Two Years of Self-Employment: What I've Learned

Tomorrow marks 2 years since I left my career as a psychotherapist to build WordPress sites full time. In some ways I feel like I could write a book about everything I’ve experienced since then; in other ways, I feel like what I know wouldn’t fill a thimble compared to some of the awesome people I’ve met along the way.

What I do know is this: Self-employment never turns out quite the way you plan, and things can (and will) change at the drop of a hat.

I’m far from an expert on running a business – in fact, most days I still feel like I’m flying by the seat of my pants – but I thought I’d share a few of the lessons I’ve learned the hard way while running a business from home.

Lesson #1: There are no friends in business.

When I started my web design company, I needed a portfolio and I needed one quickly. So I rounded up a bunch of friends who needed websites, charged them next to nothing, and got enough screenshots for my initial portfolio. I will always be grateful to those who took a chance on me in the beginning because I wouldn’t be where I am now without them.

That said, I quickly learned that working with friends is (usually) a bad idea. You feel pressured to give discounts. You feel pressured to do away with things like contracts because this is someone you trust. And then a “friend” stiffs you for hundreds of dollars and you don’t know how you’re going to pay your bills. (Not that I would know from experience or anything.)

What I learned: I still do work for my friends occasionally. But they sign a contract like everyone else, they pay deposits like everyone else, and they don’t get discounts. I love my friends, but I love electricity and food even more. If a friend has a problem with that, I tell them to hire someone else.

Lesson #2: Recurring income is the best thing in the world.

No discussion of self-employment is complete without the phrase “feast or famine” – the phenomenon where (believe it or not) you no longer receive a paycheck via direct deposit every other Friday. In two years, I still haven’t managed to come up with a great system for dealing with this. However, I’ve figured out that it helps when I can expect a certain amount of income each month no matter what’s on my design schedule.

Because of that, my business has morphed to include things like site management, retainer hours for regular clients, training for bloggers and designers, and (eventually) online courses. These offerings allow me to anticipate a certain level of income each month regardless of how many design projects I complete, which means I can establish a baseline for my budget. I can’t stress how important this has been as I continue adjusting to life without regular paydays.

What I learned: A lot of people become self-employed to escape the monotony of trading hours for dollars, only to find that they’re still trading hours for dollars. I know that was/is true for me. Building recurring or semi-passive streams of income is essential if you want to have a life outside your home office.

#3: When things start looking up, it’s time for something to go wrong.

I don’t mean to be an Eeyore, but I’ve noticed that every single time things are running smoothly in my business, some disaster is about to strike. It’s something I’ve just learned to prepare for – when I start getting into a routine and feeling good about the way things are going, I better enjoy it while it lasts.

Last fall I started hosting a few client websites. No big deal, just 4 or 5 people. As word spread, I kept adding more people and slowly expanding until I had just under 200 hosting customers and a couple of colo servers. The income was great, though the time I spent providing support was becoming an issue. I was on the brink of hiring help when a competing web host decided he felt threatened by my business. The next thing I knew, my servers were under a DDoS attack from Asia that lasted 9 days – it stopped as soon as I ran out of money to try mitigating the attacks and announced that I was closing the hosting part of the business.

Not only did that debacle cost me nearly $10k between trying to stop the DDoS attacks (the datacenter said it was one of the heaviest they’d ever seen) and refunding customers, but it also severely damaged my company’s reputation. Customers didn’t understand that I had no control over what was happening; they just knew their sites were down and they were not happy. Had it not been for Jesse Michelsen’s help, I don’t know how I would have gotten everyone moved to other hosts without losing it.

I’ll be honest – that whole event was probably the lowest point I’ve reached since I left my career. I didn’t know whether to go get a real job, rebrand and start over, or join the circus. I felt like a complete and utter failure for letting everyone down. But after taking a month or so to lick my wounds, I was ready to come back and do things differently. And while I would give anything to change the way it went down, I am SO glad I don’t deal with hosting anymore.

