Diary of a web worker: On being a solopreneur

Diary of a Web Worker is a new series where I spill my guts about the realities of running a successful small business. This month, we're all about solopreneurship. In other words, starting and running a business completely on your own. The ups, the downs, practical strategy, all of it. Hang on to your skivvies!

As I sit here fully caffeinated, running on zero hours of sleep in the Starbucks down the street, solopreneurship is heavy on my mind. I've given it up. And if this fails, I cannot, will not go back.

It's not that being on my own was that bad. In fact, for the first few years, I swore I would never hire anyone. With barely any overhead and my ability to do anything and everything to the epitome of perfection (a trait I've since discovered isn't quite as good as it sounds), I was invincible. No economy could blow my umbrella inside-out. I was too nimble for that.

But around March of this year, I started struggling with anxiety in a massive way. My Type-A self has always had a bit of a nervous streak, but until recently I've counted it as an asset. When I am faced with a problem, my ever-ready mind keeps attacking it until it's solved. My fear has given me a sort of edge. I've succeeded where others have failed because my mind just. won't. quit.

But when my general feeling of apprehensive problem-solving turned into the feeling that I'd almost been hit by a car -- 24 hours a day -- I was forced to see my anxiety as it really was. Not as a normal part of my personality, but as something that was killing me. And if I let it, the business that I worked so hard to build.

In the beginning was the girl

By day, I was an event planner at a local university, data entry clone for a yearbook publisher, and editor for a budding author.

2007 was my first year as a solopreneur -- at least, for part of the time. After I quit my full-time corporate job, I took on three part-time jobs that would allow me the flexibility of working from home. By day, I was an event planner at a local university, data entry clone for a yearbook publisher, and editor for a budding author. By night, I designed and developed websites for myself -- each one being God's gift to the internet. I had spent the few years prior to that building up a blog, which I eventually sold, giving me the impression that I had a green thumb for online business.

It took me six months to realize that building a blog with later hopes of selling it was not an effective business plan. It hit me that I needed a product or a service to sell if I wanted to be self-employed any time soon. Enter S.Joy Studios.

The solopreneur that was not

By late 2007, I was fully in business. I quit two of my part-time jobs and worked hard to be seen as a "real" business. I said "we" a lot. I used big words. I had a blog (that no one read) that talked about all of the impressive things "we" were doing. I knew I needed credibility, but I didn't believe in myself enough to make a dent in that department.

Still, people need websites, and I was a good designer. I eeked out a living over the next year and a half, and I started getting really interested in design accomplishing things. Without knowing it, I became a student of web strategy.

In late 2008, I quit my last part-time job. It was the scariest leap I had taken up to that point, but I was so stressed doing both that I knew it had to be the right decision. It was.

By that time, I had dropped the "we". I had come up with an idea for packaging my services that, at the time, no one else was doing.

Packaging your services (v.): The act of coming up with different fixed-rate packages clients can choose from. It makes it easier for people to buy from you, resulting in your calendar being full to over-flowing.

My service packages immediately tripled the number of people who wanted to work with me. I discovered Twitter and met Danielle LaPorte, who was the first person to tell me that I was a genius.

A paradigm shift

Danielle's Fire-Starter Sessions are one-hour sit-downs with Danielle LaPorte, empire-building maven and one of my personal heroes. She nailed what I needed to do to move forward. Ground was broken, epiphanies were had.

In early 2009, I decided to take another leap -- to do a fire starter session with Danielle. It doesn't sound like a big deal to me now, but at the time, I was a card-carrying Boot Strapper. Capitals. I didn't spend money on anything. To pay someone $300 to talk to me for an hour felt like having surgery without being knocked out first. (Note: The price has since gone up.)

My session with Danielle LaPorte was a turning point. Something shifted in my brain. I finally knew what I stood for and what I didn't. My tentative idea for a pre-built design solution came out fully-fledged -- LiteSites grew wings. So many intangible notions took shape that day, most of which I can't even explain. (By the way, I'm not affiliated with Danielle's Fire Starter Sessions in any way. All of this is just my experience.)

