I Quit My Last Day Job in 2015. Here’s What I Wish I’d Known Then.

Or: I love being self-employed, but . . .

One thing about me is that I really hate having a job.

Not working. It’s just the circumstance of having a job that requires me to work for someone else that I dislike. I always have. I don’t mind learning a new job, but as soon as I’m competent, I want to quit.

Having a job makes me itchy. I’ve had some pretty cool ones. I was a teacher. I was a social worker. But — same story every time. As soon as I’m past that honeymoon period where everything is new, I start to deeply resent everything about it.

An entrepreneurial spirit was bred into me, I think.

I was raised by a serial entrepreneur.

When I was ten years old, I started going to events with my dad where he sold collectibles. Everyone there sold collectibles in big glass cases.

And fourth-grade me showed up with a roll of paper towels and a bottle of Windex. I wandered around the events for hours, offering to clean the cases for a dollar. And at lunch time, offering to make a concession-stand run for dealers who were manning their booths alone.

That was exciting. I made my own money, to buy my own stuff.

I made $200 running a lemonade stand with my sister in the early 1980s. I’ve owned a vintage clothing store. I’ve owned a document preparation business. I’ve operated tutoring services, run a writing school (my current and favorite entrepreneurial enterprise.)

Being a single mom for most of the late 90s and early 2000s helped me to learn how to really appreciate (and love) income streams. Especially because I was a single mom with a kid who couldn’t go to daycare.

Now I see income streams everywhere. Kind of like that kid in who sees dead people, but way less scary.

I’ve had some pretty cool day jobs, but not one has compared to being self-employed. But I just really love being the boss of myself. With all that said, though, there are a few things I wish I’d known before I quit my last day job.

There’s almost no sleep involved with being the boss.

I don’t care what anyone says about four-hour workdays or how many ads popup on my Facebook Feed that show someone sipping margaritas on the beach while their passive income roles in — working for yourself is damned hard work.

And you’re the boss of it. That means it’s your job to make sure everything gets done.

These days, I own my own business. I work sixty to eighty hours a week. I earn about what I would if I were a school teacher — so I’m not getting rich over here.

(And that earning is in theory anyway. Because guess who doesn’t get paid if there’s some expense or shift in the matrix that affects my business’s bottomline.)

I don’t have anyone to pass the buck to, which means not only am I working a lot, I’m also stressed by any number of things on the regular.

Bottom Line

Being self-employed isn’t for the weak of heart. And quitting your day job definitely does not equate to working less (usually.) Most of the time, it means less sleep, because you’re both the overworked employee fighting for her job and the hard-ass boss who requires that kind of dedication.

You don’t need to buy all the things you might think you do.

The instant that the world learns that you’re opening a business, you’ll be bombarded with people who can help you.

No air quotes. Many of them really can help you. And that is actually the problem. When you’re overwhelmed, someone telling you that they’ve got the answer is so compelling.

The problem is that with all of it coming at once, it’s really hard to know whether this business coach, that sales platform, or maybe an online course about building your audience is essential right now.

It all feels pretty damned essential. And there’s the whole problem of not knowing what you don’t know.

The honest truth is that most of those things, you don’t need. And I can almost promise that at some point, you’ll regret buying most of it.

If I could do it again, I’d probably find a coach earlier. One person whose opinion I trusted and who specialized in keeping people with ADHD from burying themselves in too many ideas.

I’d bypass most of the courses I sign up for, because almost none of them went deep enough to really help me. A good number of them gave me just enough information to confuse me. And, you know, make me think I needed the next class or to hire the teacher to hold my hand.

(They did teach me a LOT about what kind of teacher I want to be, though.)

I bought more programs and apps and limited-time-deals than I can (or want to) add up right now. Only a tiny fractioned ended up being truly essential, or even really useful.

On the flip-side, I wouldn’t wait.

If I’d waited until I could afford to start a business before I invested any money into it — I’d still be waiting. It never would have happened.

Instead of worrying about the expense of starting my own business, I jumped in headfirst. And I’m glad that I did.

