Only The Curious

To be self-employed or to be an employee, that is the question. It’s a subject that I wrestle with frequently, because I understand the pros and cons of each, and have been on both sides multiple times over the last 5 years. If you look at my resume, you’ll see that I usually have an office job from October through May, and then am freelancing, doing massage, or maybe working part-time in a gourmet kitchen store over the summer. It hasn’t been intentional; several of those lapses were due to layoffs. But it is interesting. The one year that I had a job during the month of May, it took me weeks to figure out why I was so antsy. Then I realized “oh, this is the time of year where I’m usually sitting by the lake with books like “Making a Living Without a Job””

To be honest, my heart lies in the self-employment camp. Unfortunately, my need to pay for things like my car and my health insurance (funny thing happens when you don’t regularly hold an office job: you don’t get benefits. More on that later…) frequently land me back in an office job.

I could write out a list of all the reasons I prefer self-employment, but Everett Bogue did a pretty darn good job of that earlier this week in his post: “27 Reasons You Should Never Have a Job.” I LOVED IT.

The only thing I would add is this: when I tell people I’m self-employed, they’ll often say “oh I could never do that. I need more security. Isn’t it scary not knowing how much you’re going to make every month?” Um, sometimes. Yeah, there are dry months. But you know what scares me more? Knowing I’m only going to make X amount every month. When you’re self-employed, there is endless potential for growth. I don’t have to wait for incremental raises; my salary could double (or more) in a year because one of my income streams takes off. If there’s a trip I really want to go on or something I really want to buy, I just push for a few more clients. Voila, extra money.

Yes, being self-employed is volatile. You need to save more for the down times and it’s important to have supportive friends, family, and/or significant others. But for me, ultimately, the freedom, flexibility, creativity, and potential are overwhelmingly worth it.

That is not to say, however, that I think everyone should be self-employed. It’s not for the risk-averse, or those who need stability. As Matt Cheuvront said today, Don’t Discount the Value of a 9-to-5.

I will admit that, being self-employed, I’ve spent months being broke while trying to build one income stream or another. It’s stressful. It can be lonely. The thing I miss most about having an office job is the social aspect – having co-workers to grab lunch or hit happy hour with. Not to mention brainstorming. And yeah, the stability is nice.

There are reasons for both ways of working. What I think is most important, though, is the mindset you take to your work. You can’t go into business for yourself thinking like an employee, and yet the most successful employees are the ones who go to work thinking like an entrepreneur. More on that tomorrow.

Tweet This Post

About four years ago I was looking for work and came across a posting for tour guides for Trek Travel. Trek, the cycling company, leads luxury vacation bicycle tours all over the world. Biking, traveling, guiding, planning events… I had found my dream job.

Except the application window had closed a week earlier.

Reading that job posting was kind of like love at first sight. I never forgot about trek, and  11 months later, I applied. I probably spent more time on that application than I had for any of my college apps. They responded, I had a brief phone interview, and they said they’d keep in touch.

But they didn’t end up hiring any guides that year. Or the next two.

Then about a two years ago I got a freelance writing assignment from Wisconsin Woman Magazine for their April issue on  “Travel Tips from the Local Experts,” so I called up Trek Travel and asked if I could interview their president, Tania Worgull. (Trek Travel happens to be based in Madison, WI, where I was living at the time.) I did so, and met with their hiring director in the process. It was great to make that connection, and I’ve kept in touch with them ever since.

Then this fall I moved to Colorado. In September, I found a great job with the Mizel Arts and Culture Center, working in their box office as the Administrative Coordinator. Despite being another office job and another nonprofit job, I’ve really enjoyed working there. My co-workers are a lot of fun, genuinely some of the best friends I’ve made here. It’s been great to be back in the arts world, and I love working our special events.  I was overjoyed to find such a good fit job for me so quickly, and have continued to be excited about what a great fit it is.  I set a goal to stay at my job for a minimum of a year, because I’ve never done that, and I think that kind of longevity will be important at some point. I got insurance in January and it was so satisfying, knowing I had benefits, a stable job, and was settling in to Denver quite nicely.

