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Lessons After Two Years of Freelancing

Robert Janelle

I was updating my LinkedIn profile the other day and couldn’t help but notice that under the “Independent Professional” heading was the time stamp: 2 years.

Has it really been that long? It sure doesn’t feel like it, but it gave me pause to sit back and think about my career so far and what lessons I’ve learned that can be passed on to others.

Like most people fresh out of college, I focused all my energy on finding the 9-5 staff job. Problem was, returning home from a unpaid newspaper internship in another city, I barely had enough money to put postage on resumes, let alone gas to drive to job interviews.

It was a few days after my return that I woke up to my phone ringing. It was my editor from the out-of-town paper. Something related to their coverage area was happening near me and… could I cover it?

Needless to say, I jumped at the chance to keep my name in print while looking for the staff job and some money for food was also more than welcome.

The boost in pride I gained from that one-off assignment soon faded, though, as the envelopes I’d been mailing out stuffed with cover letters, resumes and writing samples weren’t generating any interest from HR departments.

So, deciding to take advantage of contacts I’d networked with, I cold-called the editor of a trade magazine I’d met a year earlier. Turned out he was swamped with work and assigned me several articles on the spot.

Keeping in touch with the network proved invaluable since I’d be randomly contacted by these clients over the next few months with more work.

There’s no shame in being a weekend warrior

Even though I’d taken a night job in a call center to help pay the bills, I’d decided the quest for the 9-5 was a waste of time. Freelancing was what I really wanted to do.

But there’s a weird feeling I’d get now and then. I’d be looking in the mirror, usually adjusting my tie before going to interview a source and it would hit: I’m a fraud. I’m not a journalist, I’m some dork who works in a call-center and sometimes plays dress-up.

At least, that was until I started specializing in covering the technology sector and was being sent out to interview a lot of start-up entrepreneurs. Through interviewing these folks I often learned that despite having fancy business cards with CEO after their name, many of them had to take on other jobs while waiting for their businesses to make a profit.

That’s when I realized that I was far from alone. There should be no shame in the entrepreneurial spirit.

Don’t discount the job board

After abandoning the search for a staff position and focusing all my job search energy on freelancing, my college’s job board became significantly less interesting.

Pretty much every posting was for a full-time job, usually requiring the successful candidate to relocate to the middle of nowhere. But, for reasons unknown to me, I read through every single posting (still do!)

Then it happened: a local trade publication focusing on the technology sector was looking for someone to do a one-off article. I immediately fired off an e-mail and received the assignment.

Getting a single piece of work wouldn’t seem like a big deal — except that it led to a monthly column along with writing features now and then. Plus, it helped me find my niche — I now refer to myself as a freelance technology journalist.

Get out and do it

One of my favorite things about freelancing is that I’m allowed to live on what I feel is more natural sleep cycle for me: passing out between 4 or 5 a.m. and waking up at 11 a.m.

Now, the neat thing about staying up late and not sleeping much is that around 3 a.m. or so you get crazy ideas for projects and anything seems possible. It was on one those nights I discovered a really cool new blog called Freelance Switch. In my sleep-deprived state I figured, hey, maybe I can write for them.

I clicked the contact link and wrote an e-mail proposing a column (I think my original suggestion was “slacker productivity”). Not realizing the site is based in Australia and it was 3 p.m. for the editors, within ten minutes I heard back from Collis and Cyan and we bounced ideas for posts back and forth until I fell asleep on my keyboard. A few days later, I was a contributor.

Put fear aside and just do it. Otherwise, nothing is going to happen.

The most important lesson

To end off, I’d like to share the most important lesson I learned in these two years: If the 9-5 club doesn’t want to let you in, forget ‘em!

If you’re truly passionate about a career choice, do not give up just because of a seemingly endless string of job interviews that lead nowhere. Forget the hiring managers and market yourself directly to the clients.

Even if the freelancing lifestyle isn’t for you, it’s still a better way to get your foot in the door than sitting around listening to the phone not ringing.

