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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. Megan

    I normally don’t post many replies to articles I read but as I woke up this morning absolutely dreading work, practically in tears, I decided this is enough. I can’t do this until I am too old to walk. I’ve started research on becoming my own boss and breaking free of corporate slavery. You have inspired me Cassie. Thank you and I wish you nothing but the best.

  2. Love this post! I always get so interested to see how the other spoiled and privileged half spends their days 😉 (Totally kidding) Somedays I would like to work from home, but I also know myself and would go stir-crazy. I like office life, I like the routine of getting out of the house. I wouldn’t be disciplined enough to be successful on my own. I’d take too many “days off” for TV show marathons! 😉

    But seriously, good for you in finding what fits for you and makes you happy! Surprisingly, I have, too, in the office world of research administration and grants. Who knew I’d end up here and love it?!?

  3. SherryMarie

    I am new to your website, but quite enjoying everything I’ve seen. My husband went on his own 25 years ago. We had three little kids and the insecurity of not having that regular paycheck was hard. But I scrimped, and stayed home with my kids and raised them the way we wanted. No underpaid daycare workers for us. After a few years we had employees and we needed a draftsman, so I grabbed a book and started learning. Today we each make more per hour than we ever dreamed possible and are looking at early retirement.

    Two pieces of advice for those considering this. One is exactly what you said about the taxes. You NEED to set that aside every month. You can’t say, “Well, we’re getting paid for that big job next quarter. It will cover that.” If you do, you won’t sleep at night. And two; being your own boss means that when you have work (and thus money) you won’t have time to take holidays. And when you have time to take holidays, you’ll be worried that you should be out there looking for work, not spending money on frivolous trips. So be sure to allow yourself to take ‘holidays’, even if it’s just movie night or a weekend away from the kids, regularly.

    Good luck with your business. I wish you 25 years of challenges and success.

  4. I agree with the above post that I have always wanted to work for myself, but I am not sure what I want to do. I really have a creative streak that I would like to explore and see if I can make a job out of that.

    Thank you for sharing. You give me hope that one day I will be able to find a way to be my own boss and do what I love.

    1. Cassie

      One of the things that really helped me was understanding that it didn’t have to be just one thing. That’s the joy of being your own boss, you can do ALL the things you want to do. I narrowed it down to “graphic designer and food writer” for this post, but I do so much more than that. I’m a blogger. I’m a photographer. I have an Etsy shop. I’m a recipe developer. I’m a social media consultant. You can pursue all the projects you want to (and in fact, I think it’s a safer way of going about it—not putting all your eggs in one basket).

      Granted, when people ask me what I do, it takes about an hour to list out all my gigs. 😛

  5. Emily

    THIS. I think you’ve covered everything really well. I’m also in the process of striking out on my own and the creativity, energy, and inspiration is back… so is the stress of not knowing what my income will be from month to month, but I also find that I am spending less money because I am not as depressed or stressed as I was before. I am enjoying the simplicity I have been given right now.

  6. Boyfriend, AKA my husband, quit his job as an Engineer a year ago in October. I’m not a cussing woman but if I were I’d tell you that taxes are a B#@!#@$. Holy COW!!! That is one thing that has made me so grumpy being self-employed. It is truly awful. The first few times we had to be pay we almost died. We’ve gotten better at planning for it now at 15 months out but it was a huge learning curve. That for sure is the worst part of not working for the man, paying him all your dollars instead!

    1. Cassie

      The interesting thing for us is, our overall tax bill is actually MUCH lower than it was when we were both working–so we’re actually paying Uncle Sam a lot less now, but it just feels much more painful because I don’t have any withholding on any of my income. So I have to actually do the action of writing a check, versus it just automagically disappearing from my pay. Even though it’s the same idea, it hurts so much more this way. 😛

  7. Great post Cassie, I found myself nodding and agreeing throughout.

    I went self employed back in 2006. At the time I was single, had a mortgage but couldn’t tolerate 1 second longer in the employed role I was in. People had told me for years that I would make a great consultant in my field but I didn’t believe them … turns out they were right.

    In the last 7 years the only lean times I’ve had have been through choice. Last year I took 3 months out for foot surgery for example.

    One thing I would encourage people to do is network, network, network. This doesn’t come naturally to me but people need to remember if you are not in tough you are probably out of mind. Check in with contacts once in a while, you never know when something useful might crop up. Also if you are busy recommend others, they are likely to remember you did that in the future. Bank some Karma!

    And, yes …. never ever think the tax money is yours! I do the same as you, that money doesn’t exist to me but I know people who though it did then got micromanaged by the tax folks for years after!

    Life’s short, just do it 🙂

  8. Hi, Cassie! Wonderful post! Thank you for sharing. I recently quit my job as a full-time instructor of freshman composition at a state university to start a business of my own. I know absolutely nothing about running or owning a business, but I could not keep teaching (universities are more interested in retention than education these days and I am NOT on board with that particular educational goal). I, too, waited a few years before quitting, hating to give up the security of a job I had grown to dislike. My husband finally convinced me to quit; I had no time to pursue my dream as long as I was snowed under with grading stacks of compositions and research papers month after month.

