When you feel trapped in your “successful” freelance business, do this

One of the funnier misadventures I’ve had while being self-employed happened in October 2019, and it’s the perfect story to illustrate what happens when freelancers aren’t clear on what they want.

A software dev team had flown me up to Toronto and put me up at a Best Western in Newmarket so that I could guide them through a 2-day branding sprint.

Getting outside always helps me feel a bit more grounded and human when I’m traveling, and Google Maps showed a park, nature preserve, and network of hiking trails across Yonge Street behind Upper Canada Mall. “Perfect!” I thought. “That’s where I’ll head during my morning run!

That Thursday began as planned. My alarm woke me up, I put on my workout clothes, and I jogged through parking lots and residential streets to the splotch of green I’d seen on the map. I fell into an easy pace between 9 and 10 minutes for maybe 3 miles. All was right with the world.

Then, as woods gave way to more woods, my phone lost the signal. Was I even on Dave Kerwin Trail? I had no clue.

My anxiety started to ratchet up when I checked the time and realized that my thirty-minute run had stretched to over an hour.

Being lost in a forest on your own time is one thing, even a good one at times, but being lost when a client is paying you $1000s to help them solve a business problem and is wondering where the heck you are and why you aren’t responding to texts and calls? That’s just embarrassing.

By the time I finally took the right path that led me out of Peggy’s Wood Park—thanks for nothing, Peggy—I had maybe fifteen minutes until my client, Kostiantyn, picked me up at the hotel. The Maps app and GPS on my phone, now suddenly so eager to serve, showed I was still a good mile and a half away. I checked Uber, and waiting for a ride would have taken longer than running back to the hotel.

Well, biscuits. I had to swallow my pride, text my client to explain how I’d gotten lost in the woods in the middle of the suburbs, and ask to start our work later so I’d have a chance to hoof it back to the hotel and shower.

To their credit, the client was all grace and “I’m glad you’re okay” when he picked me up. We were still able to get the insights we needed that day. All’s well that ends well.

We need three things to navigate.

There’s a reason smart runners rely on cell towers in unfamiliar places and instead wear a GPS watch.

Runners can’t always know what’s around the next bend, and that’s certainly part of the appeal. That morning, I was eager to explore, and I was grateful as dawn broke over the mirror-smooth surface of a pond. I was hemmed in on all sides by trees and silence.

At the same time, such gratitude can quickly turn into anxiety if you come to a fork in the trail and don’t know which path will take you where you want to go.

Some of the freelancers I chat with have the same feelings I did that October day. They’re running circles in the woods because they don’t know which way to go.

To navigate, we need three things:

1. GPS (or, Map)
2. Bearing (or, Direction)
3. Fixed Destination (or, Goal)

When I was gallivanting around the wilds of Newmarket, I had a destination in mind: my room at Best Western. Once I had a signal again, my Maps app could help me go the right direction. It could exactly how far to go and which turns to take.

Freelancers struggle because we have a rough map (like “become a well-paid freelancer” or “make more money in less time”) and a vague bearing (like “get better clients”) but no fixed destination.

Feeling trapped in a “successful” business

Even if they’ve got a clear idea of the lifestyle they want, freelancers often lack clarity around the business model, including the offers or productized services, prices, and processes they need to travel that direction.

The converse is also true: You can have a business that makes money and yet guarantees you enjoy your life less, not more. I hear about this situation at least once a week when someone reaches out to me about 1-on-1 freelance business coaching because they feel trapped in a “successful” business:

• “I’m on the content writing hamster wheel and have been burning out… for a long time.”
• “I’m working many nights and weekends, but feel like I can’t say no, especially to loyal clients.”
• “I do too many different things for too many clients, and my pricing and processes are all over the place.”

Running the business is complex. The calendar is dense with meetings and deadlines. There’s no sense of spaciousness and no end in sight.

It’s hard to get out of this situation of feeling stuck and resenting your business until you get a signal again, so to speak, and have a fixed destination.

The distant mountain metaphor from Neil Gaiman’s 2012 commencement speech, “Make Good Art,” has helped me and the many freelancers I’ve coached:

“Something that worked for me was imagining that where I wanted to be – an author, primarily of fiction, making good books, making good comics and supporting myself through my words – was a mountain. A distant mountain. My goal. And I knew that as long as I kept walking towards the mountain I would be all right. And when I truly was not sure what to do, I could stop, and think about whether it was taking me towards or away from the mountain. I said no to editorial jobs on magazines, proper jobs that would have paid proper money because I knew that, attractive though they were, for me they would have been walking away from the mountain. And if those job offers had come along earlier I might have taken them, because they still would have been closer to the mountain than I was at the time.” (bold mine)

What is your distant mountain?

A senior copywriter named Zach described the contours of his Distant Mountain to me:

• Take weekends off
• Do less admin work
• Make $6,800 a month in pre-tax income
• Bill no more than 5 hours a day, 20 hours a week
• Take off a full day each week to provide childcare
• Find the balance between consistency and some structured flexibility

Maybe your distant mountain is still indistinct, more hazy blue than clearly defined pines, saddles, and rockslides.

Rest assured, you can still avoid detours and time wasted on wandering while you gain clarity.

Answer these three questions

Better questions lead to better insights. These three will help you find the path out of the woods:

Question #1 – What is most important right now in your work?

Question #2 – What do you want next with your freelancing and consulting business?

Question #3 – If you were to earn 20% more, what difference would that make in your life?

Notice how small these questions are and how attainable, the answers.

Most creatives I know simply don’t have some audacious 30-year vision. I certainly don’t.

Elon Musk may want to found the first fully AI-powered content agency on Mars, but I’m satisfied with building a writing cabin in my backyard on Earth. I want to build a portfolio of cash-flowing assets so that I’m less dependent on service work (that is, trading time for money). I want to spend more time writing fiction, even if it’s terrible. I want to travel the world with my family, give to our church and other people and causes we care about, and perfect my smoked brisket.

You know, the basics…

To navigate, you don’t have to know what you want forever with your freelance business. You can start with what you want next.

For me, lost in the Newmarket suburbs, the very next goal was making it back to my hotel room. For you, the very next goal may be writing down all of your ideas and picking the next three experiments you’ll finish in the next “semester” so that you can feature them in your career portfolio. Be sure to read this post, too: “6 Tools for Moving Forward with Confidence Even If You Don’t Know What You Want.”

Right now, are you wandering, which can be pleasurable, or are you lost, which can ruin an otherwise gorgeous sunrise?

If you’re lost, what needs the most attention right now, your map, direction, or destination?

Whip out ye olde journal and answer those 3 questions today. You may discover you’re already headed in the right direction and simply need more patience.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make 6 figures as a freelancer.
3. 1:1 Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign (Group Coaching). Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.