One Overlooked Advantage for Freelancers and Consultants - Figuring Out What You Want

This post has a single aim: to convince you that people who know what they want have an advantage over people who don’t.

I’m fond of advantages. If I need to drive a nail, I’d rather have a hammer than a rock. Wouldn’t you?

Knowing what you want and what you want your life to look like is a crucial, often overlooked force multiplier for freelancers, consultants, and solopreneurs. The clarity enables you to quickly sift opportunities, seek the ones that align with your destination, and waste less time on the dead-ends and detours.

Strategic wayfinding is some of the most important work you can do, and I’ll share an exercise for determining your destination, even if you struggle to articulate what you want (in part because you want so many things).

Here’s what you’ll learn:

• Why money makes a crappy compass
• The importance of determining a “clear enough” destination
• Reasons it’s difficult for many of us to articulate what we want
• The distant mountain exercise that I use with coaching clients
• How to navigate if you can’t decide what you want next

Why does money make a crappy compass?

A clear picture of the future isn’t the norm for most freelancers. I’m speaking from personal experience here.

The driving force behind many of my decisions for most of my adult life was paying off debt. How I accumulated debt in grad school, in the early years of my marriage, and through various business ventures is a nap-inducing tale for another time. The gist is that I didn’t want debt hanging over my head.

Without fully realizing it, I’d come to believe that getting rid of debt would enable me to live the life I wanted. Debt takes an emotional toll, and by eliminating it and having more income free rather than always already tied to debt service, I would have more options, more freedom, and more joy.

When in doubt, choose the option that leaves you with the most options, right? Right, and the problem with money-focused goals, including becoming debt free, is that money symbolizes something else we want: a sense of safety and stability, more time spent in an art studio, or taking a year to travel the world.

Money isn’t the point. Money isn’t the destination so much as a sign pointing elsewhere. You can find millions of contented people with very little money, and millions of miserable people with more money than they know what to do with.

For most of us, money signifies something vague like “desired lifestyle.” One of the best ways to add more bullet points and details is to ask yourself this question: “If money were no object, how would I spend my time?”

Many entrepreneurs, consultants and freelance creatives included, can’t produce a clear, satisfying, and actionable answer to that question, so we default to “make more money” as the forcing function in our lives and businesses. Surely, we can outearn our existential angst. Surely, the fog will lift once we reach a certain income bracket, and the purpose of life, the purpose of your life, will become clear as a dime-sized wart on your nose.

I wanted debt out of my life. Period. I maximized my earning at every turn, and when I finally kick the $113,603 in doubt out of my life, the landscape before didn’t suddenly resolve into a rolling parkland and orchards. The effervescent joy I had expected didn’t bubble up and transform me in a flash to the jolly, dancing Mr. Fezziwig from Charles Dickens’s A Christmas Carol.

Certainly, I felt a weight lift from my shoulders, but beyond the mental relief of knowing I didn’t have to push myself so hard all the time, I felt a strange, disorienting blankness, that is, not much of anything.

Reaching the top of the Debt Free climb showed me that it was a false summit. The journey toward my “rich life,” to borrow a phrase from Ramit Sethi, had only begun.

Why is it important to have a “clear enough” destination?

Perhaps you’re one of those solopreneurs who does know where you want to be in three years. I salute you! However, if you’re not the person whose friends envy your clarity and commitment, then that reflection on misplaced hope persuaded you to look beyond money goals: What does money represents for you?

Entrepreneurship in general and the freelance and consulting path in particular have much in common with a forest, only unlike two hikers headed to a scenic overlook, two freelancers may want to end up two different places.

For example, check out what consultant Wairimu and copywriter Zane told me they wanted:

Each of us must, must, must determine a clear enough destination. Destination determines direction, and direction determines strategy. By lining up a destination, direction, and strategy now, we can avoid tortuous (and torturous) wandering and the wasted effort and disappointment it brings.

Why is it difficult for so many of us to articulate what we want?

Now we arrive at the root of the wayfinding problem. Many of us walk in circles because we haven’t yet articulated what we want. Let me summarize that struggle:

• Solopreneurs have interests, desires, and dreams all over the map.
• As I established, money is neither a reliable compass nor real destination.
• Achieving milestones doesn’t feel like we expected or bring the desired clarity, a phenomenon so common that psychologists call it “arrival fallacy.”
• Family, peers, vanity, and culture at large tell us what we should want, and that cacophony of voices and opinions often contradicts and obscures the true desires buried in our hearts beneath fears, “shoulds,” and other people’s expectations.
• Meanwhile, we’ve still got to find work, pay our bills, and navigate the business landscape, ideally in a way that feels like progress.