Two weeks after our work together, I became booked solid and have been booked to over-flowing ever since. I launched LiteSites last summer, which was an immediate and earth-shattering success. I started planning the gold-digging excursion, which was my tippy-toe into sharing all of my hard-won knowledge via an online multi-media classroom format. Things were very, very good, and I was working very, very hard.

The burst of my solopreneur bubble

I couldn't get on Twitter without this tidal wave of fear swallowing me up.

My flood of anxiety came at the worst possible time -- during the launch for the excursion. I plowed through anyway. I kept on persevering throughout the excursion, which I was incredibly supported by -- such an amazing group of people giving me positive feedback every single day. But by the end of April, I was done.

But I wasn't done. I still had clients. Projects that I was excited about starting. I still had (and still have) stuff from the excursion I needed to wrap up. But I couldn't get out of bed. I couldn't check my email. I couldn't get on Twitter without this tidal wave of fear swallowing me up.


I had lost all of the strength that I was so proud of. My stubborn independence and unwillingness to fail was taunting me. It felt like the whole world was watching me. I could do nothing but lay in my bed and cry buckets.

For a few weeks, the only way I could function was to pray that God would give me the motivation and desire to get out of bed. I would literally say, "I can't do this by myself. I am not getting out of bed unless I get this sudden miraculous desire to do it." Some days, it would really happen. I would lay there for 20 minutes and all of a sudden, my desire would shift, and I would find myself at a coffee shop, happily working away. Other times, that mysterious desire wouldn't come, and I'd sleep until 12 and feel like a horrible person because of it.

Somehow, I started re-gaining my strength and made the decision to hire my first employees. Leah had coded for me in the past and was a dream and a half to work with. Julianne was one of those rare creative firecrackers -- if I was going to have a team, she was going to be on it. And here we are.

What three years of solopreneurship has taught me

Life is different now. I still struggle with anxiety every single day, but I'm working through it with a counselor. My days are different now. The more people I hire, the more people I realize I need to hire.

But I don't regret going at it alone for so long. Solopreneurship was an exciting, rewarding experience. And if I had waited until I had the resources to hire people, I would never have started. Still, if I could go back in time, there are a few things I would tell the younger me.

Dear Sarah,

Don't worry if you're not the best yet. After you've put in 10,000 hours, you will be.

Savour your open calendar. Use it to make your brand and your systems great. Those are the things that are difficult to find time for when you're in high demand.

Forget 9 to 5. Figure out how you work best and use it. Take your weekends. Make them sacred.

Plan for your downtime before you plan for anything else. Take twice as many vacations as you used to.

Don't believe the lie that you are the only person who can do things well in your business. Do what you're best at, and find a way to delegate the other stuff.

Learn how much your time is worth. Knowing that is crucial, whether you sell products or services. (Book Yourself Solid by Michael Port is the best resource for figuring this out, and it needs to remain by your bed for the first six months of your business adventure.)

Always go with your gut instinct when deciding whether to take on a project. Taking on projects that are not true to you will, at best, rob you of your time. At worst, it will rob you of the opportunity to work on the projects you were born to do.

Learn to live in the present. Enjoying the place that you're at right now is one of the keys to combatting fear and discontent. I like to visit themindfulist.com for daily mindfulness prompts.

Find ways to be kind to your solopreneur self. Treat it like a child who you love dearly. Daily rewards are more effective than daily thrashings. Think treats and surprises.

Remember how small you are. The sun does not depend on you to rise. No one's life depends on your performance. And speaking of performance, remember that you are not valuable because of what you do. You are valuable because of who you are. Give yourself permission to be eccentric.

And Sarah, don't forget the little girl who reads too many books and who wants to know everything. She is still you, and she is the best part of you. Don't lose yourself in the process of trying to be great. You already are.

Fondly, Sarah