The 5 Biggest Challenges in the YouEconomy and How to Face Them


Article by Michael Pietrzak

Congratulations, you’ve escaped the 9-5 to become a solopreneur! You’ve decided to join the YouEconomy, the growing global movement of pioneers who have opted out of being told what to work on and when by bosses who also wonder who set up this antiquated, industrial, consumption-obsessed economy.

Will you write cheeky marketing copy for clients on Put your graphic design talents to work on Fiverr? Maybe you’ll start your own business selling ’80s video game memorabilia online.

What will be your biggest challenge? Finding clients? Choosing the perfect coworking space?

If only it were that simple. As you read the following answer, it’ll be helpful to picture it in 300-foot-high flaming letters across a mountainside: It’s you. You will be your own biggest challenge.

The greatest barrier to becoming your own boss is nothing external — it’s the battle for control over the moist computer between your ears.

Lego Despair

I know all of this from experience.

In my 20s, I took a seven-month backpacking trip through Africa. After that life-changing experience, I wondered how I could ever go back to my work in government. Instead, I decided I would dedicated my life to creating carbon-neutral homes with better insulation, solar panels — all the green stuff.

My mom was thrilled I had moved into her basement. For two weeks, I was ultra-productive: I wrote a business plan, connected with builders, and worked on a company logo. But as the weeks passed, I spent more and more time below ground playing Fallout 3, procrastinating, and ignoring my vicious mental chatter.

One Friday morning, I found my old Lego train set and thought it would be pleasantly nostalgic to snap it together. I finished, stood back, and despaired.

I was 26, but I felt like a 10-year-old. What was I doing with my life? I was out of money, living in my mom’s basement, and saw no hope for my business. Terror set in. Back to government I went.

It took me five tries, four businesses, and 10 years to escape into the YouEconomy. Over that time, I’ve become familiar with every form of self-doubt and have learned how to get out of my own way. Here are the five biggest challenges to making it on your own — and how to face them:

1. Self-Motivation

“The best motivation is self-motivation. The guy says, ‘I wish someone would come by and turn me on.’ What if they don’t show up? You’ve got to have a better plan for your life.” — Jim Rohn

Those entering the YouEconomy for the first time won’t understand the challenge of self-motivating. From the day we’re born, we’re told what to do and when. In kindergarten, “Now it’s time to paint.” Catch the bus at 8 a.m. Take this test. Graduate. Go to college and take the required courses. Go straight to your first job and work defined hours on specific tasks handed down from on high.

When you become your own boss, your first question will be, “What do I do now?” You’ll look around, and for the first time in your life, you’ll find nobody there to tell you what to do.

You’re now the CEO of a corporation of one. Not only are you responsible for setting a strategy, finding clients, and managing cash flow, but you also have to keep the entire company motivated and morale high.

How to Face It

Losing your motivation (easily and often) in the YouEconomy is a guarantee. The best way to keep moving forward is to create a vivid and emotional mental picture of your why and conjure it daily. It may be adequate to fire yourself up about how unhappy you were in your old job and how much you never want to go back.

That said, I’d recommend creating a clear, positive picture that includes how you’re using your freedom, whom you’re serving, the stupid amounts of money you’re making, and what this new life allows you to do. Then, pump yourself up until your desire for that life is a 10 out of 10.

Put on pants, daily.

2. Money Panic

“Worrying is praying for stuff you don’t want.” — Jen Sincero

The day you quit your job will be pure happiness and excitement. Your first episode of money panic will arrive when you look at your bank account three weeks later and try to estimate how many months’ worth of food and rent you have left.

If you’re not adept at controlling your mind, this state of panic can become a default anxiety, always on your shoulder. It will impair your ability to do good work and make smart decisions.

How to Face It

Before you jump ship at your old job, write down the dollar amount you need every month to survive. Decide how many months of runway you’ll need to get your solo endeavor to a place where you’re making enough income to survive. Then, double it (expect the unexpected). This is the amount of money you need to save before you quit.

