If you want to fail at self-employment, I know every trick in the book. Lemme ‘splain.

How to #Fail

So you’ve decided to self-sabotage your self-employment experiment. You don’t want to languish in mediocrity. No. You want to go down in a ball of flaming glory, botching every job, missing every gravy train, spending all of your savings, and crawling back to your Old Boss a month later. If so, you’ve come to the right place.

  • Have an empty savings account. When you start your self-employment adventure, make sure your savings account is empty. If you have three months’ worth of liquid cash in the bank, there’s a good chance you’ll accidentally succeed. With six months’ worth of cash, it will be very hard to fail. Beware.
  • When you don’t get a call-back, panic. It’s going to take time to build up your client list. A great way to make sure you don’t survive the first two years is to freak the funkles out any time you’re not working. Think about missing your rent payment, losing your apartment, and having to move your family into your Mom’s basement. Think about the humiliation you’ll feel, and the utter helplessness that comes with financial insolvency. Tell yourself that it will not work out in the end. Imagine your would-be clients laughing at your proposal, using it as toilet paper, and making blood pacts with their hiring buddies never to hire you. They are not busy, distracted, or disorganized: they are simply doing it to spite you.
  • Be a perfectionist. It’s crucial that your website be pixel perfect before you contact your first client. Accept nothing less than absolute perfection.
  • Spend money to make money. You’ll need at least 5000 professionally-designed business cards, a custom domain name, a call center to answer your phones, and a social media manager. Buy a $17k iMac Pro, an Objet260 Connex3, and every cool-looking peripheral you can find. When you build a website, build it with big-data in mind. AI is big: invest in it. Sign up for Salesforce.com, Hootsuite, and buy CATIA. Definitely CATIA.
  • Focus on one job at a time. Once you land a client, rely on them implicitly. Never do more than one thing at a time. Never look for new clients during a job.
  • Stick to one revenue source. If you want to fail at self-employment, make absolutely certain to rely on one and only one revenue source. Do not look for independent revenue streams, and never look outside of your normal area of expertise. You should feel very uncomfortable about trying new things, and, if you absolutely can’t stop yourself, be sure to comply with the perfectionism principle outlined above.
  • Do everything yourself. If you need accounting software, you can save money by making an insanely complex spreadsheet rather than using any of the cheap, readily-available off-the-shelf solutions. If you need a website, be sure to code it from scratch by yourself, and remember that it needs to reinvent the whole idea of “website”. (No website in the history of websites has ever been like yours.) If you need a logo, save money by having your brother-in-law’s twelve year old son. He has Photoshop, and loves art. (Note: Be careful not to conflate this with the spend money to make money principle: you want to spend exorbitant amounts of money on things that are not important, but be sure to pinch every possible penny on the things that actually matter.)
  • Do not work with others. Partnerships are far more likely to succeed than sole-proprietorships. Avoid them. Be sure not to ask other self-employed people for tips: they will be offended, irritated, and dislike you for asking. Working well with teams is a huge liability when trying to fail.
  • Only think about taxes in April. This might just be the number one tip for failing as a self-employed person: do NOT, under any circumstances, think about tax liabilities until it is absolutely necessary to do so. In the US you can expect that liability to be around 30-35% of every check you receive, but don’t set it aside. Spend it. And don’t think about any of the other ways you are being taxed, and how those affect your bottom line: you should consider each dollar of revenue as a dollar of profit, and spend every penny.

There are far more ways to fail at self-employment than I could possibly list in a single article. Maybe in a future piece we can talk about some of the more nuanced ways to sabotage your work, increase your stress levels, and ruin your life and marriage in the process.

Until then, keep the faith! If you can stick to even one or two of the principles above, you are well on your way to epic failure. Good luck.


Adam O'Hern is an industrial designer, designing products ranging from laptops to power tools, classroom toys to bathroom fixtures, and pro audio gear to guitar tuners. In 2008 he founded cadjunkie.com, and in 2010 co-founded EvD Media with Josh Mings of SolidSmack.com, and the two collaborate on the EngineerVsDesigner.com podcast.