Freelancing as a bird (lone bird in the sky)

Are you cut out to be a freelancer?

I wanted to be an astronaut when I was a kid.

I held on to this vision until 1986 when the Challenger space shuttle exploded just after lift-off — I was watching it on live television with my classmates and it’s an impression I’ll never forget.

It wasn’t long after that I decided I wanted to be either a magician or own a 50’s-themed diner.

The truth of the situation was:

I didn’t really want to be an astronaut; I wanted to eat space ice cream and float around in a puffy suit.

Freelancing is Not For Everyone

Just like I wasn’t really cut out to be an astronaut, not everyone is a good fit for freelancing.

Before I tell you how you can know if it’s a good fit for you, I want to define two types of freelancing:

  • Short-term: This is where you pick up gigs between jobs to keep the cash flow coming or maybe moonlight on the side for supplemental income. You’re not looking to grow a business or necessarily be “in it” for the long-haul. Freelancing is simply a nice way to use the skills you have to generate some extra cash outside of regular employment.
  • Career freelancing: This is a form of self-employment. You’ve hung out your shingle and you’re open for business with the intention of this being your primary source of income.

For the purposes of this post I’m focusing on “career freelancers.”

This sort of freelancing sounds sexy – I mean, who doesn’t want to have complete control of their destiny and call the shots?

But you’ve gotta ask yourself, do you really want to run a business or do you want to eat space ice cream and float around in a puffy suit?

9 Ways to Know if Career Freelancing is Wrong for You:

1. You’d rather have someone else make the decisions.

There is nothing wrong with this. Everyone’s wired differently and some may find it quite freeing to have someone else making decisions and setting the course. With that, you’re able to follow direction and feel a sense of accomplishment for doing your job well. But, if this is you, you’ll be an incredibly stressed out freelancer.

2. You think working from home is too hard.

When I tell people I work from home, I always get an interesting reaction. One of the most common is the thought that it’d be too tempting to watch TV or otherwise find ways to avoid work. Successful freelancers are highly self-motivated, so if you think you’re more apt to work in the garden than “go to the office,” freelancing is not for you.

3. You think working from home is so easy.

On the other side of the spectrum, there are those who think it must be so lovely to work from home – I probably get to meet my friends for lunch every day! To be sure, there are great benefits to having a flexible schedule, but it takes discipline to set boundaries around your work schedule and say no to distractions.

4. You like receiving a regular paycheck.

Who wouldn’t like to get a paycheck, right? The point here is that freelancing income is wildly inconsistent — especially for new freelancers who haven’t had time to get some systems in place to make sure there’s always a little something coming in or a big enough buffer in the bank. It’s a balancing act that’s difficult to manage.

5. You can’t afford (or dislike) risk.

A continuation of the previous point, going into business for yourself is risky — the odds of success are strongly against you. Depending on your life circumstances, you may not be able to take on the risk of failure. Or, you may just be a person who prefers a set routine and knows what to expect from day-to-day. Nothing wrong with that, but that’s not always the life of a business owner.

6. You’re reluctant to invest money to grow.

This goes hand in hand with risk. It’s tough to turn over those hard-earned dollars when you’re not sure you can re-coup the money. A successful freelancer sees the value in investing back into the business, because they’re confident they’ll see a return. This could be in the form of training, a new piece of software, and even knowing when it’s more profitable to outsource a bit of work than struggle with it yourself.

7. You’re uncomfortable being assertive.

Sometimes freelancing takes balls. Your paycheck is entirely dependent on your ability to go hustle up business. You need to have confidence in what you have to offer as well as a willingness to say no to opportunities that aren’t a good fit.

8. Your communication skills are weak.

You might think working for yourself from home means fewer interactions with other humans. That’s not the case. All day, every day, you need to communicate effectively with clients. The success of your business hinges on how well you can communicate. Take heart though, if this is the only thing on the list holding you back, this is an area you can work on and vastly improve.

9. You don’t have a plan for how to grow.

I assume you want to be more successful in 12 months than you are now? (By the way, success doesn’t always equal money.)

What are your plans to get from where you presently are to where you’d like to be? You don’t have to know all the answers, but you do need to have a plan. If you don’t, you’ll be buffeted along by whatever projects come your way and end up stuck in a place you don’t want to be. Successful freelancers make plans.

Well, does the shoe fit?

Freelancing is not for me.

There are so many choices we make everyday in life and so many directions we can go both personally and professionally.

Whether you’ve tried freelancing on for size and it wasn’t right for you or you’ve done some self-evaluation and know that’s not a path you should head down, then congratulations.

Why congratulations?

Because that’s one thing you can cross off the list. I don’t know about you, but for me, eliminating possibilities is the way I narrow down options.

Admitting freelancing isn’t for you doesn’t mean you’re a bad person or a loser – quite the opposite. It means you’re a person who knows yourself and is free to pursue work in an environment that encourages your success.

Freelancing is for me!

If you’re just starting down the path of freelancing, there are so many great resources to help you navigate the various aspects of freelancing: client relationships, billing, accounting, scoping, selling, managing, etc.

Below are a handful resources that I’ve personally used and found helpful in my journey:



Before I wrap this up, here’s a quick pro tip for taking on a new podcast: Scan through episode titles/descriptions and only download the ones that look most relevant to you. Downloading a history of podcasts is overwhelming. 🙂

Speaking of podcasts, I host a live weekly show called Each week I bring on successful freelancers and small business owners from the WordPress community. Since the show’s live, you can send questions and have them answered on the air. You can learn more about here.

Leave a Comment

Your email address will not be published. Required fields are marked *

Carrie Dils uses Accessibility Checker to monitor our website's accessibility.