In an interview, performance coach Todd Herman explained why so many of us feel stuck and discontent: “The reason that many people would have levels of dissatisfaction or they aren’t maybe taking the inspired action that they’re supposed to be taking is because it’s not what they actually want.”

What’s a beautiful, multipassionate, multipotentialite freelancer to do?

Why, figure out what you want!

I’ll explain the distant mountain exercise that was so clarifying and galvanizing to me that I now require all my Business Redesign coaching clients to adopt them. (Otherwise, they won’t have the focus required for the transformation and exciting outcomes.)

What’s the exercise I give to my coaching clients?

Though no one comes right out and says it, freelancers and other creative entrepreneurs experience inertia precisely because we think we’ve got to have  some kind of plan to make a dent in the universe and make your grandmother proud.

The truth is, we don’t need to feel pressure to be anything but our beautifully ordinary selves—no dented universe required—and the most helpful analogy I’ve found for thinking about this more common, and dare I say saner, variety of solopreneurship came from author Neil Gaiman’s 2012 commencement speech, “Make Good Art.”

He paints a picture of a distant mountain:

"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."[5]

Marking your distant mountain isn’t deciding what you want to do or where you want to be forever. Instead, you pursue a minimum energizing clarity about what you want your life to look like in three years.

As Cameron Herold notes in his book Vivid Vision, three years out offers “the perfect balance between realistic and achievable.”

The goal is a written, precise, unambiguous picture of what your life and the business looks like three years from now.

Someone who is thinking three years out will notice and take advantage of opportunities aligned with their vision. You let your future be your filter by creating a written, precise, unambiguous picture of what your life and the company looks like three years from now.

What do you want your life to look like in three years?

Describe each of these in 3-4 bullet points:

• Guiding Values
• Work & Business
• Finances (Earning, Saving and/or Giving)
• Passion Projects / Creative Practice (e.g., Writing)
• Relationships (e.g., Friends, Family, Romantic)
• Service
• Travel / Fun / Adventure
• Spirituality
• Physical & Emotional Health
• Learning

The bullet points will act as an outline for the first draft of your distant mountain, and once you have bullet points, flesh them out with more language and detail. Polish it. Put more consideration into word choice. You’ll end up with three or four pages.

Focus on What will be true, not How you're going to get there. Pretend that you're describing your dream home to an architect. Leave out numbers and data for now.

What if you still don’t know what you want next?

From time to time, I share the distant mountain exercise with a freelancer, consultant, or solopreneur, and I see a panicked look in their eye. When I press them, they admit that they don’t know what they want. That’s not always bad. Sometimes, they’re quite content because they have enough. They’re feeling not exactly lazy but a demotivating fulfillment. Goals don’t drive them.

If that describes you, I recommend that you take hold of one principle and also define your non-negotiables.

The principle is one I already alluded to: Pursue the opportunities that leave you the most options.

• If one prospect insists that you meet in person and another says Zoom is fine, pick the one who doesn’t mind Zoom. That way, you’re free to work from anywhere. You’ve kept your options open.
• If you have to pick between a new client who lets you work asynchronously and one who expects you to attend several meetings each week, go with the one who leaves your calendar clear. You have more options that way.
• If you don’t really need the money and you can pick between a lower-paying project that can become the crown jewel of your portfolio and a higher paying project that you’d never want to share, go with the lower-paying project. A stronger portfolio creates more options for you.

Those of you who want to go deeper with this concept can check out this post on preserving optionality.

Next, define your non-negotiables. Here are examples in no particular order:

• Location Independence
• Calendar Autonomy
• Excellence
• Value-Conscious Clients
• Low-Meeting, Async Workflow
• Sense of Humor (or No Dice)
• Humility > Ego

Notice that some of these non-negotiables may be your guiding values (for example, excellence and humility), others are attributes of your desired lifestyle (for example, location independence), and others are traits of attractive client relationships or opportunities (for example, the client is value-conscious, enjoys humor, and avoids unnecessary meetings).

In the absence of a clear vision for your life, use non-negotiables and preserved optionality to navigate. You’ll waste less time and effort on ill-fitting relationships and dead-end opportunities.

Let’s end where we started.

People who know what they want have an advantage over people who don’t.

If you want to go through a formal wayfinding process, check out my Business Redesign group coaching program. It will help you raise your rates, delegate with confidence, and free up 40 hours a month as you begin implementing the $300K Flywheel framework. Wayfinding is the first month-long “sprint.”

To be considered, apply here.

When you’re ready, here are 3 ways I can help you:

1. Freelance Fixes. This short guide walks you through 6 small but important “fixes” that you can make to raise your income without working longer hours. People really seem to like it.
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. 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.