What I learned: When you run a business, everything is a guessing game. Some things will work out beautifully, while others will be a disaster. But if you give up the first time something goes wrong, you won’t be self-employed for more than a month or two. You have to ride the waves and understand that it’s not a matter of whether something will happen – it’s a matter of when it will happen. And you have to be mentally prepared to fail on a very large (and sometimes very public) level, then dust yourself off and bounce back.

Lesson #4: Self-employment is amazing.

My two years of self-employment have been a continuous experience in dealing with things for which I was not prepared. I’ve dealt with some major medical issues. I’ve had several family members lose jobs and live on my couch for different periods of time. I’ve had emails that weren’t delivered, deadlines that were missed, and clients who wanted to strangle me (or vice versa). I’ve panicked while waiting for invoices to be paid because my checking account was down to $14 and my gas tank was empty.

Despite all that, the past two years have been the greatest of my adult life. I get to wake up every morning, throw on a bathrobe, and walk down the hall to my office. I get to spend time with my teenage son, who spent his early years thinking Mom was just someone who worked all the time and showed up every night an hour or two before bed. I no longer drive 100 miles a day to get to and from work. Most awesome is the fact that my income in 2013 (while still nothing to get excited about) is double what I made in 2012 and more than I’ve ever made in a year.

Through my business, I’ve had the opportunity to meet a ton of people who know A LOT about WordPress and the Genesis framework. I’m still blown away by the fact that I can talk to people like @bgardner and @photomatt on Twitter and they actually respond – because they’ve been where I am and they know that relationships mean everything. I’ve also helped build some great websites and watched my clients go from terrified to competent as they learn to use WordPress on their own, which is the reason I started this business in the first place.

What I’ve learned: If you have skills people are willing to pay you for, and you can stomach the uncertain paychecks and potential disasters and stresses of running a business, self-employment can be a fantastic way to earn a living. I have never once regretted the decision to abandon my former career and do what I love, and I wake up every morning thankful for the opportunity to keep doing it for at least another day. I just wish I had made the leap sooner!

What You Can Take Away from My Experience

Two years isn’t much in the grand scheme of things. I’m still a baby in the world of working for myself, and I still learn new things every single day (and I have a feeling that will continue no matter how long Nuts and Bolts Media is in business). I have no idea what will happen with my business next year or even next month! I know what I have planned, but I also know that those plans will likely change.

If you’ve ever considered quitting your job or starting a business, I’m here to tell you – it’s not for the faint of heart. That said, I can’t even describe how rewarding it is to have complete control over how I earn money, the hours I work (more like which 20 hours of the day I choose to work), and the services I offer my clients.

There is no magical formula that will help you start a successful business. There is no class you can take or ebook you can read that will transform you into the CEO of a multimillion dollar corporation overnight. But there is also nothing to stop you from doing what you love if you’ll put in the effort. The internet has created a global society where literally anyone can work for themselves. If it’s possible for me, it’s possible for you as well.

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  1. Despite all the trouble, it sure sounds like it’s been worth it! And doubling your income from a year ago is huge!

    It’s crazy how quick time flies. My two years will be officially June, 2014 when the paycheck a stopped coming in. I enjoy it immensely. Hard to ever go back unless something awesome just fits!

    Good luck! Any suggestions on why can do a banner redesign btw?


    • I agree – I can’t see myself ever going back to a “real job” unless some amazing thing happened to come along. It’s been a rollercoaster for sure but I wouldn’t trade it!

      I do graphics – let me know if you need a banner done and we can talk more about it.

  2. Great insights Andrea. I can sympathize with just about everything you mentioned. As much as running my own business can be tough, I wouldn’t trade it for anything.

  3. Great post Andrea — I really enjoyed reading this!

    It sounds like it’s been quite a whirlwind journey, but clearly doubling your income in 2013 shows amazing progress!

