Seek discomfort

A follow-up article about comfort zones and freelancing

Hi Friend,

If you’ve been a subscriber for long enough, you might remember my post on pushing yourself outside your comfort zone.

Photo by Jackson Simmer on Unsplash

I firmly believe that successfully running your freelance business requires you to do things that make you uncomfortable. Not illegal things (obviously), but things you aren’t natually drawn to do.

Things like:

• Sending out pitches

• Sending connection requests on social media

• Following up with clients who don’t pay

• Charging more money

• Marketing yourself (which I advise freelancers to refer to as business development if they don’t like the words “marketing” or “networking”)

This recently came to the front of my mind

(or the top of my mind?)

Earlier this week, I read an article in Never Retire: Living the Semi-Retired Life (a fantastic newsletter by Rocco Pendola—I recommend subscribing, especially if, like me, you see yourself never fully retiring from work). His closing note was about a motto from a YouTube channel. That motto is “Seek Discomfort.”

In this case, the people at Yes Theory are talking about living a life of great moments by seeking out discomfort. Doing the things that make you uncomfortable. (At least, that’s my takeaway having only briefly glanced at the YouTube channel—which highlights skydiving and triggers all of my “Oh my god, never in this lifetime” reactions).

But the same is true for running a successful, sustainable business. Running a business without doing things that make you uncomfortable is almost impossible. If nothing in your business makes you uncomfortable, you are either the most laid-back person on the planet or you’re not pushing yourself.

I’ve heard from learners who felt their business wasn’t as successful as they wanted. I’ve been on panels where an attendee yelled at us because his business wasn’t making money (it was a deeply uncomfortable situation). I’ve known people who started freelancing with dreams of unlimited income, only to find themselves charging the same rate 10 years later because they never increased their fees.

The problem has little to do with each individual’s writing or editing skills. It’s also not about how smart they are. Most often, the issue is that they weren’t willing to make themselves uncomfortable. Truly, a lot of average people have wild success, often because they’re more willing to push themselves.

Note: I’m not saying this is the only reason freelance businesses end, but it’s a big one.

Discomfort isn’t just about finding clients or charging money. It’s about:

• Pushing yourself to work when you don’t feel like it.

• Setting boundaries around your work time and personal time.

• Sitting at your computer even when there are no looming deadlines so you can move your business forward.

• Taking Zoom meetings even though you feel socially awkward.

• Saying “no” to scope creep.

The things you feel uncomfortable doing are almost always the things that will stop your business from being as successful as it can be. And that means you have to figure out a way to either tolerate them, even if you never fully embrace them.

How do you do that?

By doing them. By doing them until they become comfortable.

And by remembering that nothing is as uncomfortable as having your business fall apart without you doing everything you can to keep it going.

Think about it, what’s more uncomfortable:

• Having someone ignore your connection request on LinkedIn? Or having your business fail because you can’t find clients? (Trust me, I’ve forgotten more ignored LinkedIn connection requests than I can count.)

• Having clients annoyed that you followed up on an unpaid invoice? Or explaining to your cell phone company that you can’t pay the bill because you haven’t been paid?

• Being told by an editor that they aren’t interested in your pitch? Or knowing you have a great idea that was never published because you didn’t even try?

If you truly want a successful, sustainable business, you’ll have to do things that make you uncomfortable. The more you do them, the more comfortable you’ll be.

Choose discomfort now so you can have greater comfort in the long run.

Here’s what you can do

Write a list of all the activities you’re involved in as you run your business. Keep it handy so you can add to it as activities arise.

Put a star next to the ones that make you uncomfortable. The ones you put off for four or five days or hope will resolve themselves because you don’t want to deal with them. The ones that make you regret ever starting your own business.

Pick one or two of those activities and commit to doing them immediately when they come up—no putting them off, no excuses.

If taking Zoom meetings makes you uncomfortable, say yes to every meeting suggested. Reach out to people to initiate meetings of your own. Ask a friend/colleague/mentor to practice meetings with you.

If sending article pitches terrifies you, do it. Commit to sending X pitches every day. Do it so it becomes second nature, so receiving a rejection letter doesn’t rock your emotional well-being.

Once you’re more comfortable with those activities, choose more to engage in.

Four years ago, I avoided meetings like baby rabbits at the park avoid my dog. I only conversed via email (and, if absolutely necessary, phone). But I realized if I wanted higher-paying clients I needed to push myself to take meetings. So I did. I started saying “yes” to every meeting that came my way.

Last month, I ran a meeting with around 20 people representing various content teams at a Big 5 bank (that’s a thing in Canada). And now they’re implementing some of the suggestions I made. I don’t know if I could have done that four years ago.

Pushing myself to take meetings enabled me to take on these kinds of projects, which allowed me to charge more for the work I do.

I know it sounds scary, but, tough love time, you need to do it.

Seek discomfort.

Feel like sharing something that makes you uncomfortable? Or a tip to move past discomfort? Comment below!

Here’s to your ongoing freelance success,

Heidi

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