All of the gurus and boss babes shooting classes and memberships and free discovery calls and apps and tools and . . . yeah, everything at me only served to freak me out.

They made me feel like I was missing some key piece of information that could have if I spent $97 and hours of my time watching pre-recorded videos.

But there were a few things that I’m glad I did in the beginning, even though the cost was a little scary. A really good email server. A really great class about building my email list. A mastermind that gave me a really close-knit group of people who were also starting businesses. Hiring an assistant, just for a few hours a month at first.

Putting some money in made it real. And those things really helped me. But there were lots of things I thought I needed that I didn’t.

Bottom Line

Quitting your day job so you can start working for yourself can feel like a massive money pit, but it doesn’t have to be. Find someone you can trust and get their opinion about what you really need and what you can pass on.

Starting a business is a massive dopamine hit.

I was diagnosed with ADHD last year. At age 50.

ADHD is a dopamine-receptor issue. That translates to this: I’ve spent my entire life chasing a dopamine fix.

For me, that means that I shop too much. Especially in the winter. And I eat too much. And I seek out opportunities for idea generation and massive problem solving.

I could spend the rest of my life planning out new classes, finding income streams, organizing promotions, and figuring out how to grow my email list.

Those things shoot me full of dopamine.

That’s all well and good. But the problem is that I seek out that dopamine high all the time.

Sometimes it causes me to go all in on something that’s perhaps not the best idea I’ve ever had. Someday, I’ll tell you about the roughly two zillion good starts I’ve had that fizzled. Or exploded.

Sometimes it kicks me into full-on ADHD mode, digging in and desperately trying to make something work, when walking away would be better.

Because I’m constantly looking for that dopamine, it’s really hard for me to put up a barrier between work and not work. Good example: I’m going with my daughters to Pittsburgh for a quick two-day trip. And I’m finding it almost impossible to turn off my work brain.

Really, nearly entirely impossible. And it’s been that way for eight years. When I have a day job, when I’m not working, I don’t think about work at all. But as an entrepreneur? The line between work and not work is blurry.

And part of that is because when I’m working, my brain is dowsed in dopamine.

I wish that I’d known that I had ADHD when I started my business. I could have built in systems to help me deal with things like spontaneous new programs that come to me full-formed in the middle of the night.

But I know now and it’s still hard.

Bottom Line

This might be hard to believe, but stay with me here. Starting your own business can be pretty addictive. It feels so good to solve a problem or figure out how to do something hard or have even a tiny success.

That dopamine, though.

Then there’s the panic that tells you that if you slow down, at all, everything is going to collapse around your feet.

I highly recommending establishing boundaries between work and not-work right from the start. It might seem silly when you’re pre-revenue, but I promise you it’s not.

I wouldn’t have it any other way.

I love that I get to do exactly what I love the most while I’m working. Sometimes it hardly seems possible that I get to be paid for writing and talking about writing and thinking about writing.

That doesn’t mean that it’s all cookies and cream, though. There are a some things I might have done differently, with the benefit of hindsight.

Here are some of them.

1. I would have been more content with slower growth, instead of beating myself to a pulp trying to build as fast as humanly possible.
2. I would have saved my money on my first coach.
3. I would have been more confident about my prices.
4. I would have kept things small for longer.
5. By small, I mean simple.
6. I would have been more protective of days off right from the start.
7. I would have created a business plan.
8. I would have bought way fewer classes. I didn’t think I knew enough and I was always afraid I was going to mess up and do something to make my whole business go away. There was only one class that really made a difference for me and if I could go back (and have that hindsight,) I would have skipped all the rest.
9. I would have made myself sleep more.

I’m curious what you think about self-employment. Is quitting your day job something you’ve done or something you dream of doing?

Shaunta Grimes is a writer and teacher. She is an out-of-place Nevadan living in Northwestern PA with her husband, three superstar kids, Louie Baloo the dog, and Ollie Wilbur the cat. She’s on Instagram @ninjawritershop and is the author of Viral Nation, Rebel Nation, The Astonishing Maybe, and Center of Gravity. She is the original Ninja Writer.

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