    This past year has been a worrisome time for me in many ways, as I learn everything I knew I didn’t know about starting, owning, and running a business, as well as the things I didn’t know that I didn’t know! After a year of self-educating the ins and outs of business, I realized that I would never know everything at once so to urge myself to get started with my plan in earnest, I officially formed my business, an LLC, on September 23rd, 2013. Now I’m forced to finally get moving toward placing my product on the shelf, and learning as I go.

    You describe wonderfully the conflicting joys and stresses of self-employment in your post. Although being one’s own boss allows one the freedom of flexible schedules and such, the structure of being an employee has its benefits. As an employee with deadlines, I knew what I was doing all the time, as well as what had to be done, and by when it had to be done. Now I always wonder whether what I’m doing for my business is the right thing I need to be doing at the time I’m doing it. I’m insecure about my ability recognize the most important actions I must take in a given day. I am fortunate to have a husband who is employed, and who for now has a steady paycheck (for job security is a thing of the past, if it ever really did exist), so I have room for error (but I dislike errors!). Even though I have no idea what I’m doing 95% of the time, working for myself has rescued my spirit, which was dying a slow, painful death when I was working in the business of higher education.

    How exciting that you are expecting a baby! You and your husband are providing a wonderful environment in which to raise your child! You have a blessed life, indeed! Thank you for sharing and inspiring others to nurture their spirits, bodies, and minds.

  9. You are so right, it IS still a job. I’ve been trying to place my finger on that when I’ve had a few “off days” lately. You got it.

    I quit my full-time job in corporate marketing in November. This is my first year trying full-time freelance writing and editing. I was doing it PT for the past three years.

    Thanks for sharing your 1-year story!

  10. Thank you so much for this post. I’m in the position right now where I lost my job a while back. Instead of looking for another full-time position, I decided to start trying to work for myself.

    I took an entirely different career direction than I have been working on, so I’m in the position where I’m trying to build up my portfolio/resume.

    I always wanted to work for myself, but didn’t know what I wanted to do and when I would want to do it. I’ve had several jobs that I’ve always been unhappy with. When I lost my job, I figured there would be no better time than now.

    I’m not making any money yet and it’s nerve wracking, but I’m working hard. And my husband and I have no debt, so we are in a good position to do this right now.

    I agree with you, I’m not sure if I would be happy going back to an office job, so I’m trying not to.

    1. Cassie

      Related story: I was laid off from a job a few years back. And on the day I was laid off, all the other laid-off employees wer in tears, and I found myself with the biggest smile ever. It was my first sign that maybe the whole office thing wasn’t for me.

      Good luck!

  11. Thank you for putting this out here for the rest of us to read! Probably one of the more honest accounts of what working for yourself is all about. I’m doing a hybrid of this, I work for my parents, so I have the steady job, but I do have quite a bit of flexibility to do my own things.

  12. Great post! I love hearing your perspective on being your own business. My last day at my day job was Jan 31 of last year, so I’ve also been own my boss for the past year. I totally agree that there will never be a “perfect”time to quit, and I’m so glad I made the leap when I did. I couldn’t agree that sometimes it’s still a job.

  13. Rashada

    I am in a different position then you.
    I have a part-time job where I have a boss, but my job (scanning, cataloging and otherwise organizing 20+ years worth of photos he’s collected over the years) is something with no immediate deadline. We occasionally have part of a collection from someone on loan, so then it does need to be done immediately so it can be returned.
    Otherwise though, I can go into the office whenever I want, which is awesome when you’ve got 3 kids. But it’s also not awesome when you are unmotivated to get up and go and your husband also has a job which allows for extreme flexibility.
    I think I need to just set 2 or 3 days a week on which I have to go unless one of the kids are sick.

    I’ve very envious of your ability to keep yourself on task.

  14. Working for myself is something I’ve debated for awhile now. I’m nervous to make the leap because 1) the cost of living here sucks (our rent is pretty much four times what my rent was in Indiana!), 2) this area is oversaturated with marketing agencies, tech companies, and freelancers, so I would really need to stand out to make a living here in town, and 3) the confidence in my work abilities is really, really low right now, where I think I suck at pretty much everything and well, clients wouldn’t want to hire someone feeling so down!

    I think about changing this a lot, though, because honestly, I hate my job and I hate that I’m wasting my life here. I have learned that corporate America is not for me and I don’t do well playing the game at all!

    Your story is inspiring to me, too. I am trying to get my self-esteem back in check before I make any huge leap, just so I have the confidence in myself as a developer again and the confidence in myself to actually make a change. I’m happy you are much happier where you are right now.

    Happy one year quit-a-versary!

