Surviving the first year in business

Note to readers: this post is part of an occasional series about what it’s like to start a business.

Over coffee, an acquaintance told me about his mother, who ran her own freelance writing business for years, then later decided to take on a traditional office job. “It’s the opposite of what you did,” he pointed out, which made me pause. After more than 20 years in a cubicle, this past spring marked my first year as a freelancer. Here’s to doing things backwards! Would I recommend it? See for yourself.

Lunch break at Farragut Square; Washington, DC.

Forget preparation

Face it, you almost never feel ready – for that new project, for a plunge into a new skill you want to try, or even opening up shop in the first place. Sure, do the research if you must. Talk to people, take a class. Just know that none of that really matters. Thinking through a business scenario isn’t even remotely close to living it.

Consider all the different angles, of course, then go ahead and make your decision. Try not to drag it out, and never second-guess yourself. Excellent logic that worked yesterday may not replicate well today. You’ve got to stay flexible and alert all the time.

Realize that whenever you read about someone else’s success, there’s no need to bookmark the article or bother taking notes. Your story is going to be all yours, better to live it than to spend time carefully crafting what you think should happen.

Remember, whether things go right or wrong, at least you’re out there trying.

We can’t predict what will happen tomorrow, but it’s always tempting to try. When you’re freelancing, the uncertain outlook can encourage anxiety. Those overwhelming unknowns keep on multiplying. Where will the next client come from? Will there be a next client? What are quarterly estimated taxes again?

It’s easy for nerves to take up lodging in your left brain, driving your logic to loop through worst-case scenarios. Stay strong. This path you’re following will branch, and then branch again. Be confident in your ability to weather whatever awaits you.

When you’re spinning in circles, are you moving forward?

Sometimes, when you’re freelancing, the day seems like one giant dizzy spell. Keeping clients straight, if you have them; marketing nonstop if you don’t. Maintaining flawless customer service. Running all over the city and suburbs to get to project sites and meetings. Hauling around the laptop that serves as your pop-up office wherever you find WiFi.

Before you get clients, a living wage looks like it might be impossible to ever achieve. After you get clients, your rate is the source of constant internal debate. If a client accepts the terms, you wonder if you should have charged more. When a client disappears, you beat yourself up about getting greedy.

Reject a mercenary mindset. Focus on your business priorities, and not so much on the dollars. As you’re getting started and beyond, building relationships is more important than your bottom line. Hard as it is to believe, the money comes only after you let go of chasing it.

Business as a second language

Immersed in a new freelance environment, most of the time you’re wandering around lost, asking everyone for directions. The problem is, you can’t always understand the response. As for the culture, you find it incomprehensible.

You could sure use a translator, but all you’ve got is your not-very-helpful inner voice. Under stress, that negative self-talk can turn compulsive, assuming the role of defining important business concepts like the definition of “real.” This client isn’t real, because s/he’s a friend of a friend. This project isn’t real, because it’s not something you list under your services.

You don’t need a dictionary to confirm that a check or a bank deposit is real money.

As your freelancing progresses, friends and family can’t take you anywhere without you critiquing other businesses. You shake your head at the restaurant with no posted hours. How can an establishment not care that people are trying to figure out how early or late, or even what day, the place is open? You can’t get over the shop owner who avoids greeting customers and, when she does talk, recites her woes in place of casual conversation. Not to mention the sole proprietor technician who refuses to respond to multiple SOS service calls. From all of these scenarios, you’re learning.

As a business owner, figuring out what not to do is important, too.

Depending on the day, freelancing can seem like a pipe dream. You find your energy as scattered as your projects. Every task on your to-do list takes more effort than it should. That is, until you receive an unsolicited thank you. Then what a welcome shot of renewed enthusiasm.

You wonder why so many people you encounter are argumentative, hard-headed. Keep looking, eventually you’ll run into the incredibly generous ones. A brief encounter with kindness, that’s all it takes to change your outlook.

There are those weeks when you might send out 50 queries before you make one connection. Such odds are pretty daunting. Maybe you even think about giving up freelancing, and finding a traditional, established, accepted 9-5 career. Before you do, consider this: one connection is a start that you can build on.

Creating a business process and seeing it through from start to finish can feel like you’re going in reverse. That is, until it finally works, and a new client reaches out.

Meanwhile, you’ll rack up the mistakes. At the same time, you’ll normalize a constant sensation of being off-balance, and develop incredible resilience. Up for all that?

Then go forth, and get unconventional.

Have you tried a new venture? Share your experience in the comments…