Leave a Comment
  1. Robert,

    Thanks for your encouraging words! I wholeheartedly agree with your remarks on fear: lose it! After hesitating for a couple of days, I went and talk with the chief editor at RIT’s student Reporter magazine about an idea for a technology column (I’m an IT graduate student). I gave her the link to my old blog and, incredibly, she replied within a couple of days with my first assignment! I started writing for them recently.

    When I finally choose to go the freelancing way, I’ll follow the same modus operadi: fear out, confidence in!

  2. Robert, thanks for the great article.

  3. I too finally shut my computer at 4 am and wake up 11 am, always seemed to be those wee hours that exactly as you put it anything seems possible. One of the biggest things about being a freelancer is as cliche as it sounds, you are free to do whatever it is you love. That to me is the most rewarding part of freelancing.

  4. Now THAT was a great and inspiring post! I’m a full-time freelancer of just over 4 months, quickly coming to the end of my severance from when I was laid off, and battling with the notion of having to get a part-time job for now, until business grows. Thanks for your encouraging insights and advice!

    Terry

  5. “Put fear aside and just do it. Otherwise, nothing is going to happen.”

    Love that bit because it is so true. I’ve just started freelancing after the birth of my first child - both of which I thought I’d never do. But loving the freedom I have and feel if I can conquer the fear of motherhood and freelancing all in one, then anything is possible!

  6. Very inspiring Robert. Glad you have found your niche - looking forward to more articles from you.

  7. Great post. Love FS. Thank you for all of the resources and inspiration you give us!

  8. Certainly inspiring. I love the fact that there are many other freelancers out there with weird hours.

    It is also important for everyone to realize that you should not be ashamed of having a normal job when trying to get your business off the ground - this is normal! When I first got Insidedesign going, I was taking anything I could get my hands on!

    Thanks for the post :)

  9. Very inspiring! Great quote, “Put fear aside and just do it. Otherwise, nothing is going to happen.” You just helped my make a very hard decision today. Thank you!

  10. Hard work is no longer enough. you need guts too…

  11. Thank you for sharing your experience. You are right about being out there. It does really take one to approach first then having to wait around for someone to take notice. I wish you continue success!

  12. Great history and thank you for the encoragement.

  13. When I am successful in two years I will start my own blog and give back like you have done. Thanks for the inspiration!

  14. I have been contemplating leaving the 9-5 for some time now. Articles like yours give me the extra boost I need. Thanks for sharing your experiences!

  15. Congrats! I quit my “real” job a year ago too, so we celebrated that last night coincidentally.

  16. Great post. It’s been 2.5 years for me as a medical writer/editor, and I’m only just now getting around to thinking about blogging. Funny all the different paths there are to success!

  17. Wow.. great article, really inspiring.. I think I want to print this and read it out loud every morning. And maybe one day, I’ll read it out loud to my current employer.

  18. Specialize matters. You need to focus into a specific skill and being able to collab with team and the rest will be fine.

  19. Hi
    I have been looking into freelancing for quit sometime now. But there still is a fear of getting into the field. I love writing and have written short stories. I need some expert advise from you.

    Aparna

  20. Very inspiring, although my freelancing career has been much different. I opened up shop in 2002, selling imported electronics evenings after my daytime job. Almost three years ago, I quit my underpaid job and picked up a fulltime project as an engineer as a freelance consultant. I have been working on fulltime projects ever since.

    Today my freelance career has brought me a beautiful family with two kids, a nice house and enough dough to live a quality life. Currently things progressing in a way where I am looking to ditch the fulltime work and pick up smaller projects to make time for my webbased activities.

    Freelancing, being independent or whatever you prefer to call it, it is the only way for me!
    Keep it up, everyone. You can make it, as long as you believe in it!

  21. It’s a fun ride isn’t it Robert? I remember when you interviewed me like it was yesterday. I’m coming up on five years solo now and it’s gone by in a flash. Keep up the good writing!

    –rO

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