    I wonder at what point you consider expanding with another employee (part-time most likely) to help take some of the less value-added items off your plate and allow you to focus on the things you’re best at? I look at your twitter feed and it seems like you’re always working these insane 12+ hour days!

    I didn’t realize you were a psychotherapist! And you drove 100 miles each day??

    • I’ve hired contractors at various points in the past, but unfortunately it has never worked out well. I have yet to find people who will do things the way I want them done (and I’ve lost several clients when a contractor failed to uphold my standards for quality). The downside, as you’ve learned personally in the last month or so, is that when things get crazy, I run out of hours in the day and projects get pushed back. (I’m working on your stuff today, by the way.)

      Yep, I commuted 50 miles each way for 7 years working as a therapist, plus 5 years of college and grad school before that. One of the disadvantages of living in a rural area for sure! I could still make that drive with my eyes closed, and I’m grateful every day that I don’t have to spend 2 hours in the car to get to and from work.

    • I’m glad I’m not the only one who deals with chaos from time to time. That’s why I love networking with other designers so much – it always reminds me that I’m not alone in some of the craziness that seems to come up!

  4. I’m right behind you in years. I’ve only been into the WordPress web design business for a year. I would have guessed by your work that you had been in it longer than 2 years. I want to be like you when I grow up!

  5. Great post. I like your other comments can definitely relate. Even though I’ve been doing this for the past 9 years a lot of what you talked about continue to be true. Keep up the great work and keep doubling your income.

    • Thanks for stopping by, Greg! I’m not sure whether to be relieved or depressed to know I’ll still be dealing with some of this stuff for years to come. But I guess it always helps to know others are in the same boat.

  6. Joshua Sutterfield

    I think you really put things into perspective. Running a business is never as easy as one might think. There is a lot of figuring out that you have to do. I am always amazed at how I can come up with a great idea, only to realize that it was not so amazing begin with. Definitely a lot of trail and error.
    Like you, I come from a professional background. I practiced law for a number of years before starting a consulting practice. Your comment about doing work for friends really resonated with me. I never know what to charge them. If you discount your services too much, then they do not value your work. On the other hand, they seem to expect to pay a fraction of what your charge. I don’t think I’ll ever figure out this one.

    • Dealing with friends is definitely still a tough one for me as well. I try to cut them a break when I can – for example, I might charge a slightly lower rate for certain things – but when it comes down to it, I still have to earn enough to make it worth my time. Lately I’ve been telling friends, “I can discount this, but I’ll have to report it as a loss on my taxes, which means it will be considered income for you. Are you okay with that?” It’s amazing how quickly they’re ready to pay full price when they think of how it might affect them instead of just wanting a lower price.

  7. This is a great account of what to expect, and (I think) very accurate. Building residual sources of income is imperative for the lean times, and appreciated when they aren’t. Persistence is key and learning how to handle the volatile ups and downs of self-employment is what eventually brings fulfillment and success. If it were easy, more would do it. Thanks for sharing!

    • Thanks for your comments, Michael! Totally agree with this – “If it were easy, more would do it.” I think a lot of people try self-employment thinking it’s going to be easy, but they quickly become educated on just how much work it involves. It’s not for everyone, but I am definitely loving it overall!

  8. What a crazy ride :) I can’t believe it’s already been two years. I remember reading about your job and your first clients. You just reminded me that I have to write one of these in a couple months too.

    Sorry I couldn’t have been more help when you were being attacked but glad I was able to ease your mind a bit.

  9. Happy 2 year Quit-o-versary!!!!
    I feel your post is spot on. I’ve learned many of those lessons as well.
    Congrats on doubling your income and here’s to tripling your income in the new year :)

  10. Hello Andrea, congrats on your 2-years of online business sucess it’s surley a great things to have your own business and to be able to set your own hours and goals

    Thanks so much for sharing your tips with us also

    Most of us are building some sort of onling business and in hopes of one day to being an independent business owner. WordPress has given us so much as far as the tools to make it all happen.

