10 Surprises of Self-Employment

Two years ago, I left my tech job for what are now well-known reasons endemic to Silicon Valley. Happy Freedom and Sanity Anniversary to me!

Two cups, more than half full.

These 10 things have surprised me most during my transition from a “good job” to a great life. I hope they help other folks who are considering self-employment, especially fellow table-flippers.

  1. The things people actually hire me to do are not the things I expected to do, but are some of my favorite things to do.
    Customer demand aligning with my interests is either uncanny happenstance or, perhaps, some magic by which I subconsciously attract the work I enjoy most. Whatever the reason, this is the most pleasant surprise of all. I thought people would need statistical data analysis but not instructional design, and financial strategy more than in-depth user research. I never even conceived of ghostwriting for executives who do not have the time and space to write on their own. I was wrong, happily so.
  2. My shift to self-employment brought my tax accountant out of his shell.
    My tax accountant, Dan, is a terrific, astute, and helpful guy. He is also quiet, deliberate, and reserved. But when Dan and I had a call to discuss my questions about self-employment, he bowled me over with brilliance, encouragement, and savvy advice from running his own successful business. Anticipating a quick chat, I called Dan from my car, parked outside of a restaurant where my husband and friends were gathered. An hour-and-some later, I joined them. My notebook was full of advice and to-dos, and I was full of confidence about my choice. I never figured my tax accountant for one of my best supporters.
  3. Switching cost is high, I have yet to master it, and variety is still the spice of life.
    As an engineering manager, I visibly cringed when executives failed to account for switching cost: “Oh, that developer is ‘only’ four days a week on Project A? He can spend Wednesdays on my stuff, Project B. I need more bodies!” They did not realize (or care) that Project A and Project B did not share a code base, or that the developer would need time, every Wednesday morning, to remember what he’d been doing and review what had changed in the past week. And forget maintenance and bug fixing time: generating new code is the only thing that counts! Well, I know switching cost, but I still don’t have a fix for it. I love working on two totally unrelated things for two totally different clients, but shifting from Project A to Project B takes time, and that time is not billable. It could be, but I do not feel that billing for switching cost would be ethical. It’s just one of my costs of doing business.
  4. Freshbooks is one of the best pieces of software in existence, in all the universe.
    Freshbooks is my self-employment life saver. It does it all, and not a thing more than it should. It makes pretty invoices, imports business expenses from your bank account, connects to online payment, and has a log-in for your accountant come tax time. It is affordable and… wait for it… equally pleasant to use on web and mobile. Whatever code-a-ma-bob you’re designing, spend time on Freshbooks and learn a little something. In the Long Long Ago, in The Time Before, we believed in user-centered design principles. I figured them dead, killed by massive pop-ups, auto-play video, forced account creation that prevents people from giving you their money, and daily emails requesting product reviews, just to ensure I never purchase them again. Freshbooks assures me this is not so.
  5. First Republic is the only sensible place to open a business banking account.
    The branches have free chocolate chip cookies! They have special days where they shred your documents! Bypass every other bank and head for the forest green and the golden eagle, my pretties. Other banks claim to have business bank accounts, but they lie. These banks laud the fact that they do not have branches and few ATMs. “You can do everything through your phone,” they say. Then you try. And the mobile deposit doesn’t work in the app, or at least not with the version of the OS you have. Even if it did, the “business” account has a mobile deposit limit of $1,500, because it wants you to be poor. So you drive to a far-off suburb to use one of the precious few ATMs, and find that it has a deposit limit of $5,000, as well as a withdrawal limit. Skip it. 
    (No, I am not a paid spokesperson for either Freshbooks or First Republic. Sad.)
  6. Corporate behaviors are human behaviors.
    I do not know why, exactly, but I did not expect to find certain behaviors outside of full-time office environments, specifically: attention deficit disorder (ADD) and/or impatience when it comes to product implementation (humans love ideation but the harder work of execution less so); killing a product before it has a week or even a month to succeed; reacting to market forces too soon (this is why we don’t check our 401(k)s every day); and the expectation of competitor outcomes at a teeny fraction of the competitor’s investment. Self-employment can’t save you from every aspect of corporate life.
  7. My not-so-big house is a tax bonus.
    I adore my small, cozy home and its super low utility bills for myriad reasons, but self-employment revealed another one: The smaller your house, the larger your home office deduction as a percentage of space.
  8. I still haven’t made business cards and a professional website.
    It’s not that I don’t want to, so much as it is the cobbler’s children having no shoes. I need to Do The Thing, I really haven’t had the time, and I expected to have the time.
  9. I do not miss going to an office. At all.
    I am an introvert. I have a very low tolerance (none) for noise, a super sensitive sense of smell, and I actually like to do my work, diligently and without distraction. For these reasons, open-plan offices are my nemesis. They are often full of noisy, smelly, distracting, not-working people. (Bathe daily, with soap. Please. And no, a vegan diet has not altered your need for deodorant. Sorry.) I never liked commuting, either, not that anyone does. Now, when I accidentally find myself out and about at commute time, the scene appears barbaric. People weep openly, shout into their phones, drag their half-asleep kids along the sidewalk... It makes me want to cry. I get plenty of social interaction from my clients, friends, in classes I take, at the local gym, in my friendly neighborhood, through volunteering with my neighborhood association, and my writers’ group.
  10. I have lived two whole years without sexual harassment (mostly) and pay discrimination. It’s a whole new world.
    I wish this experience for all humans, everywhere. I now know what it really is to live two full years without a single text message from a VC asking me out on a date; without a manager asking me if I plan to have children or take maternity leave; without the unpaid emotional labor of fixing people problems that gutless “leaders” and HR refuse to take on; without massive pay disparities. Bliss is too light a word. I did not, could not, realize how much time, stress, and mental overhead I had to allocate to these energy-sapping things until they were gone. Now that I can invest all of that energy in my business, my household, and my life, I realize how much others were taking.

Stephany Wilkes is a writer, consultant, and sheep shearer. She is a regular contributor at Hobby Farms. Her work has been published in The Ag Mag, The New Stack, Midwestern Gothic, various academic publications, and on her blog, West by Midwest. She has recently completed a book about her sheep shearing adventures called Raw Material, and is at work on another about fiber plants and fabric being grown and woven across the U.S.