3 Anti-Fragility Goals for Freelancers

Of late, I’ve been thinking about how much uncertainty freelancers face, both as a normal job hazard and in the current geopolitical, economic, and technological environment. Things are crazy.

Certainty is a fool’s errand under the best of circumstances. We know that, and yet we’ll wish that freelancing and life were more predictable, familiar, and comfortable.

I see in myself a tendency to daydream and dawdle and have dalliances with regret when I should be reminding myself, “What’s done is done” and preparing and positioning myself to capitalize on what is.

Take AI, for example. Can we go back the way we came or is that way closed off forever? The mustard’s not going back in the bottle, friends, so the question is, how do you and I adapt and make ourselves and our businesses anti-fragile instead of bemoaning what AI is doing to knowledge workers, including freelancers?

Rumination isn’t strategy. Griping is cathartic but otherwise fruitless.

What is strategic?

Building core competency with the best tools available to you and picking up anti-fragility as a value, mindset, and compass.

With that in mind, I’ve got 3 anti-fragility goals for you.

But first, a silly thought exercise.

Imagine that your feet could grow and shrink independently.

On a Sunday night, both feet are the same. However, the next morning, due to circumstances beyond your control, your right foot has tripled in size to circus clown or NBA player proportions.

Our freelance earning and spending are those bewitched, mismatched feet, and countless factors can cause either one to suddenly grow or contract:

• Changes in spending, and therefore the income you need to bring in, can be temporary, such as saving for a once-in-a-lifetime trip to Iceland or flying home because your dad’s in the hospital.
• They can be permanent, not to mention quite loud, hungry, and poopy: “We just had a baby.”
• Changes can be predictable and manageable, like with the software engineer who told me over lunch that he wanted to propose to his girlfriend. He needed six months to save for the ring, and he planned to pursue more freelance work so that he could save aggressively.
• They can come out of left field. One of my coaching clients sent me this message on a Thursday in March: “Been a tough week here - lost two clients out of the blue. Taking 10 deep breaths and trying to see this as an opportunity.”

No matter how painstaking your planning is or how careful your calculations, variability in your earning and volatility in your spending come with the small business and freelance territory. You will end up in situations and with expenses you didn’t predict.

An early client of mine, someone I had counted as a friend, once told me after I had already finished a project that she was “canceling” it. I could keep the project deposit, she said, but wasn’t going to pay the project balance.

Say what?! I definitely didn’t see that one coming, especially from someone I had considered a friend.

The only predictable thing in freelance (and life and cliché metaphors) is curveballs, and the only predictable solution, if you want to call it that, is three pieces of common-sense advice that I could more accurately call goals:

1. Scrape and scrimp until you’ve got at least one month’s worth of living expenses saved in an emergency or rainy day fund.

A guy who talks too fast and laughs too loud at your jokes tells you, “We need it by Thursday, and we can’t pay a lot.” Because your bank account is lower than a contortionist playing Limbo, you ignore your spidey sense and reach for wishful thinking: “Maybe they won’t have tons of changes. Maybe I can make this budget work.”

Against your better judgment, you put on a brittle smile and tell the client, “Let’s do it.”

Later, when it turns out the client’s mom was an English teacher and suddenly he’s an expert in English prose style and has nothing better to do on a Saturday than blow up your immaculate GDoc with suggested revisions (90% of which would make the content worse, of course), you must admit your miscalculation. Again.

When freelancers are really desperate for income, we find it really difficult to walk away from bad-fit clients.

Having a bit more in savings will position you to say, “I’d like to work with you, but for a project with this scope, I charge $XXXX and need X turnaround time to do work I’m proud of. If you’re not able to swing that, I totally understand. Maybe we’ll have a chance to work together in the future.”

Cash reserves represent walkaway power.

The best negotiators don’t need the deal, and if you know you’ll be okay without that potential client who’s already making you uneasy, you’ll make more strategic definitely-not-earning decisions your future self will smile back on.

Once you’ve got one month’s worth of living expenses saved, move the target to three months’ worth. Then, six. Savings enhances judgment.

2. Never spend less than 30 minutes a day on marketing and prospecting.

You can convince yourself that you’re too busy for marketing, but you’re wrong. You can convince yourself there won’t be consequences down the road, but you’re wrong.

You can make all sorts of excuses for yourself:

• “I’m just not good at putting myself out there.”
• “If I just keep my head down and do good work, everything will work out alright in the end.”
• “Marketing feels intimidating, overwhelming, and often kind of gross, like ‘Look at me! I’m desperate for attention!’”

Take it from a industrial-strength excuse manufacturer like me, you literally can’t afford to let your pipeline go dry, and even if you’ve never really needed to market yourself because you’ve always done just fine with referrals, you’re still abdicating a core business competency. To learn how to be good enough at starting conversations and generating leads can only serve you, no matter where your work and career take you.

If you give marketing its rightful place at the top of your daily to-do list, you will figure out how to meet your commitments to clients in the time leftover.

3. Keep fiddling with your prices and offers until you’re able to make what you need to make in 20 to 25 billable hours every week.

In my experience, it’s just not realistic to bill for 35-40 hours per week, week after week, month after month, with unfailing energy and no unwanted health or life surprises.

The better, more realistic strategy is ratcheting up your efficiency and effective hourly rate bit by bit (what you actually make per hour, whether your charge hourly or not) until you can generate the gross revenue your business needs to pay you the net income you want in 20-25 hours of client work each week.

That will leave you with plenty of time to run the business (e.g., marketing, admin, project management) and work on it (e.g., strategy, planning, business development).

Many freelancers work too much because they don’t have efficient, well-defined systems and processes, and because they don’t charge enough. Undercharging results in working more hours to hit the same revenue target. More hours spent on client work leaves fewer for marketing and growing the business with high-value leads.

You get trapped in a underearn-overwork cycle.

Control what you can.

No matter how diligent or disciplined we are, we end up in situations we couldn’t anticipate. Your earning will fluctuate. Your expenses will jump the fence and terrorize the neighborhood cats before ending up at an animal shelter one state over. On your birthday.

Without a crystal ball, you’ll never have perfect prevention, but you can set goals that dramatically improve your preparation and positioning.

Are you well positioned to quickly respond to and even benefit from changes in the market?

Which game are you playing, wait-and-see or act-and-adapt?

The one constant in business is change, so my friends, design a game you can win and control what you can.

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.