Then about three weeks ago I saw that Trek was hiring for “Soigneurs;” licensed Massage Therapists to accompany their guests on a two-week long ride across Texas to provide first aid and massage services. It was like the perfect fit glove for my other hand. I dropped Garth (the hiring director) a line, and he strongly encouraged me to apply. He said that if they were able to hire me, it might be a good opportunity to see how I would do as a guide. I had a phone interview two weeks ago, and didn’t think it had gone very well…

But I got the job!!!

I’m THRILLED, but taking it has been a challenging decision. This position is only for 2 1/2 weeks. It’s a one-time gig, with no guarantee of future work. So, I asked my current job for an unpaid leave of absence, in hopes that they would be willing to compromise. But they said no. Flat out. No conversation. They gave me a week to make my final decision.

There was never really any question in my mind regarding whether I’d take this job, even if it meant quitting my current one. But now that it’s come down to that, the reality of that choice is significant. Over the past weeks, I  asked many of my friends for advice and help, not necessarily in making the choice but in coming to terms with what it means (and making sure I’m not making a big crazy mistake.)

It seems nuts to leave a full-time job, one that I genuinely really like, for a two week gig. But then, it’s me, and I’m all about winging it, taking chances, and having adventures while I’m able to do it. I’ve had to weigh a lot of pros and cons, and what it comes down to is that I would really regret missing the Trek opportunity, and I am very confident that I won’t go unemployed for long. I do believe that the bigger the risk the bigger the reward, and that change is always accompanied by growth, and that is always a good thing.

In light of that risk, I’ve given up my apartment as of March 1, so I won’t be tied into a lease without steady income. I’ll be gone for most of March anyway, and have a friend who’s offered her basement to store my stuff for a little while. So once I return from Texas, I’ll be starting over with jobs and apartments… again. It’ll be just like when I first arrived in Colorado six months ago, but with more friends.

In the past two weeks I’ve installed and gotten used to clipless pedals, I’ve been working out like crazy, packing up my stuff yet again, and trying to get all of my ducks in a row to have my bills paid and health insurance lined up. It’s been overwhelming and scary and sometimes I just freak out and say “what am I doing? OH MY GOD. WHAT AM I DOING?” And then I take a deep breath, and remember everything I said in this post, and put faith in the idea that this is a change for good and it will all work out in the end.

It will. And thank you for everyone who has been so encouraging and supportive and reminded me of that. I look forward to sharing more about the ride, about how this choice effects things, and how it all continues to progress in the next few months.

Tweet This Post

I’ve officially been in Colorado for a week. It’s beautiful, and I’ve enjoyed driving around, trying to get a feel for where everything is and what all is here. Yet somehow I thought it would feel more radically different than it does. Really, it just feels like my life,  with fewer commitments and better scenery. As excited as I am to have finally moved, the momentum seems to have slowed. I’m finally here! Now what?

One of my mother’s favorite adages is “wherever you go, you take yourself with you.” The external things changing doesn’t make the internal things change; really, it works the other way around. Problems, habits, ways of thinking and doing things don’t just shift overnight. These are things we have to do deliberately, from the inside out. And usually, no matter where we are or who we’re around, we’ll end up making a lot of the same choices time and time again.

Still, part of the point of moving was to instigate change. To shed the parts of me or my lifestyle that weren’t serving me anymore, and to expand into trying/being/doing new things. So I’m trying to be conscientious about every commitment I make, thinking “is this still how I want to do things? Is there a reason I want to do it this way instead of trying another way? How could it be done another way? What would it feel like if it were?”

I do want things to be exciting and new and different, and yet, I really liked my life in Madison, so a lot of the choices I make may be pretty much the same.  Of course, it’s also rather early in this whole process, and because I’ve been focusing on finding work and trying not to spend money, I haven’t really gotten out and experienced a lot of my new surroundings yet, either. Even the ones I have gotten out to are the ones I know and have seen before, and all the people I’ve been seeing are the ones I already know. In fact, today will be the first day I go out and meet some new folks.

I’m sure this will be like so many things – finding a balance of old and new, exciting and different alongside that which is comforting and reminds me of home. I look forward to exploring it and continuing to share the journey.

Speaking of which, pictures and video from my first week will be up soon. They’re all edited, I just need to get them posted!

Tweet This Post