You Don’t Have To Quit Your Job and Start Your Own Business To Follow Your Passion… Advice From A Former Freelancer

May 21, 2013

Confessions of a former freelancer


Chances are if you’ve been outside of a cave with reliable internet access for the past two years, you’ve picked up on the general “lifestyle design” buzz that has been telling us to quit your job, leave your cubicle and start your own business. Words like “freelancing,” “location independence,” “anti 9-5” and “cubicle renegade,” are thrown around as if to wake the sleeping masses with a gallant call to action to free the oppressed, the sheep employees of corporate life.


I had my own business and recently chose to leave freelancing  in order to work in one of those “damned cubicles.” It’s the choice I needed to make and “going corporate” has been totally freeing.


Of course, with every craze- there are two sides to every coin. Many of my friends and colleagues have quit their traditional jobs and decided to strike it out on their own, to them, I have nothing but respect to convey.  They’re forging new trails off the beaten path and are valuable resources for those who dream of doing the same but need some guidance.   Some of my favorite bloggers have started their own businesses, but they made calculated moves and forged a plan.

What I will say though, is that beyond the wise trailblazers that have made big decisions and long term plans to shake up their careers, there are a dozen others who tout themselves as career renegade gurus or people that want to make a quick buck publishing books on the “passion craze” or are living off Google Adsense and affilate sales selling what people want to hear, not what they need to hear. “Quit your job and follow your passion” is much sexier and gets more attention than someone who touts a message of looking inward for fulfilling work in the life they already have.  Apparently even when it comes to careers,  the “Eat, Pray, Love,” idea of leaving it all behind and starting fresh seems so exotic, so enticing and it sells more career books than more traditional advice.  Heck, it even sounds better than “work your way up the corporate ladder,” but what they fail to mention is that sometimes, when you start over, you start from the bottom..many career shifters aren’t prepared for that.


Many “get rich online” and “follow your passion” gurus are rich simply because they’re talking about getting rich online/quitting the cubicle, not because they will help you make a plan to build a successful business.  Some (not all) “anti corporate” heroes make money because they sell you on an idea, not on a plan, and it’s a very profitable and popular idea.


I had a freelancing business for nearly two years and over time, I realized that while I loved the work, I didn’t love the lifestyle.   While freelancing provides unique freedoms and there are plenty of resources for freelancers to succeed, it does not always afford autonomy over your own work, which is one of the biggest selling points that many of the “quit your job” passion-fuelers base their claims upon.  If you want more control over your work, more freedom and more cool projects, trust me- freelancing isn’t the sexy catch all people claim it to be. It’s rewarding yes, but is it the only answer? Nope!

When it comes to starting your own business- the gurus seem to imply that having your own business is the ultimate freedom.  While anyone would assume there’s a downside to working for yourself,  it’s appealing to sell “hard work=freedom,” but shaky ground to tell potential business owners, Etsy sellers, potential nomads and possible freelancers that “sure, you can work from anywhere at whatever hours you want, but you’ll always be working!”

You start your own business to create more freedom- but it’s easy to feel as if you’re more tied to a desk and sometimes feels like you have even less control over the work you produce. If you’re not prepared for overdue invoices, clients that cancel work midstream (without pay) or have the savings in place to cover your tush during slow months, you’ll quickly see the dream evaporate.  My experience with running my own business was at times challenging, but it was very rewarding for the bulk of it- but as I grew older and my life changed (for the better) my needs for what work would be changed…and I found I actually found the freelancing lifestyle less and less appealing both personally and professionally.  Of course, that epiphany that I wasn’t satisfied was a very uncomfortable place to be-  while everyone else seemed to be wanting to quit their traditional  jobs, I wanted to find one.


I sensed over time that just because you’re passionate about your work, it doesn’t mean that creating your own business around it is the best way to create a career you love.