Lock down some consulting work that can help you pay the bills — even if that “consulting” is a few bartending shifts per week. During my last 9-5 job, I secured consistent work in the gig economy that paid my rent and then some. It gave me the security I needed to give the money panic the boot.

3. I’m Not Good Enough

“Most people overestimate what they’re going to do in a year, and they underestimate what they can do in a decade or two or three or four.” — Tony Robbins

As you start off in the YouEconomy, you’ll probably be terrible at whatever you choose to do. Do you remember how long it took you to feel confident in your current role? Now, imagine starting a new job while also trying to do every other job in the company —  bookkeeping, sales and marketing, web and graphic design, video editing, customer support, etc.

When you leave a job you’re good at to pursue several new roles all rolled up into one, it becomes easy to start questioning your worth as a human.

How to Face It

Uncouple your worth as a person from your level productivity or success. I still struggle with this, but I try remind myself: Do you love your nieces and nephews any less because they aren’t yet good at things? Would you love your wife less if she were in a car accident and spent six months in the hospital, unable to work? Why love myself any less when I struggle?

Grow your patience muscle. “Dealing with the temporary frustration of not making progress is an integral part of the path toward excellence,” fitness expert Christopher Sommer once told Tim Ferriss. “[Q]uality long-term results require quality long-term focus. No emotion. No drama. No beating yourself up over small bumps in the road. Learn to enjoy and appreciate the process.”

Show up. Do the work. Results will follow, but on their own timelines.

4. I Need to Push Myself Harder

“Ours is a culture where we wear our ability to get by on very little sleep as a kind of badge of honor that symbolizes work ethic, or toughness, or some other virtue — but really, it’s a total profound failure of priorities and of self-respect.” — Maria Popova

Early in my journey into solopreneurship, I chose a new computer desktop background. It was an image of one of the D-Day landings, shot from the boats, soldiers storming the beach and taking fire. The caption above the image read, “Harden the F*** Up.” I thought this constant kick in the pants would help. If I wanted to make it, I’d need to toughen up.

Forcing myself to live under this guillotine blade only created depression and anxiety, feelings of worthlessness, and disdain for my work. It led me straight to burnout.

I didn’t need to harden up; I needed to balance! When you go to the gym, you work near your limits, not so hard that you pull a ligament. Throttle down.

How to Face It

Protect your most important asset: yourself. If you owned a factory, you wouldn’t attack your employees, you’d praise them. You wouldn’t kick the machines to work faster, you’d maintain them regularly. When your mental and emotional states are balanced and healthy, you do your best work. Creativity flows and your relationships improve, which are all-important in any business.

Leave something in the tank. This actually makes you more productive. Hemingway would stop writing only when he knew what would happen next. That way, he would know exactly where to start the next day (and could be drinking wine by noon). He knew to stop before the writing became a chore.

5. Not Having an Off Button

“To every thing there is a season, and a time to every purpose under the heaven.” — Ecclesiastes 3:1

As your own boss, you will be tempted to work at every waking moment. Early in my journey, my official working hours were 8 a.m. to 6 p.m., but I often found myself responding to emails, making minor tweaks to my website, and reading marketing blogs into the night while watching TV.

This half-there work is counterproductive on two counts. First, anything you do while multitasking will deliver lower-quality results. Second, you need absolute downtime to unplug completely to keep yourself sharp and do great work.

How to Face It

Schedule downtime. There is a time for work and a time for effort. Use the “unschedule” to protect your time for play, exercise, friends, and inactivity.

Take a tech vacation. Put your phone in a drawer and power down your laptop. If you’re not disciplined enough to stay away, use apps to block your access to certain sites, apps, or the internet. I’ve heard good things about Freedom.

Lastly, remember why you are working in the YouEconomy in the first place: to set your own schedule and work on what you want when you want, to love your life, and to feel joy most of the time. Blow off work once in a while. Enjoy your freedom and you might just find your footing here in the new world of the YouEconomy.

A version of this article originally appeared on

Michael Pietrzak is the founder of So You Want to Write? Inc., which helps writers improve their writing and get published. He’s passionate about personal development, CrossFit, and playing guitar.

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