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Ditching Your Job: A Reality Check


A recent Associated Press story noted that Americans’ job satisfaction has fallen to a record low. The reasons for the unhappiness include:

  1. Fewer people viewing their work as interesting.
  2. Incomes lagging behind inflation.
  3. Rising health insurance premiums taking more out of workers’ paychecks.

Even a brief reading of FreelanceSwitch will show that we view our work as interesting. So interesting, in fact, that it can take over our lives. Case in point: NC Winters’ “Freelance Freedom #133,” where our hero is having an argument with the houseplants he’s watering. And the plants are winning.

The notion that the plants might emerge victorious has our hero’s wife quite worried, but she may well be in the minority. Why? Because there are millions of other people who crave interesting work, and, hey, that boss-less, higher paying life of a freelancer sounds pretty nice.

Now, here’s Martha with a lot more water than our freelancing hero just used on his plants. And it’s ice-cold, here it comes – splash!!!

I’ve watched a lot of business ventures over the years. And I’ve seen more “train wrecks” than I care to count. Some are outright business failures. Others just withered away.

Then there are the ones that may have been successful, but that success came with a high price. We’re talking divorce, family dislocation, bankruptcy, health problems, legal problems, the list goes on.

In short, self-employment as a freelancer is a lot harder than following your dream. Or doing what you love and knowing that the money will follow.

Rather, freelancing is hard, serious work that demands considerable talent and savvy to succeed. Blogs like FreelanceSwitch can provide you with the knowledge that may help you succeed, but you still have to do the work.

How I wish I’d known this a decade and a half ago.

That was when I followed my heart and started a book publishing business that was based on my passion, bicycling. I ended up losing my life savings and then some. What caused this to happen?

Well, for one thing, I didn’t have the business knowledge that would have set the alarm bells ringing in my head and warned me away from this ill-fated venture. So I went ahead with it anyway.

It is said that experience is the best teacher, and I’ll admit that I learned a lot from the failure of my publishing business. But those lessons came with a high cost.

I lived on a slender shoestring for years. At one point during the summer of 1997, I was working two jobs in addition to my fledgling Web design business.

For three and a half years, specifically, May 1997 to December 2000, I worked a six-day week. And the purpose of my Saturday bicycle shop job was to generate enough money to buy the groceries.

The shop job was also instrumental in the turnaround of my attitude and my Web design business. I had been pretty down and depressed since the book business went bust in 1995, and I was too broke to afford a therapist.

So the boss at the bike shop became the one to talk to. And while we were talking, I was learning how to fix bikes like a professional mechanic. Now, I thought I knew how to work on bikes before, but Bob showed me how to do it the right way. And that was his way. Heck, he’d been in business for almost two decades, and people came from far and wide because he was such a good mechanic.

And since he had all of that business experience, I figured that the shop job would be a good way to learn some things I could apply to my own business. So I asked Bob a lot of questions. And after I got off work, I’d go home and write down the answers.

In short, I became a committed Student of Business.

The bike shop job also required selling, which was my Number One Pet Peeve. But I had to do it in order to keep my job, and, hey, I do like to eat regularly. So I watched how my coworkers sold stuff, I watched how Bob did it, and I figured that every customer who walked through the door presented an opportunity to practice my skills.

During my final two years at the shop, I was blessed with a shy coworker who preferred to stay in the back and fix the bikes. “Thanks, Mike,” I thought. “I’ll handle the sales floor.”

That increased sales practice was great. I’ll admit that it didn’t help the shop that much – Bob was getting out of the business and didn’t want to stock much inventory. But it did work wonders for my little studio.

Fast forward to today. I’m still in business. My studio is profitable. Unfortunately, the bike shop building is just an empty, boarded up shell. Bob kept the building after he closed the shop in December 2000, then he decided to sell and finally did so in 2006. The new owner has yet to find a tenant.

I feel lucky to have survived the decade since the bike shop closed. I’ve become acutely aware of how high the price of success – and failure – can be.

Since we’re closing in on the end of this post, it’s time to share four lessons learned:

1. The Real World has much to teach us. Although much has been said about how much one can learn online, I learned a lot in that little store. Much of what I learned had to do with selling, one-on-one to real people. (And if this introvert can learn how to sell, well, anyone can!)

2. Don’t just mind your own little store. Be a business and economic trend-watcher. Changes in the business climate can sneak up on you, overwhelm you, and then take your business down. In this particular instance, the shop’s business really turned down in 1996. This was due to a slowdown in U.S. bicycle sales during the mid-1990s. (Remember how well the sport utility vehicles were selling back then? We saw a steady stream of them on the street outside the shop.)

3. You can only cut costs so much. The owner responded to his business downturn by cutting the fulltime staff, then covering most of the hours himself. He hired part-timers (like me) to cover the remaining hours.

Business continued to decline, so the next thing that got cut was marketing. Then the inventory dwindled. The place needed a good, top-to-bottom cleaning, but he couldn’t afford to hire a service to come in and do it. And that job would have taken too much staff time for us to do.

While the repair work was still good and the service was friendly, the dirty store and the empty shelves told another story. So people took their business elsewhere.

4. Don’t just work in your business. Work on it. During the three and a half years that I worked in the bike business in Tucson, seven shops disappeared and only two new shops opened. I notice that the newer shop owners were more business-oriented. While they knew how to fix the bikes, they also knew their way around a business plan and a spreadsheet.