I recently read the book, So Good They Can’t Ignore You:  Why Skills Trump Passion in the Quest for Work You Love by Cal Newport, Newport discusses the plight that impacts many people that “follow their passion.”  Some hope that starting their own business will finally lead to fulfillment (because they’ve been told it will), but end up chasing a mirage. The problem isn’t the passion or the idea that their work doesn’t align with their passion, it’s a lack of other factors that make work truly rewarding- autonomy, value, freedom and a few other tangibles.   Many employees feel powerless in their jobs and their lack of fulfillment isn’t a lack of passion, it’s a lack of control..sadly, many don’t realize that “striking it out on your own” doesn’t always lead to the types of control you want, nor will “passion” be enough to make you happy, pay your bills or fall in love with your work.

I had been struggling with the decision to get a “job” for a long time (nearly a year) and had doubted my decision to throw it the towel on my freelancing business to work for an employer.  At times, I felt like a fluke, like a quitter, that this magic elixir of being self-employed didn’t do what it was supposed to do- lead to full-time bliss for part-time work.  I began to realize that people with a traditional job could be happy, they could be fulfilled and they didn’t have to strike it out on their own if they knew what to look for, what to demand of themselves and if they put in the time to find an employer who resonated with their values.

After months of stomach aches, indecision and feeling like a “passion failure,” I finally, and excitedly, accepted a job offer to do social media freelancing for one client (an employer) instead of keeping up the juggling act of several.  I realized I loved the work but needed it in a different context-  the “freedom” of freelancing began to feel claustrophobic, as I became a hermit tied to my computer all day… not at coffee shops, not at bookstores, by myself, in my home office.  I wasn’t meeting new people, I was working all the time and I found that there was a disconnect between how I viewed my work and what my clients wanted (or heck, were willing to pay).  I was growing weary of invoices months overdue (whereas credit cards and car payments always arrive on time) and my skills and abilities in the social media field began to feel stagnate as I began doing whatever would pay the bills, not what would advance my career.

Freelancing isn’t bad- it’s just not the magic pill everyone expects it to be.  Following you passion or hating your current job isn’t enough to be successful in your work.  Passion fades but commitment to a craft does not.  You may find that the way you execute you work (like the company you work for or the position you have) diminishes over time, but your love, or your calling for the work itself stays strong.  Be wise about what you quit on- be sure if you love the work, not the job, you’re making a solid choice on how to carry out that work, not just blindly “hate jobs.”  There may may be consequences you don’t intend (like becoming a hermit) or you may find it’s helpful for a time, but not a permanent lifestyle.   It helped me get through graduate school and even lead me to snag the job I have now, but as with anything- it has a time and a place.

Before you go all in and quit your job, make sure you’ve done your research, saved up an emergency fund, built a solid client base and you have the heart and hustle to make it work. I’d also recommend you do a serious assessment of your current career and your actual job to see why it lacks and if the things you’re missing from your daily work would actually be solved by flying solo.  If you’re valuable enough to your company, they may be willing to work with you- if not, be brave and find a company that will let you do work you love in a context that addresses your needs.

I don’t have any beef with freelancing, but I do worry about people that chase the freelancing mirage hoping it will somehow fulfill a void in their life.  When I was a broke and overbooked college student, it was perfect for me. I could work from class (yep, did that!) or late at night, from my phone or from NYC if I so chose (and did).   A year after graduating though, I realized that personally and professionally, I wasn’t able to run a business and advocate for the intangibles you can get from the right workplace- colleagues, benefits, a steady paycheck, professional growth, work you love and a cause you believe in.


So, after running a solid freelancing business for nearly 2 years that I should have loved, I got a day job and I LOVE it.  I struggled with the idea that I was “quitting the dream” for over 6 months, but now feel solid in my decision and proud I could own up to what I really wanted, not what I thought I should want.

Sometimes, walking in your truth means you’re an iconoclast among iconoclasts- take ownership of your choices, and do work that you love, even if people don’t get it.


