How to Be Self Employed for Dummies

Wondering what it takes to be self-employed? Have you seen friends online sharing their rags to riches stories, and met people at company fundraisers who are business owners, working for themselves, and living it up?

Maybe you’re thinking:

  • I don’t have enough time to work a full-time job AND build a business
  • I have kids and a family and can’t focus on a business right now or risk our future
  • I didn’t study business in college, and can’t afford to go to grad school for an MBA

The great news is that being self-employed and (creating additional streams of income, making money off your hobby, or starting a business from the ground up) isn’t just for the rich people who have it all together.

I’ve been self-employed (in one way or another… I have gone back to jobs I quit) since 2016. I can tell you from personal experience and from having a bigger online network than any amount of friends I’ve ever had in my entire life that it rarely happens on purpose, according to some meticulous plan you create for yourself (or purchase) and follow step-by-step.

Here are some tips for how to be self employed and take your first steps on your entrepreneurial journey

Don’t do it for the money.

Unfortunately, the biggest eye sparkler about having a business is the money. People who own their own business tend to be rich, right? They can lease nice cars, write off airfare upgrades, and all that jazz? 

Maybe. Eventually.

But when you’re first starting out, any successful (or even unsuccessful!) business owner will tell you: Don’t do it for the money. For several reasons:

  • Being self employed  doesn’t pay a lot in the beginning. If you take a leap of faith, quit your job, and rely on your savings as you build this business that HAS TO WORK, you’ll be surprised to find yourself working 100 hours a week to get about a quarter of the money you were expecting. At first. But if you follow a strategy, work with someone who’s experienced and knows their stuff, then you can make fast progress. But the money won’t come the way you planned, most likely.
  • You have to be motivated by something other than your bank account and personal security, especially if the bottom line, foundational reason for your product or service is to make a positive change in the world. Money will come in abundance, run out, reveal good and bad characteristics about people (including you!). In our modern American education and culture, we’re not very experienced with money and finances. Unless you grew up in a nurtured, entrepreneurial environment where your parents helped you put the money you earned away and detach your worth from it (I mean, that’s pretty much nobody, right?) then you’re going to be learning about money AND a bunch of other stuff as you become self-employed, like leadership, self care, mental health, physical health and sleeping patterns, etc.

Make sure you’re as infatuated with the self-employed, entrepreneurial culture as you think you are

On the outside it’s easy to think that entrepreneurs have lots of time, are always laughing while holding cute coffee mugs, and only post some (but not all) of their photos next to private jets and sports cars.

In reality, entrepreneurship is:

  • Figuring out how modern marketing actually works (not the old school flyers and door-to-door sales your parents and grand parents swear by)
  • Spending money before you make any money (there are lots of tools that cost $30+ per month that eventually you’ll realize you can’t avoid purchasing.)
  • Putting an end to the smack talk and judgemental thoughts you have about others, because ultimately you’ll start assuming other people think that way about you (and they don’t. Entrepreneurs are some of the most supportive, positive people, if you can get over your own skepticism that there are any more good people in the world)
  • Re-framing how you feel about rich people. We’re all jealous of rich people at some point. You’re going to meet some really kind, soft-hearted, welcoming rich people who will challenge everything you’ve ever thought about rich people, ever. You may even come to realize that many of the so-called “trophy wives” you’ve been hating on all these years (*raises hand*)  are actually self-made millionaires or six-figure earners, buying a ridiculously high priced fake plant at Target because they’re in launch mode and trying to get their mind off all the things that could go wrong. 
  • Meeting a whole new network of people you’ve never touched before. This is as terrifying as it sounds, at times, and will often bring you back to the first day of 4th grade at a brand new school where you genuinely just want friends but you’ve got a mean voice in your head saying everyone hates you. Go make friends with entrepreneurs of all kinds. Do you want more people like them in your life?

Warm your loved ones up to the fact that you would like to be self-employed

It’s true, you don’t have any time. You have 11 children and 5 jobs and your house is on the verge of burning down at every moment. But you do have little pockets of time here and there, and now that you think about it, you have a pretty nice family that would support you if it came down to it.

You’ve probably never actually asked your kids or partner, “Is it okay if I leave for about 4 hours this Saturday to go write something that’s really important to me? Can you manage without me?” 

If they completely fall apart at the mere thought of you not being around, well, you’ve got other things going on, then. But let’s say they’re like “Um, no, mom, we totally can’t do that. How about 2 hours? 1 hour?”

Done! That’s 1-2 hours of solo work time than you had before you spilled the beans on your dream project. Yay, you!

Be open to the conversation that this sparks. Channel your inner Brene Brown. Be vulnerable, and plant the seeds in your family.

Start small. Ask for advice. Talk about your intentions… A LOT.

Whenever you have the chance to tell someone about your idea for a business, TELL THEM. Successful businesses aren’t built by following the top-ranking digital course on “How to Be Self-Employed and Start A Business.” They’re created through community and storytelling and the deep desire we all have to help. 

Tell your grandma about your idea. Tell your co-workers about what you’re doing (provided there’s no conflict of interest, or you work with assholes). Tell the guy you keep seeing at the coffee shop who seems to enjoy candid conversations with strangers. Tell your gamer friends while you’re waiting for the level to load that you’re exploring different ways to be self-employed so you can work from home like you’ve always wanted to. 

Work with a business coach you trust

Business coaches come in all shapes, sizes, modalities, languages, and prices. Spend some time networking and asking for recommendations instead of relying on Google to tell you who to trust. I realize that’s ironic for me to say, as a business coach that you may have found via Google, but I stand by it. Don’t work with a coach and rely on a stranger to learn how to be self-employed based solely on their website or carefully manufactured email newsletters. I’m not saying people are lying or being dishonest, but it is possible for someone to hire a website or marketing copywriter and SEO expert to make them appear to be a better fit for you than they may actually be. 

Get to know them. Follow their feeds, attend their livestreams, and DM them on Instagram to see how they treat strangers. After all…


And, shameless plug: I’m a business coach. I can totally help you. Feel free to friendly-stalk my Facebook Page and Instagram profiles and DM me anytime!

Based on what you’ve learned in this post, how do you feel about being self-employed now? 

If you have a burning question and want a real answer, simply ask it in the comments!

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