After my bike shop job ended, I stopped by one of the newer, more business-oriented shops. I noticed that the shop’s most recent profit and loss statement was posted on the employee bulletin board. While I couldn’t read the numbers, I was impressed with the fact that the owner cared enough to educate his people about that part of the business.

This particular owner was a lot like my boss. Doug was a good mechanic, but he noticed that the bicycle business was becoming more marketing- and merchandising-oriented. So he moved his store in that direction. He was also quite motivated by what was happening to the stores that weren’t making the shift.

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Martha Retallick is a freelance designer and photographer in Tucson, Arizona.



  1. PG Arijit Das

    Hey! very creative thinking is applied while writing this post…. I highly Appreciate its writing!

    I liked the fourth point – “Don’t just work in your business. Work on it.” and i’m really agree with it!

  2. PG dootzky

    True. Freelancing is often a lot harder then regular lazy 9-to-17h office work most of people is used to.

    Freelancing is hard work.

    Good article.

    Keep it up,
    cheers from Serbia, Europe!!
    dootzky

  3. PG Inside the Webb

    Freelancing is not a profession for everyone, and I think that’s clear right off the bat. You need to be a self-starter, have the motivation to keep yourself going even through down times and always be looking towards the positive future.

    I find that freelancing has released me from the shackles the US government has tried to put me in with the college life and 9-5 rat race, and although I need to put in more hours weekly than a normal job, my happiness rating is much higher than what I would presume it would be in a regular job.

  4. PG John Wang

    #4. Don’t just work in your business. Work on it. – This is by far the hardest part for most people during transition. Primarily because they’re used to just doing their job and not all the other work necessary to actually run a business, ie. Accounting, Marketing, etc.

  5. PG Reed Botwright

    I’ve used my experience from college, from working retail, and from watching other businesses succeed or fail to keep my business going. And it doesn’t hurt to have an amazing support network and great partners.

    And don’t compromise on quality (especially when it comes to customer relations). This will allow your business to build something up over time.

  6. PG Anne Wayman

    I think more people can be freelancers than most of us who do it suspect.

    Self-starting? Getting up to commute is one of the ways I learned not to.

    Talent? It’s hard to get worse at something you practice.

    And yes, you’ve got to pay attention to the business side too, but there is a ton of good info out there.

    I’m watching a young freelance writing friend of mine make good use of the marketing and business info from the Small Business Admin… who knew it would work for writing.

    Courage? Lots

    Savings? Sure helps ;)

  7. PG Joe

    Agree with previous comments about point #4. The transition from ‘just doing your job’ to maintaining a successful business can be rough. It’s quite rewarding though once things start to click.

  8. PG Nina

    IMHO, I always figure, if there’s an industry dedicated to something, it’s probably a little more complex than having the attitude of “I’ll figure it out as I go along”. People do this a lot, thinking they can figure out something quickly when experts take years to learn it. It applies to business knowledge as per your article, but is relevant to creative services from the other/client’s perspective too (isn’t it better dealing with clients that know and respect design/writing/web development etc, rather than coming in with unrealistic expectations or thinking they can do it themselves easily?) At times you may get lucky and succeed by figuring it out as you go, but it’s better to research and gain knowledge before taking risks with life savings and dreams. It also shows respect towards the people who know what they’re talking about. ;)

  9. PG Guerilla Grafix

    Great Post. It’s always important to ’study’ other businesses and business models to see what does and doesn’t work in particular industries; you can also take bits and pieces from each of those business models and apply it to your own. Thanks again for the post.

  10. PG Just...B

    Good post and a nice little reminder of things I need to work on. Getting a better grasp on the business side of things will undoubtedly help me now and in the future. I find that I’m already becoming more aware of things that I need to improve upon rather than shy away from them which will do me little good.

  11. PG Dwayne Phillips

    Thank you. Finally some one writes about the HUGE pitfalls in quitting your job and starting your own business doing what you love. I have two brothers and one brother-in-law who went off to “do what they love” under the promise that if you just do what you love you will succeed. All three went into bankruptcy. Thankfully, two of them have recovered in one way or another. Having a business, even if it is doing something you love, is no easy.

  12. PG alfon

    freelance job is not easy but i mean we can’t do something. The best openmind to be a freelance is skill and Creativity

  13. PG Arleen

    The thing to consider when you venture out on your own is what kind of Health coverage will you have and even Business Coverage if you decide to get a partner.

  14. PG Pinpoint Benefits

    I find that freelancing has released me from the shackles the US government has tried to put me in with the college life and 9-5 rat race

  15. PG Reed Botwright

    @Arlene
    What’s great is becoming a freelancer/entrepreneur in a country with Health Care, like Canada….

  16. PG Mark Buckley

    Being successful as a freelancer involves hard work, bravery, luck/ timing. Working for yourself is not for everyone, but when it works, you feel pretty fortunate that you are not sitting in a cubicle somewhere being told what to do. I do put more hours in then if I were an employee, but I chose a field of work I find interesting. I don’t stare at the clock waiting to get out because its my business and it stays with me 24 hours a day. As an aside, I am amazed at the number of unprepared people who start a business by leaping before looking at all that is required.

  17. PG George

    I am still struggling to quit my job. Any idea on how to sell an ebook?

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