Love from the 9-5,



P.S. Lots of love to all of my freelancing friends that supported my decision and helped talk me through it without judgement or calling me a “cubicle slave,” (ha!) you all are amazing and I wish you the best of luck as you build your own successful businesses.  To the people that didn’t understand my choice, good luck to you too! haha!


P.P.S.  This blog (and will still get all the love and attention it deserves and I will still offer Rockstar Blogger Coaching– but the bulk of my freelancing work via Cake Mix Media  has been phased out to refocus on blogging, social media management in my new role & coaching.


25 comments so far.

25 responses to “You Don’t Have To Quit Your Job and Start Your Own Business To Follow Your Passion… Advice From A Former Freelancer”

  1. Seriously, are you psychic? My post today was on passion vs. money.

    I think I’m going to recruit you to give me some therapy when we meet at FitBloggin next month. I am *so* where you were at and tipping over to the desk day job side pretty damn quickly.

  2. Andrea says:

    I’m so glad you have found a job that you love and the stability you needed! I love running my business and working from home but I definitely don’t think it’s for everyone. I have also sworn to myself that I’ll never be one of those people who profits from selling a dream to others – yes, it’s possible, but that doesn’t mean it’s always the right move for every person.

    Being true to yourself is more important than anything else you can do in this life, my friend, and you are doing just that. I can’t wait to see where your path leads because I know good things will continue to come your way!

    • Shannyn says:

      Thanks Andrea- and when I talk about freelancers that built a business authentically and kick ass, you are part of that group. When I was freelancing (even now that I’m not) you helped me so much! You=awesome. 🙂

  3. I don’t mind my 9-5 at all, and I don’t think I’d be as well equipped to break off on my own. I need work/life balance and that’s not something that is usually granted when you work for yourself. I know myself, I’d work until all hours!

  4. Sarah says:

    You’ve given some great advice here about what potential freelancers should think about before they take the plunge.

    I personally think you’ve done a brilliant thing Shannyn. You’ve got a passion – running – and you’ve found a great job that fits around that…. seems like a no-brainer to me!

    Freelancing can be the most amazing thing for some people at the right time in their lives but for others it’s definitely wrong. However, I can definitely see you commencing your freelance activities later on in your career as you definitely have the flair for it.

    Enjoy the new job and keep us updated with your endeavours. Sarah

  5. I just got laid off with a 6 month severance package and my former company paying for Cobra benefits for a year. Lots of people has asked me if I’m going to take the opportunity to turn my blogs into a business, start my own company, etc. And for me, the answer is No. Always has been and always will be.
    My brother owns his own business and loves it. I love the steadiness of a paycheck, of knowing what my hours are (or at least being able to be off the clock when I need to be), paid vacation, and great benefits. I also love going in to the office and socializing with other people there.
    I think everyone has to make the decision that is best for them and their life, at the point they are currently at. Freelancing was great while you were a student. It wasn’t working now, though, and that’s okay.
    I am very happy you found a job you love and feel great about doing.

  6. Sounds like you made the right choice for yourself! Here’s to the security that comes with being an employee. 🙂

  7. Michelle says:

    Great post! My post today is the opposite of what you wrote today 🙂

    I’ve worked the 8-5 ever since I was 16, and I need a change. Hopefully freelancing will do me good.

  8. Mary Ann says:

    I am so glad you wrote about this!! I may reference you in a future monthly blogging business post on School of Moxie. Your decision is a sound one and you should be really proud of it! I love your context, that there is a time and a place for everything. Perfectly put! 🙂

  9. Jessica says:

    Congrats on the new job! <3

  10. Bailey-Eileen Dexter-Parr says:

    Congrats! Life is what you make it.

  11. Excellent words of wisdom! I’m a full-time freelancer, and I’m also the first to tell you that this lifestyle is NOT for everyone. Yes, I make my own schedule … but I also work alone (which is tough for an extrovert!) Yes, I get to pick-and-choose my clients … but I also deal with an erratic income. In other words, there are plenty of pro’s and con’s … it’s not all butterflies and rainbows. And climbing a career ladder is the same. There are pro’s and con’s, and it’s too simplistic to say that one lifestyle is inherently “better” than another.

