so the answers I need are out there.

You just gotta find them.

2. It’s easy to forget how far you’ve come.

Just last week, Ryan (the husband) was telling me about his friend who lives in NYC who is absolutely crushing it financially (in a crazy way).

But that he only gets 10 days vacation a year and works 50-60 hour weeks.

Wait a minute? Is that even worth it?

For us, the answer is no. When you are your own boss, you get to decide what success looks like for you.

Our priority is to be able to travel and never have to say no to a trip. I’m not even exactly sure how trips we took last year! Sure, we were working on many of them but we like our work.

I was able to go with my little sister on a trip to South Africa. I got work done during the day while she was teaching music as part of a mission trip. In the evenings, we got to explore together and stay up late chatting about life. I never had to ask off for work or sacrifice vacation days… I just said, “Yes.”

I set out to build a life of freedom 6+ years ago and sometimes I need to stop and remind myself to look back and appreciate my growth. As an entrepreneur, it’s easy to obsess about the future and forget how far you’ve come.

3. It creeps into all areas of your life… in a good way!

Being your own boss means you get to spend your life building YOUR dreams, not someone else’s.

As you gain traction, exactly how it looks day-to-day will likely shapeshift and grow alongside you, but never hold you back or limit you.

Being my own boss has also made me a better person across all areas of my life. It’s seeped into my priorities…

  • I’m excited for my days, so I don’t really feel like partying as hard when I have time off, by choice! It feels good to wake up with a fresh mind ready to own the day. 
  • I’m proud of what I do, so I get excited when I meet new people (I used to be SO embarrassed to tell people what I did for work).
  • I’ve realized many superficial things are really just ways of dealing with life dissatisfaction and I don’t really need them anymore (excessive TV watching, junk food, fancy cars, clothes, etc).

Don’t get me wrong, being your own boss has its ups and downs for sure. But I think being your own boss is the greatest adventure of all… because it’s *YOUR* adventure.