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What I’ve Learned in a Year of Being My Own Boss

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I officially celebrated my one year quitiversary from my full-time job as a graphic designer last week. If you weren’t around back when the change happened, the story was a pretty common one. I worked in a decent job, with decent pay (and awesome benefits) doing decent work, and even though on paper everything was hunky-dory, I absolutely wasn’t fulfilled.

me champagne

Cheap champagne on the last day of work. Obviously, pre-pregnancy.

I know lots of folks just find a new job when they’re unhappy with their current one, but after seven combined years in two different office environments, I started to suspect the problem wasn’t the particular job or company, but an issue with me. I suspected that I’d thrive as my own boss, with my own hours and complete control over my workload—and I was right! Now, I work as a freelance graphic designer and food writer. Being my own boss has been the most amazing blessing. Sure, there are tough days still, but overall, I’m a much happier and more content person (and my husband will tell you—I’m much nicer to be around now). It feels amazing to be the master of my own destiny.

Me and my first cover article (and photo!).

Me and my first cover article (and photo!).

Now that I have a bit (a tiny bit) of perspective on the move to be my own boss, I thought it’d be fun to share some of the things I’ve learned over the past 365 days. If I’m fortunate enough to get to keep being my own boss, I’m sure I’ll just keep learning more and more! Okay, onto what I’ve learned:

There will never be a perfect time to quit.

Craig and I worked for years (literally, years) to get to the position where we felt like I could quit my job. My income was about 70% of our total income, plus I carried all the benefits, so it was a big shift to just drop that. We decided somewhere around my 27th birthday that I would absolutely not be in this job by my 30th birthday (having a date circled on the calendar really helped mentally and emotionally get through the rough days), and we worked almost every day of that three years to achieve that goal. We scrimped. We saved. We took on odd jobs and freelance work. We paid off debt. We lived in a tiny apartment. We shopped at Aldi. We never went out to eat. We didn’t travel much. We sold stuff to pay off credit cards. I had a side business selling purses and headbands on Etsy. And even with all that, we still weren’t in an ideal financial situation when I quit.

wristlet etsy

We were better off than a lot of folks, but financial advisors everywhere probably would have advised that I not quit. In an ideal situation, we would have had six months of living expenses saved up and all of our debt paid off. In reality, we had about two months of living expenses saved up, plus about three-quarters of our debt paid off.

Honestly, if we would have waited until the perfect time, I think I would have been waiting forever. I’m no financial expert, but just like everything in my life, I believe in the middle path. I wasn’t going to be naive enough to quit my job with $10 in savings and buried in debt, but also, waiting another 2-3 years to be even more financially secure was not worth the emotional and physical toll that job was taking on me. I’m not sure there is such a thing as a “perfect” financial situation. You can always have more in savings. You can always pay off more debt. You can always have more assets. I personally feel like if you’re waiting for “perfect,” you’re going to be waiting forever.

That first step is a doozy.

Yup, no matter how much you loathe your job, despise your boss, and dream of the day you can turn in your resignation letter, when the day comes—it’s a doozy. The fact is, you are (willingly!) surrendering all guarantee of future income. And regardless of how much you’ve saved and prepared, that’s terrifying. And just because your feelings are leaning a bit more toward total terror instead of total glee, it doesn’t mean it’s the wrong decision. It just means you’re realistic.

me feet stairs firetower

This is also the case for any times you might be wavering post-quit, too. It’s only natural to want to go back to comfortable (and comfortable=a steady paycheck) when things get shaky. Like earlier in the year, when we got our property tax bill and it was four times what we estimated and cleared out half of our savings. I had some serious thoughts about going out and finding another job. I’m glad I didn’t (because we obviously got through it, and I’d probably be stuck in a job I hated), but having a steady job you dislike is like being wrapped in a warm, cozy, abusive security blanket. And it’s only natural to have the urge to go back to that place sometimes—even if it is toxic. Although I could easily bring myself out of that urge by remembering how I’d cry more days than not at my job. That worked.

You gotta figure out if the positives outweigh the negatives.

Being your own boss and working from home sounds like a promised-land of pajama pants and flexible hours, but just like everything in life, there are negatives that go along with being your own boss, too. And the fact is, it just isn’t for everyone.

desk computer

I no longer get to put on a pretty dress and go to work. Which sounds like a positive, but when you’ve gone three days in the same jammie pants, you start to rethink that. I don’t have any co-workers. Again, it can be a positive if you think about that annoying loud-talking coworker in the next cubicle, but it also means you don’t have a work-BFF or anyone to rant with when something goes wrong. You are the CEO, the boss, the employee, the receptionist, and the intern. Being your own boss part? Awesome. Being your own intern part? Not so awesome. I desperately miss having a cluster of young, enthusiastic college students to do mind-numbing work like data entry and photo resizing.