  12. Kristin says:

    Great post! I think you’re really hitting points a lot of people forget to think about before going completely freelance. <3

  13. Hey Shannyn: Great post and your cautions are very important. Most people are ill-equipped to run their own business. And this is a lot of hard work and very time consuming. It is not for everyone. Your warnings near the end of your article are especially noteworthy.

  14. eemusings says:

    Glad you found that dream job!

    Completely agree – the freelancing I do isn’t all fun and games – it’s a rare freelancer at the stage where they can pick and choose only the projects they truly love.

  15. Just happen to stumble accross you today – and this could not have been a better post for me to read. I have really been struggling with my job lately and torn on “quitting”, although I have not been thinking about “freelancing” this post was very eye opening for me – thanks for your feedback from the other side!

  16. Hope says:

    I couldn’t have read this post at a better time. I took a position with a marketing start-up last July, working for a woman (it’s just us two) who I’ve worked with for several years…she’s a mentor to me. While I’m learning SO much valuable information, I’m finding that freelancing…well, I just don’t know if it’s for me, and I’ve been looking online for stories like yours, where you’ve found that corporate life IS for you. I do like my job, but sometimes the being alone (my boss is in and out, constantly) and it’s almost…dare I say…too much freedom? I find that I do better with in a more structured environment. Anyway, just wanted to comment. Thanks for writing this!

  17. Do or Debt says:

    Awesome post! I just recently got a job as well, and I am so thrilled! I was working as a contract employee for so long, and I now I get paid to be an employee for an org I love. It all comes down to choices, preferences and how you want to spend your time and make your money.

  18. Michelle says:

    Thank you for the amazing post! I am beginning the transition to eventually running my own business in the next couple of years. Something must be in the air today because there were several posts talking about the pros and cons of working for yourself. I have worked for other people for a long time and am looking forward to being my own boss. However, I acknowledge that I’ll probably work in an office again at some point in my life. Congratulations on the new job and doing what is good for you.

  19. Congrats for finding a job! I can see how you will love more stability. I think most folks go about the desire of freelancing after working at their job for a number of years. Everybody gets bored after a while and after one too many years of no growth, doing something on your own is an inevitability.

    Perhaps by going in reverse, you’ll end up loving a job for much longer since you know what’s waiting for you as the alternative? I did 13 consecutive years and must say my fire started fading after about the 11th year. Let us know how your views change over time!

    Best, Sam

  20. As a freelancer I can totally relate to everything you said. I go back and forth on whether or not this life is for me. I do crave a steady paycheck, health benefits, and a 401k, but I also like a flexible schedule and working from home. I walk that line almost daily about what to do for my future.

  21. Danielle says:

    Great post! I’m happy as freelancer, but I caution my clients that there is no right way to go about this. Freelancing isn’t for everyone, and there is no reason to feel guilty about it. I even wrote a post on keeping your 9-5 job. Skillset IS very important. Using your strengths and being self-aware is important to job satisfaction as well.

  22. Tiffany Sun says:

    Best quote I learned from you:

    “Passion fades but commitment to a craft does not”

    Everyone has their own passion, but how many would commit to it and make it a living? Free-lancing isn’t for everyone…I believe it’s all about your personal drive to work hard and keep at it. And you definitely are a good role model. 🙂

    How did you find out freelancing was the right path for you though?

  23. Utrecht says:

    Wonderful items from you, man. I’ve take into accout your stuff previous to and you are simply
    extremely great. I really like what you have got here, certainly like what you’re stating and the way wherein you are
    saying it. You’re making it enjoyable and you still care for to stay it
    wise. I cant wait to learn much more from you. This is actually a tremendous


Get Updates Via Email

Join The Frugal Beautiful Update List!
Get Posts Sent To Your Inbox...subscribe below!