Five Tough Lessons These Solopreneurs Learned In Their First 12 Months

One first-time independent worker says his first year in business was a “trough of sorrow” because he grossly undercharged.

Five Tough Lessons These Solopreneurs Learned In Their First 12 Months
[Photo: Simon Potter/iStock]

When you start working for yourself full-time, it’s like taking a crash course in business ownership–but with no instructor and extremely high stakes. But if you can get past the one-year mark and still see a path ahead, it’s likely because you’ve learned from the inevitable pitfalls of going in blind. Here’s what five independents who’ve just finished their first year as “solopreneurs” said their biggest blunders taught them.


1. Trying To Do Too Much Too Soon

Stosh Walsh started working for himself as an organizational development consultant the way most first-time consultants do–by tapping his professional network. Things started off strong. An all-or-nothing kind of guy, Stosh felt encouraged by a steady stream of income. So he build a product in an adjacent market while continuing to volunteer on the side.

But contracts, proposals, and the sales cycle were foreign to him and took longer to wade through than he’d expected. And before long, he was running into delays with his product; collaborating with outside partners was a slow process. Hitting the ground running soon felt more like wading through quicksand. “You’re up to your ankles, and you’re moving, but soon it’s up to your knees,” Walsh says. “You realize you’re soon not going to be able to move.”

Then, eight months in, he got shingles. While his mind wanted to push forward, his body wouldn’t cooperate. Walsh had to slow down–and he’s grateful he did. These days he’s still offering services and is building his product, but he isn’t burning himself out in the process.


Lesson learned: “Everything takes longer than you think,” says Walsh. “Hold your plans loosely. So much will change.”

2. Not Planning For Slow Stretches

After leaving her job as the VP of digital strategy for a respected advertising firm in New York, Sharon Panelo quickly built her business by networking. But like most first-time independent workers, she struggled with an inconsistent income in her first year of working for herself.

During one particularly slow stretch, on her couch in her sweats, Panelo read ads promising her a $1,000 windfall basically overnight. She’d already invested in a pricey graduate degree from Columbia, but she was still intrigued and spent another $4,000 in educational courses. Those investments didn’t pay off. Panelo realizes now that the anxiety of her first major income slowdown got the better of her. She had extremely marketable skills all along–she just needed to market herself better to smooth out the ebb and flow of her business.

Lesson learned: Expect slow times and think ahead. Instead of feeling vulnerable and taking random actions, you’ll face this rough period with a plan.

3. Undercharging

Programmer Karl Weber went independent out of necessity during his wife’s difficult pregnancy, which required his presence. He started his business with an existing client, and while it paid way under market value, the work kept him afloat without burning through their 401(k).


Looking back, Karl calls his first year a “trough of sorrow,” mostly because he charged too little. Since he wasn’t making enough money, he started doubling up on projects to bring in extra cash, but then he’d be overworked and miss deadlines. Things got so bad he was almost evicted a couple of times. Finally, he changed his rates.

Weber feared he’d drive clients away, but one actually gave him a bonus at the end of the project, and another told him point-blank to charge more. He ended up doubling his rates–twice–during his first year, bringing him more in line with his local market, at $50 an hour.

Lesson learned: “Charge a livable wage–it’s at least double what you think it is,” says Weber.

4. Not Saying “No” Enough

Though she’d saved nearly five months of living expenses and had six months of guaranteed work, personal finance writer Cait Flanders still worried she’d run out of money. That scarcity mind-set made her hesitate to say “no” even once. So Flanders accepted every offer she received and ended up working more in her first six months than she did when she was juggling a full-time job and freelance work on the side.

She started dreading work and resenting her clients and turning away her friends. She felt like she couldn’t take a break. She didn’t go outside and gained weight. It took about six months before Flanders finally realized she needed to make a change. She started scheduling a weekly day of adventure and said no to extra work from current clients. Her bank account is just fine.


Lesson learned: Trust your gut when it comes to accepting work from clients. If you really don’t want to do the work, don’t do it. You’ll be happier, and the client will be happier going with a different freelancer.

5. Mismanaging Time

Copyrighter and designer Beth Bogdewiecz went solo when she realized that money was one thing but time was something she could never get back. “Clocking in and out and face-time is such an antiquated way to work,” she says. But as her own boss, time management didn’t come as easily as she’d hoped.

Like many first-time independent workers, Bogdewiecz wasn’t used to not having an office to go to or someone telling her what do. She didn’t know how to prioritize or structure her schedule. And it wasn’t just about when she worked, but when she didn’t work. Bogdewiecz worried about losing a client if she didn’t meet their time demands.

It finally came to a head when she was set to take a 10-day vacation and began to pack her laptop. She stopped herself, realizing it was ridiculous–she needed a vacation. Bogdewiecz went off the grid the whole time and didn’t answer a single email. She didn’t lose a single client, either.

Lesson learned: You’re in charge of your business. Set a schedule that works for you.