How Starting To Freelance Is Like Learning To Riding A Bike

The other day I was at the park with my oldest daughter Daphne, who is 5 (and a half…if you were to ask her).

A bunch of kids had brought their bikes, but Daphne doesn’t really ride hers much these days.

She used to love riding her bike and would always do laps around the playground, giggling and super confident.

She still uses training wheels, and a lot of her Kindergarten peers are starting to ride without them.

I can see it’s starting to knock her confidence a bit. And now, she hardly wants to ride at all.

As I was watching her that day at the park, bike-less, I wondered what my husband and I could do to get her to learn to ride the bike without the training wheels?

  • Take her shopping to buy a new big girl bike
  • Read a book all about bicycles and riding trails
  • Watch YouTube videos about the cool things she can do once she ditches the training wheels
  • Expose her to other kids at the park riding bikes without training wheels

We could totally do all of those things, but realistically I know she’s going to have to actually get on the training wheel free bike and practice.

Easier said than done, I know.

We’ve taken her around the cul-de-sac by our house and up and down the driveway to practice before without the training wheels, and it pretty much always goes the same.

“I can’t do it.”

“It’s too hard.”

“I’m never going to be able to figure this out.”


That’s when it clicked: this had nothing to do with Daphne’s capability at all.

It had to do with her mindset.

The funny thing is, I see this over and over again with the mamas who are considering a freelancing business.

You see the other mamas doing it, and it looks fun and amazing and like an amazing path towards financial freedom and flexibility (it is).

And yet, you tell yourself that you can’t do it.

You watch videos about freelancing.

You may even invest in a course about freelancing.

But you never actually take what you’ve learned and get on the bike, so to speak.

You cannot learn how to ride a bike without actually riding, and you cannot become a freelancer without actually freelancing.

You’re afraid to start freelancing.

The last time Daphne told me she couldn’t ride her bike, I told her “you’re right. If you keep telling yourself that you can’t ride the bike without training wheels you’re right, you won’t be able to.”

One of my favorite quotes of all time is from Henry Ford. He said, “whether you think you can, or think you cannot, you’re right.”

We’ve been working on Daphne’s mindset about riding a bike. We talk about what the worst thing that could happen is (possibly falling and ending up with a band-aid-worthy scrape).

You have a reason why you are starting to freelance, whether it’s because you want to quit your job or help financially to ease pressure off your spouse or find professional fulfillment.

Let me tell you – nothing is holding you back, but you!

What is the worst thing that could happen if you took the plunge?

You go back to a 9-5? You’re probably already there!

If you tried to get a client?

They say no? That’s not the end of the world.

If you tell a less-than-supportive family member?

Now…if you took your training wheels off and really launched your freelancing business…what’s the best that could happen?

Are you going to continue to tell yourself you can’t do it.

Or are you going to ride the bike?


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