The Tao of Freelancing

Learning to embrace your strengths and accept your weaknesses

If you want to learn how to be a happier, more prosperous freelancer your best bet is to read Benjamin Hoff’s The Tao of Pooh. Hoff uses A.A. Milne’s beloved stuffed bear to explain the concepts of Taoism is a way that is approachable, understandable, and irresistible.

Taoism may seem like a strange philosophy for anyone working as a freelancer. The primary ethos of most freelancers is to struggle bitterly or to hustle incessantly. Taoism is more focused on the journey than the results. One of the major tenets of this Eastern philosophy is wu wei. Wu wei is a Chinese phrase. It signifies the concept of not taking action or of not forcing anything.

How can not taking action help you build anything? Isn’t wu wei and Taoism in direct conflict with my oft-repeated advice to work hard?

Stop Fighting the Current

I’m not suggesting that you should give up working and experimenting. You don’t need to become a Taoist monk to enjoy a fulfilling career as a freelancer.

But, you do need to give up a certain amount of ego. You do need to let go of certain practices that are harmful to your personal development and growth as an individual.

You need to learn when to fall into the flow of the current instead of fighting to get upstream.

We each have our strengths and weaknesses. Our modern culture emphasizes eliminating our weaknesses. Many of us internalize the idea and think that anything we have to struggle for is more valuable or more authentic than something that comes easily for us.

As freelancers, we may spend hours focusing on trying to root out our weaknesses to prove we have the stuff to be successful. Instead of letting our freelance business take us in the direction of our natural strengths and interests, we fight as hard as we can to build the kind of business we think we are supposed to be building.

But, often all of that struggle leads to frustration and burnout instead of contentment and success.

The truth is that by the time we become adults our character has already hardened. That doesn’t mean we cannot change. But, it does mean that big changes take a long time. When we try and change our character through the blunt force trauma of rigid goals and self-shaming we hurt our confidence, our weaknesses remain, and worst of all, we erode our strengths.

Think of the way a river changes the canyon. It cuts through rock with its small, consistent flow over the course of eons.

If you have set New Year’s resolutions, chances are you are already falling behind. You need to allow change to be a gradual process to improve your chances of making it last.

Finding the Tao of freelancing is about allowing yourself to be flawed and letting your strengths guide your journey.

Letting Your Strengths Guide You

I am not detailed oriented. One of my law school professors once told me that I was more gifted than most at seeing the forest, but that I had no patience for examining the trees. I spent years trying to become more detailed oriented. I failed.

My biggest business failure was because I was not detailed oriented enough. I allowed myself to be vulnerable to unscrupulous employees and business partners.

I am also not a good manager of people. I just want people to figure out what they need to do and to figure out how to do it. I’m happy to answer questions, but I hate giving directives.

I work best as a solo professional. I am confident that I have the marketing skills to build an agency. I am equally confident I lack the personality to enjoy operating an agency, and I lack the management skills to sustain an agency.

I am good at finding new angles on “boring topics”. I excel and making complex topics interesting and understandable. When I have pursued freelancing projects that required my strengths, I have done better work and made more money.

I spent the first two years of my freelance career angry and frustrated with clients and my business. The problem was I wasn’t letting my strengths guide me to the work I was best suited for. I was too busy hustling to find anything I could.

I thought that through hustle and being proactive I would find enough work to support myself. I didn’t understand the mental toll working for the wrong kinds of clients would take. I was struggling to paddle upstream against my own nature. I almost drowned.

Once I consciously decided to do the kind of work that came easy for me, freelancing become fun.

It also became a lot more profitable.

Paddling downstream gets you farther faster than paddling upstream.

Let Go of Ego and Hurt Feelings

The other tenant of Taoism that is critical to freelancers is pu. Pu is a Chinese word that means unworked wood. It’s a metaphor for keeping things simple and accepting things as you find them.

Clients love to be right. Even when they have hired you to be a subject matter expert, they want to be right. One way to enjoy your work more is to allow them to feel that they are right. I don’t argue with clients. I either adapt to what they want, or I part ways. It’s not worth the struggle to argue with them.

I once created a lengthy lead magnet for a client. I used title case for the title and subheadings. The client sent me 31 separate emails for corrections they wanted — most of the emails related to not all the words of a title being capitalized. They wanted every “to”, “the”, and “with” capitalized. They questioned my knowledge and skills.

I knew I was right about how to use title case. I also knew that they wanted the titles a certain way. It was their lead magnet. I let go of my ego and made the changes. The client loved my work and has referred many others to me over the years. If I had argued with the client, I would still have had to make the changes, and I may have harmed the relationship.

I once had a client that wanted to change the scope of the project after I had already started. I explained I would have to charge more for the extra work and they would need to pay the extra money right away. They refused. I quit and refunded the money, minus the fee for the work I had already completed. The client was angry, I was relieved. Continuing that relationship would have made be bitter and resentful.

I hate arguing about money. I don’t negotiate my prices, and I require that clients pay me up front. Sometimes I lose out on work because clients don’t want to work that way. If I give in to my panic about not losing a client and give-in to client demands around money, I always make myself unhappy, and those relationships never last.

I have to let go of my fear and trust that there are enough clients that are willing to work with me on my terms. It’s a much less stressful way to work.

Your job as a freelancer isn’t to change client’s minds or the change the marketplace. Your job is to find how your skills fit with what clients and the marketplace need.

Backlash to the Gig Economy

There is a lot of backlash to the gig economy. It’s understandable. Unethical people and businesses are plentiful. But, as freelancers, we have control over who we work for. If we see ourselves as independent businesses, untethered by traditional workplace rules, we can create meaningful and profitable relationships.

Much of the frustration with freelancing comes from freelancers who refuse to let go of outdated ways of thinking and interacting with clients. If you embrace the Taoism of freelancing, you will see that bad clients exist and that you don’t have to work for them.

If you get clear on what kinds of clients you want to work with and what kinds of skills you have that they need, you will find each other. But, you won’t have room for the good clients if you continue to hold onto the bad.

Taoism isn’t about giving up your sense of agency. It isn’t about letting the mystic forces of the Universe take over.

The Tao of freelancing is about letting go of your ego, your preconceptions, and your need to overcome negativity. You have to choose to let go and to trust in your own strengths and instincts.

The next time you have the urge to read a book about freelancing, get a copy of the Tao of Pooh. It may help you see obstacles in your business you have never noticed before.

Written by

👽🌊 Amature Human, Haiku Poet, Pocket Story Writer and Essayist. FREE dailyish newsletter

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store