    I wish you all th best in the days to come have a wonderful day. RobG

    • Thanks for visiting and sharing your thoughts, Rob! It’s amazing how many people I meet who are either working for themselves or hoping to one day. WordPress makes so many things possible – it just amazes me. Sure beats the days of writing HTML from scratch!

  11. Ginger

    Hello and thank you for sharing Andrea. I’m new to the WordPress, Genesis community but I’m hooked — in “sponge” mode soaking up as much as I can get. I am a real estate broker and also have a tech “day” job. I realize as I read your post it’s never going to be the “perfect” time to go out on my own….not sure how WordPress will integrate into my real estate back end systems but it will, of that I am sure. I go to sleep and waking up thinking about it (in a good way :-) . I will need to take that plunge soon to be able to call my own shots…at least then your hours working are your own instead of someone else’s product that my heart is not in.

    • Hi, Ginger, and thanks for visiting! There is definitely not a perfect time – I didn’t go into detail here, but my decision to leave my job was more necessity than choice. At the time, I was paid by the billable hour instead of receiving a salary, and Kentucky made the decision to privatize Medicaid, which severely limited the number of hours I could bill my clients for therapy. Suddenly my paychecks were about 1/5 of what they had been before. If I hadn’t been designing and doing freelance writing on the side, I wouldn’t have been able to pay my bills! After awhile, I started wondering why I was turning down design work to go to my job when I could make much more with design.

      Self-employment is tough, but it’s worth it. If it’s something you want to do, I hope you find a way to make it work! :)

  12. Congrats on two years. While it us very much part time still, I recently hit the two year mark with my SEAM Publishing, which is rashly an extension of a childhood dream.
    I think the most important lesson that I’ve learned is that you have to pick a business that people actually want to pay for!

  13. As always, I’m a HUGE fan of all your work and think you have succeeded immensely in 2 short years. As you become more established, I think you will enjoy charging premium rates for your premium work. I’m excited to see all your Wordpress training projects start! Happy holidays!!

  14. Ashley

    Wow, I can’t believe you went through such a tough time! Good for you for sticking through it :) Have you ever thought about becoming a Reseller for a hosting company? You can set your own pricing and make commission, then each client would have their own account, too. I only know this cuz I work at GoDaddy haha. It’s definitely what I am going to do when I get up and running properly. Thanks for sharing your experiences! Even though it’s not always a walk in the park, I want nothing more than to be like you!

    • Reselling doesn’t appeal to me at all because I have no control over the hardware – the whole reason I got into hosting is because the big hosts suck on such a spectacular level. (I’ll refrain from my usual GoDaddy rant since you work there.) The money wasn’t worth the time it took to provide support, though I definitely enjoyed the money at the time. I just have to find bigger and better ways to earn in 2014. :)

  15. Thanks for sharing Andrea! Sounds like you had an absolute nightmare with those DDoS attacks. The problem with these kind of attacks is as you said – there’s not much you can do about them while they’re happening, you just have to make sure you put those preventative measures in place to stop them from happening again!

    • Exactly! In this case, since the attack was ordered by a competing host who got angry with me, there was seriously nothing I could do until he decided to call it off. But that’s what happens when petty people use the internet. 😉

  16. helim

    Hye Andrea.
    1st of all..i would like to say thank you very much for sharing this kind article. i have read a number of books and website,your article somehow resonate me very well. I am currently thinking to quit but there was a day that i feel so certain to quit and there was a day also that i think i should just stay this 9-5 core instead. but after reading yours i thought that maybe i just give a try for 1 year…(due to the fact that my financial strentgh). wish me luck.

    • Woohoo congratulations and good luck! Having some time to try it out “safely” (with money in the bank just in case) is a wonderful feeling. I hope your experiment is a success!