I read somewhere recently that entrepreneurs are more likely to have ADHD than any other profession. I think I was supposed to be surprised by this, but my first reaction was actually more along the lines of, “Well, yeah.”

The things that are so difficult for people with ADHD are the things that are put in place in our school systems, and our employment systems, to keep everything in order and running smoothly. But ask anyone with ADHD about how well they fit into a system like that, and I don’t think the words “order” and “running smoothly” will occur to them.

And after twelve-plus years of trying to fit into a school system that rejects your very nature, why would you then choose to enter into a workforce that does the same thing?

When you have a brain that excels at finding alternative solutions to a problem, it wouldn’t make much sense to follow the same paths—career or otherwise—as everyone else.

ADHDers thrive when their super-powered brain is free to do what it does best, and that doesn’t usually involve sitting in an office chair for 8 hours a day and taking arbitrary orders from an arbitrary authority figure.

I always knew I didn’t want a “boring office job.” Now I know I don’t really want any job.

A year ago, almost to the day, I quit full-time teaching. It wasn’t necessarily supposed to be a permanent career change; I figured I’d teach some private lessons for awhile, get a part-time job at a cram school, take a little breather, and then move on to another international school.

That was the plan, after all: to be a teacher. And I do love teaching. But after two years in what could only be described as the easiest teaching job on the planet, I was still totally burnt out.

Full-time work, it transpired, just wasn’t my thing.

I had a little money saved up, so I decided to try pursuing some creative work on my own and see where it would take me. I already had a dusty old Etsy shop that I hadn’t updated in years, and I’d heard about an online marketplace for freelancers called Fiverr. Best of all, I had a new iPad that I could use to draw, write, animate, and do pretty much anything I asked of it.

So I became my own boss.

This decision came just a few short months after my ADHD diagnosis, and I was definitely worried that my brain was going to collapse in on itself. For the first time in my life, I wouldn’t be following a set of schedules and rules and expectations that were laid out for me—I’d be responsible for creating and adhering to those things myself.

It was thrilling, but also a little terrifying. And there are definitely some specific challenges that come along with self-employment/entrepreneurialism/small business ownership/whatever you want to call it when you’re a person with ADHD. 

But there’s so much freedom that comes with it, too. As I’m learning about what my brain is really good at, I get to work those things into my schedule. I get to create systems that work for me, instead of trying to work around someone else’s one-size-fits-all-except-apparently-not-Rosie system. If I want to sit on the floor and eat blueberries while I do my work, it’s totally fine.

And yeah, I’ve failed a lot in the past year. And I expect to keep failing. But for every challenge that my ADHD brain gives me, it also has a superpower that helps me find a way around itself in some strange, unexpected, creative way I can’t really explain to most people. But hey, I’m gonna give it a try.

Here are some of the challenges and superpowers I’ve discovered so far, presented to you in the disorganized order in which they occurred to me:

Starting & Finishing Projects

The challenge:

My ADHD brain is a freakin’ supercharged machine when it comes to starting a new project (at least, one that I’m excited about). But finishing something? Not so much.

This was a source of a lot of shame and guilt at first, I’ll be honest. I’d get super excited about a project, dive into it headfirst, and then quit as soon as it started to get too hard or too boring or too real. And then I’d be left feeling like garbage for doing all that work and having nothing to show for it.

The superpower:

Here’s the thing: most of that guilt was coming from Past Rosie—the one who was always trying to answer to her teachers or parents or bosses’ expectations. Now I didn’t have to meet anyone’s expectations but my own, and suddenly the pressure was off.

And guess what? If that project isn’t fulfilling to me, I don’t actually have to finish it. If I start something that doesn’t end up being what I thought it would, I have no obligation to see it through. There’s no shame in deciding that something isn’t worth my energy, and I have no problem diving into something new and exciting.

Staying Focused

The challenge:

Okay, yeah, so staying focused isn’t my best talent. That’s sort of where ADHD gets its name, after all (even though it’s so much more than that). I can’t tell you how many days I’ve started with a goal in mind and then completely forgotten about that goal by lunch time.

I fall headfirst down internet rabbit holes. I start things and forget to finish them. I have five different Instagram accounts for the five different careers I’ve committed my life to (so far). An interesting bug on the balcony is enough to derail my workflow for the rest of the day. That’s just part of the deal.

The superpower:

After a life filled with people reminding you to get back on track, it’s daunting to suddenly realize that no one’s going to tell you to stay focused. But guess what? Staying focused isn’t the point.

As far as I’m concerned, the point is to do fulfilling work and make enough money to keep paying rent. And for someone with as many passions as me, staying focused on one thing would actually do more harm than good.

Thanks to my lack of focus, I have a steady stream of income coming from multiple directions—so if one of them falls through, it’s not the end of the world.  

And with so many moving parts happening at all times, it’s a rare moment that I’m not working on anything. Sure, it might take me twice as long to finish a project than it would for someone else—but that’s only because I’ve finished three other projects while I was taking a break from that one.


The challenge:

Unlike most neurotypical people (or so I’m told), my ADHD brain is not motivated by “normal” things like money or praise or rewards. My brain simply does not care how important something is… if it’s not giving me dopamine, it’s super difficult to make myself want to do it.