You never get to clock-out. Some folks struggle with this at a job, too, but I was an expert at keeping my work life separate from my home life. When I walked out of those doors at quitting time, I didn’t check my email or take calls or do anything work related until I walked back in the next morning. That clear delineation doesn’t exist for me anymore. The benefit of that lack of delineation is that I have a completely flexible schedule. If I want to take all of Tuesday off to binge on Gilmore Girls, I can. But it also means I might be replying to emails at 3am on a Sunday.

For me, all these negatives (and more, there are more) weren’t enough to outweigh the stomach-turning dread that flooded over me every Sunday evening when I was working. But for some folks, a good ole 9-to-5 is the way to go.

It’s amazing what happens when you open yourself up.

You can either take this in a spiritual way or a literal way, but I was amazed at the opportunities that just kinda fell on my lap when I opened myself up. When I was no longer booked for 40+ hours a week at work. When I was no longer consumed with job dissatisfaction. When I was no longer closed off to the world.

Within four hours of announcing to the world that I was a quitter, I had booked three new clients. Sure, they probably saw that I was available (and maybe even pitied my lack of consistent income), but they were still opportunities that I would have never known existed if I had stayed at my job. Within a month, I had a book deal and a very fruitful partnership doing book design for a major publisher. I’m not a very spiritual person, but even I think the timing of it all is just a little too perfect to be coincidence. And I’ve heard of similar situations from multiple people who have taken the leap.

sliders spread cookbook

When you open yourself up to opportunities, the opportunities open themselves up to you. And the fact is, when you don’t have that backup net of a paycheck coming on Friday, you work harder and you are more willing and welcoming of any chance to prove yourself. There is something about taking that leap that makes you confident. And that confidence is what makes people want to pay you.

A lifestyle change is in order.

One of the biggest mistakes I made when I quit was that we didn’t change our standard of living. We kept living like we had a big ole paycheck coming in next month—and guess what? It didn’t come. It ended up working out for us, because I was able to book some big jobs early on, but that doesn’t always happen. And won’t always happen.


If I could go back, I would seriously cut back in those first few months. Eventually we realized that, hey, our income is no longer consistent and what we might bring in this month is in no way indicative of what we’ll bring in next month. And because of that, we have to adjust our baseline budget. Now I know how much money we have to bring in each month to cover our basic living expenses without tapping into savings, and that’s my financial goal for each month. If I make a little more, awesome, it can go to savings (to help cover months when I don’t hit the baseline goal), pay off debt, or buy us some gadget or doodad we’ve been coveting. If my business had a higher overhead cost, that extra money might get pumped right back into my business (but thankfully the overhead cost of graphic design and writing is low, low, low).

Where we live made this possible.

Even though I live in rural Indiana, I work in Manhattan, LA, Chicago, etc. thanks to the joys of the internet. Which means I can fetch those kinds of big city rates for my work. And when you combine that with the low cost of living of my little town in the Midwest, it works out well for us.

me babyface house

Oh, summer, how I miss thee.

Honestly, if we lived in a higher cost of living location, I’m not sure we could make it work. Our mortgage is low. Our property taxes are low (well, usually). Gas is cheap. Services are cheap. Milk is cheap. I was talking with some ladies at the Healthy Living Summit this year about cost of living in different locations, and our yearly income would barely cover the cost of owning a house in some areas of the country. We’re fully aware that where we live makes this transition much easier.

Being in control is incredible.

I always figured I’d probably like having complete control over my career, but it’s been so much better than I ever imagined. Having the freedom to pick my clients, pick my projects, pick my workload, and my pick my hours is such an incredible luxury.

Now I have the freedom to give a friend a discount or do pro bono work. I can barter my work.  I can turn down a project I really have no interest in working on. I can schedule myself a maternity leave (for as long as I want/can afford). I can experiment with new products and services without having to go through 27 layers of managerial red tape. I set my prices based on what I think is fair and reasonable. I have control. And it’s friggin’ priceless. If I ever do go back to the grind, I’ll have to do some serious work to get used to not being in control anymore.

The cobbler’s kids have no shoes.