    1. Cassie

      The dwindling confidence thing was one of my biggest reasons for leaving my job. Even if you know you are good. Know you are talented. Know you’re successful, you can only take so much negativity, criticism and tear-downs before you start to believe it yourself. And I started to believe it. I am a multiple-Webby-award-winning designer, and yet I would come into work everything thinking, “Wow, I really suck at this. I’m going to be stuck here forever. No one else will ever hire me.” And it just keep getting worse and worse. To the point where I was trying all kinds of different degree programs and career paths to try to find something that I didn’t feel like I sucked at (none of it took, because the truth was, I didn’t suck at what I did).

      Now, my clients really appreciate me. Not only because they like what I do, but because I’ve given myself the power to align with clients who appreciate my work and my style. I’m no longer forced to work on this one account with this one client who things I’m a weirdo and thinks everything I do looks like puke (real world example, there). I’m in control of it. And it’s helping build my confidence back.

      1. “Wow, I really suck at this. I’m going to be stuck here forever. No one else will ever hire me.”

        This is EXACTLY how I feel right now. EXACTLY.

        I’m glad I’m not the only one who has felt this way, and it’s good to know that it’s something that can be changed. Thank you for your reply, it has helped me a lot this morning!

  15. Erin

    Hey Cassie! Thank you for writing this. I’m seriously considering striking out on my own as a freelance writer/editor and I’m really battling the “what ifs.” What if I can’t make any money? What if I find myself missing my office job? What if I am throwing my career in the toilet by not climbing the corporate ladder? What if I’m judged? There’s a lot of noise in my head, but working for myself is something I really want — at least I think I do. Your first point, “there will never be a perfect time to quit,” really resonates with me. I’m a perfectionist and I keep waiting for the “right” time to quit corporate America, but I think I need to work on accepting that there will be bumps and doubt and fear along the path, and there’s no way to pave over those things with planning.

    1. Cassie

      I struggled a lot with the what-ifs ahead of time, too. The thing that really helped me: I kept reminding myself that I can most likely, always find another job. It might not be my dream job. It might not make a ton of money. Heck, it might be running the drive-through at McDonalds, but with my skills, education, and connections, the chances are, I could always find something. Maybe that’s naive in this job market, but it helped me softened the what-ifs.

      1. HeyBeckyJ

        Slightly off-topic, but I have found that being confident that I’d be able to find something else job-wise is be incredibly freeing in ANY job move. I work for a very small company that reports to a huge parent company. My skill set doesn’t easily translate into being able to work for myself, and I don’t really have the desire to do that. But feeling confident that I’m not stuck here is liberating and gave me the guts to request a more flexible schedule when my kiddos were born, to ask for additional responsibility when the opportunity arose, and to propose slightly riskier ideas. I took me a long time to believe in myself (as cliche as that is), but I think it’s key to any career – corporate or self-employed.

        Congratulations on your quitiversary! I enjoyed reading about your transition!

  16. Cassie, I just want you to know that you are my inspiration. I am also a graphic designer and dream of one day quitting corporate America to freelance and be my own boss! I’ve worked in a small agency environment as well as in-house at a giant corporate company, and I’ve come to the realization I’d like to work for myself, like you. Thank you for these posts and your honesty on the topic! They keep me hopeful 🙂

  17. I think you managed to accurately portray the pros and cons of being self-employed. I owned a little pizza parlor for 13 years. When I sold it, I was ready to no longer work for myself. Now, several years later, I’m feeling that urge to make the move back to self-employment. It’s scary to think about giving up the security of that weekly (or bi-weekly) pay check…but I find myself absolutely dreading going to work…looks like I have a decision to make, doesn’t it?

  18. This is great and I’m sure it will help others who are in similar situations as you. I’m sorry if you’ve already mentioned this, but what are your plans for child care? Will you have an in-home nanny? Just curious. 🙂 Thanks for sharing all the details of your transition and I wish you the best in your next year!

    1. Cassie

      Our plan is for me to take off a maternity leave for at least six weeks, and then I’ll go back to work part-time—mostly doing my work on Craig’s days off. Although, we do have my parents nearby, too. And they’ve offered to do baby-watching so I can work, too. Then, come late-fall, Craig’s job ramps down (his work is seasonal), so I can ramp back up to fuller-time while he’s home more.

      Although, admittedly, this is all the plans of two first-time parents, so who knows how things will actually work out once Baby J is here. 🙂

      1. Jen in SC

        I was going to ask the same thing about child-care! Every baby and every family/situation is different, of course….but my unsolicited advice as a mom of 2, trying to work PT from home with no childcare: please get childcare. At least some, regular, you-can-count-on-it childcare. I promise it will be more helpful than you could ever imagine. You’ll need times where you can completely concentrate, or make calls, or whatever, for more than whatever 30 minute or even 2 hour nap window that baby might want to give you that day.
        Very good and interesting post! I am so glad for you that you’re enjoying the self-employed gig. More power to ya, lady! 🙂

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