This is the reason that I’ve often found myself turning down work opportunities, even when I needed the money. Which, as you can imagine, isn’t always in my best interest.

The superpower:

After struggling to complete some freelance work that I really didn’t want to do—even though I was being amply paid for it—I had a bit of an epiphany:

 When I’m the boss, I don’t have to do work I don’t like. 

I don’t have to accept work that doesn’t align with my own interests—I just have to find the work that does. Once I realized this, I stopped marketing my freelance skills to anyone and everyone, and started focusing on potential clients that would give me projects I was actually excited about.

For example: One of my freelance gigs on Fiverr is to write lesson plans for teachers—it’s easy for me, and a surprising amount of people will pay for this service. But after a few projects for math and reading lessons, I was ready to pull my hair out with boredom. I didn’t want to stop offering that gig, because it was doing really well. So instead I tweaked it. 

Now I only accept offers to write lesson plans about creativity or social-emotional skills—in other words, the topics I’m passionate about. True, I don’t get quite as many requests anymore… but the ones I get now are almost always aligned with the type of work I want to be doing.

Work-Life Balance

The challenge:

Working from home means it’s super difficult for my brain to switch gears when it’s time to start working—and when it’s time to stop. My ideal 8am-4pm work schedule is usually shifted by an hour or two: I can’t get always myself to start working until 9:30, and it’s difficult for me to stop and eat dinner once I’m in the groove.

This might change if I had a studio or a workspace outside of home, but this isn’t really possible in the current pandemic. So I’m stuck struggling, at least for now.

The superpower: 

Still, this blurry line between work and life isn’t always a bad thing. Since I’m the one choosing the work, the things I’m working on are almost always in line with my personal interests. When I’m working on things I really love, it doesn’t often feel like work is “spilling over” into my personal life—instead, it feels like they’re supporting each other.

Time Management

The challenge:

My ADHD brain has a really hard time predicting how long certain tasks will take to complete. This means that managing my time can be next-to-impossible; I might give myself way too many projects with not enough time to complete them, or I might get stuck in the “I still have plenty of time” cycle and find myself scrambling when it turns out that no, I do not actually have plenty of time.

The superpower:

Time management is just one of those things that I expect to struggle with forever. With that said, not being tied to a specific work schedule means that I do have the opportunity to play around until I find one that works for me.

This is something I’m still working on, but I’ve found two tricks so far that seem to be working well:

  • Scheduling my time by day, rather than by hour. Thanks to my hyperfocusing skills (read: Ferrari brain), I can spend hours and hours working on something I enjoy. By devoting an entire day to a single project, rather than working on multiple projects a little bit every day, I’m giving my brain permission to go into full Ferrari mode and knock it out of the park.

  • When predicting how long something will take, I multiply my original guess by three. (For example, if I think it’ll take me two hours to write a blog post, I set aside six hours instead.) If I can get past the deeply ingrained shaming voice in the back of my head that says “it shouldn’t take you that long,” then I have ample time to get it done—and maybe even get a little hit of dopamine for finishing “early.”


The challenge:

Organization. Organization is the challenge. All of it.

The superpower:

I don’t have one. It’s just hard, okay? There are sticky notes all over the place. I can’t remember where I put that one thing I haven’t used in four months but for some reason I need it RIGHT NOW. I bought a bunch of highlighters one day thinking that would help me get organized, but now I just have too many highlighters. Please help.

Screen Time

The challenge:

This one’s a big problem, primarily because a lot of my freelance work is done on my iPad. I won’t lie, it can be really tough to manage my screen time—just like it’s tough for me to manage any kind of time—and there are definitely days when my eyes hurt and my brain is fried. (On those days, poor Oscar comes home from work to find that his loving girlfriend is no longer capable of human interaction, or of anything else, really.)

The superpower:

The sort-of-good news is that I get bored of looking at a screen too long, anyway—I have to be doing something with my hands while I’m working, or I’ll go crazy.

Plus, something about seeing something on paper makes things easier for my brain to absorb, which is a great excuse for me to get a break from screen time. All of my outlines, plans, and ideas go down on paper first, whether that’s in my planner or in the sea of Post-It’s on my desk. 

And there are other tricks, too—blue light blocking glasses, keeping “night mode” on throughout the day, and using screen time limits on my phone (which I promptly ignore whenever they pop up… oops).


The challenge:

Some days are just duds when it comes to productivity. I can set myself up for success the day before—to-do lists, timers, scheduled breaks—and still totally drop every single ball. Executive dysfunction is a bitch and a half, and part of having ADHD is just learning to live with that struggle.

The superpower:

This one took me awhile, but when I finally figured it out it was a game-changer:

Since I’m the boss, I’m the one who gets to decide what “productivity” looks like in the first place.

And when it comes to creative work in particular, productivity isn’t always tangible. Sometimes my most “productive” days are the ones that I spend daydreaming, or doodling, or talking to an old friend—because I’m planting the seeds for future success.

Honestly, if I spent as much time creating as I think I should be, a lot of those creations would probably turn out like garbage.

It’s been a doozy of a year, and I’m honestly surprised at how well things have gone so far. I had no idea what I was doing a year ago, and I have very little idea what I’m doing now—but somehow it all seems to be working out okay. 

And with that, it’s time to get back to work… The boss is looking over my shoulder.

‘Til next time,