Want to hear something funny? I’ve been working on my own as a professional graphic designer and writer for a full year now, and, I uh, don’t have a website. Or a portfolio. Or an up-to-date resume. And the designs on both Wholefully and the Broken Plow are in serious need of an update. I haven’t had any time to devote to my own personal projects.


Back when I was working at a job, working on my own personal projects on the weekend was a fun way to release some of the creative frustration that had built up during the week. But now? There just isn’t the time. I did manage to spend about four hours working on a website back in the spring, but I haven’t touched it since. Maybe someday I’ll actually have a website. Amazingly enough, clients don’t seem to mind that their web designer doesn’t have a website herself.

You gotta save for taxes.

This is a really specific thing, but if you’ve worked your whole life for the man (I had!), it’s a seriously hard transition to understand that that big fat check you got from a client isn’t all yours. The vast majority of self-employed income doesn’t have taxes withheld automatically, so that means you gotta do it yourself. Because come tax time, you won’t be getting a fun refund check (oh, how I miss the “I’m gonna go buy new shoes!” refund checks), but you will be getting a big ole income tax bill. I just automatically funnel 30% of every single check I get into a taxes savings fund. I don’t touch it. I don’t look at it. I don’t think about it. Then, come tax time (or when it’s time to for a quarterly estimated tax payment—which is something a lot of us self-employed folks have to do), I’ve got the bill covered. The 30% works for us and our current tax situation, but you might need more or less depending on your deductions, credits, and income level.

Saying “no” is hard. But you have to.

I’ve been very fortunate to be booked all year. But even with my crazy schedule, I have a really, really hard time turning away work. The truth is, as your own boss, you never know when the work will dry up, so it’s really friggin’ hard to turn away someone when they’re holding cash out in front of you. But after a particularly crazy over-booked summer, I realized that I had to learn to turn folks away.

computer email

It’s hard. But the truth is, if I took on every single request I got to do a design in three days (PSA: a good graphic designer is probably booked at least two months in advance, and you should plan accordingly or at least plan to pay for a rush job) or to write an article by noon tomorrow, I’d have lost my mind back in October. Plus, saying “no” to all the low-quality opportunities leaves you open to say “yes” to the high quality opportunities.

You’ll get all kinds of reactions.

The vast majority of reactions I got when I told people I was going out on my own were positive. They ranged from “good for you!” to “you are my hero!” But every now and again, you get the not-so-nice ones, too. I’ve heard my fair share of mentions of being spoiled and privileged (which, I don’t deny, I am privileged, but I also worked my butt off to get here). I also hear a surprising amount of well, everyone else has to suffer at a job they hate, why shouldn’t you too? Which I find positively ridiculous. And my personal favorite, folks who just assume because I don’t have a job I must not work. I guess people just assume I sit at home eating bon-bons and watching my stories all day? Granted, I’ve had more of those days as of recent because of pregnancy, but most weeks, I’m actually working longer hours that I ever did at a “real” job. Craig and I have a real two-income household—meaning we couldn’t keep up with our lifestyle on either income alone. So if I was sitting at home doing nothing, we’d have been out on the street months ago.

It’s still a job.

Yup. Even with all the benefits of running my own business, there are a still days I hate going to work. Granted, those days are few-and-far-between compared to how many I had back at my old gig, but they’re still there. There are still the days when I deal with stupid people and have to answer stupid emails and work on stupid projects—all for the sake of being able to pay my mortgage.

I know that “love what you do, and you’ll never work a day in your life” quote is a popular one, but I think it’s a load of bull.  The second that money is involved, it becomes work. Sure, it might be work that you enjoy and are passionate about most of the time, but when it’s your source of income, there will always be days that you don’t want to do your work, but you have to because you gotta put dinner on the table. And that doesn’t go away just because you’re your own boss (although, like I said, it is a whole lot less frequent).

Have you ever struck out on your own? Or dreamed of it?

Cassie is the founder and CEO of Wholefully. She's a home cook and wellness junkie with a love of all things healthy living. She lives on a small hobby farm in Southern Indiana with her husband, daughter, two dogs, two cats, and 15 chickens.

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31 Responses
  1. Mikki

    Im late to this post but I lost my slavery position last year in January and after a string of ridiculous interview processes (one of which included a cognitive test that I aced and EIGHT interviews) I opened my own business. I hired a smart and dedicated employee (me) paid her well, and never looked back. I have rough days like you mentioned but I do laugh and smile every time I get a new client, a payment, a repeat client, or a happy review. I love it. Also I am saving about 15 hours a week not traveling to work. From that the $4 a gallon gas does not really affect me. Gosh this is pretty good.

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