My thoughts on Freelancing

I never wanted to be an entrepreneur. Too risky. Too solitary. Too much work for too little reward.  Moreover,  I was never SO passionate about what I was doing that I wanted to work on it all.the.time. which is how I saw most entrepreneurs I knew.   When I was a senior in college, I took a class on entrepreneurship.  It fulfilled an elective requirement I needed, and met at a convenient time.  It was a masters class, with a fun group of students, a good professor, etc.  Most of the students in that class were there to work on their (already-hatched) business ideas, but the main thing I learned was, “Never in my life do I want to be an entrepreneur.”  I went on to work for a large engineering firm, and then to graduate school – all with the aim of returning to the corporate world.

Did I ever mention that moving abroad takes all those life plans and tosses them out the window? When we decided to take the opportunity in Ireland, our understanding of Brad’s work permit was that it came with permission for me (his spouse) to work as well.  Although that is technically true, I must have a work permit in order to work. To get a work permit, you must first get a job, and the vast majority of employers I spoke with only wanted applicants that had existing work permits, since the process takes about 12 weeks to obtain a new one.  It was a Catch-22. I couldn’t get a job because I didn’t have a work permit, but the only way to get a permit was to get a job. When I finally obtained the all-important work permit, I ran into further problems.  Most employers, when they saw “USA” on my application, assumed that I did not have permission to work, because I am not an EEA (European Economic Area) citizen. Never mind that I had the all-important permit, they couldn’t get past one line on the application! I have continued to apply for jobs with some success, but have not yet found the right opportunity. (As an aside, this experience of trying to get a job overseas has given me a completely new perspective on immigration issues.)

In an effort to not go stir-crazy with 3 kids under foot (hence the picture above, with the dollhouse for added effect), I started teaching myself how to design websites in WordPress. At first, it was just to tweak items on my personal site.  Then I did a project for a local PR firm, and then another friend asked for help on her business’ site, and now I am working on several sites.  Despite the frustration of looking for full time jobs, my freelance web design business has been growing – with very little advertising or effort on my part.  Just word of mouth. As happy as I should be with this development, it makes me uneasy.  Why is that? I guess I feel this way because I never considered going into business for myself at all, and certainly not in web design. I look at friends and former classmates, and I’m wistful for their careers. I see the life that I willingly stepped away from, for the chance to move overseas. Career path! Responsibility! Salary! Entrepreneurship is never where I expected to be, and sometimes feels like a waste of my skills.  I struggle to decide – should I pour my energy into my freelance business, even though there are plenty of competitors out there?  Should I expand my skill set with more coding skills, even though those tasks can easily be outsourced? I worry I don’t have enough passion, or insanity, to make this gig work.  All the entrepreneurs I know are 150% invested in their work.  What if I’m not?  Is enjoying what I am doing, serving my clients well, and being happy with myself, is that enough?  Or do I need to have the desire of world-domination? (Ok, probably not that.)

On the other hand, should I focus solely on my full time job search, and hope that someone will be able to look past my nationality, and see the value I could bring to their organization? If I were to decide to return to the full time workforce after a few years of freelancing, would employers discount my experience? I worry it could be viewed as “well that’s nice, but it’s not a real job”, but maybe I just don’t have enough faith in myself to sell it as a valuable experience – which it is!  All of this leaves me with a conflicted relationship with freelancing. I worry that it is a waste of time because it doesn’t look like the career I always imagined. And yet, I really enjoy it because it challenges me in new and different ways.

For those of you who are entrepreneurs – are you comfortable in your decision? For those of you thinking about freelancing, what has held you back from jumping in?

8 thoughts on “My thoughts on Freelancing”

  1. Rheagan, I have, if not a similar, then at least an analogous work timeline. All of my energy in college and grad school was focused on the prize of someday standing at the front of the classroom as the professor. And then I married the military, the medical military nonetheless. The logistical nightmare involved in getting a PhD when you are facing moving every 2-3 years to god-knows-where was like a bucket of ice water on all of my goals. So plan B: thriving career in non-profits. HA! Try climbing ANY kind of ladder when your employment at a location has an expiration date. It became abundantly clear that if I wanted a career, it was going to have to travel with me, and that is how I got into freelance grant writing. There was a great deal of adjustment to working from home – no one has any idea how much of one’s social need is filled in an office until yours is a quiet house all day, and lots of other issues of pride and “what a career is supposed to look like” – but it gave me a flexibility and control that nothing else would. With all that said, the grant-writing world (especially after the collapse in 2008) is brutal and after about 8 or 9 years of it I found myself pretty burnt out. However, it had served to open my eyes to how much I really love writing, which then gave me the bravery to step off the cliff and start writing fiction and start our blog. I don’t know if you find any help or answers in this, but I would say that if you are satisfied at this moment with the web design, let it be. It may not ultimately be what you want to do with a capital “D”, but you never know what doors it might open.

  2. I sort of fell into freelancing a year after I had Jack. I expected to get a “proper” job between having 2 kids, but I’ve found that the balance I can strike between home/work has worked well and in the end I didn’t like the idea of having to dial up on my career only to dial it back down again after the 2nd comes along. It remains to be seen whether my gamble will pay off. Maybe a full-time job that I have an interest in will be much harder to come by when I do decide to pursue one. The idea of never being able to get my career off the ground again is pretty sobering, but I’m willing to take the risk. Unlike you, I haven’t invested much in my education and I’ve always sort of fallen into jobs that lead me to places I didn’t know about but am glad I’ve visited. I’m sure if I’d trained more rigorously I would feel more of a duty to myself to realize that investment. I do strongly believe that doing ANY paid work is a big part of keeping your options open. I took a whole year off after having Jack and was really struck by how under-confident I was when I started back – even on the most basic stuff, promising, delivering, working through problems. I am like you though, ultimately I crave the social contact and structure of a “proper” job and I look forward to the day when I can commiserate about some project that got screwed up with a bunch of people at Happy Hour.

  3. “Is enjoying what I am doing, serving my clients well, and being happy with myself, is that enough?”

    The moment I read this, I yelled “YES!!” That is the dream!!” (in my head…because I’m sitting in an office). But then I kept reading, and all of your other questions resonated with me too. I don’t have an answer, but just wanted you to know that all those questions feel relevant to me too, even though I’m not in your same situation. It’s never easy – but I’m glad that you are at least enjoying parts of the journey!

  4. HI ladies! Thank you for all your kind words. It’s nice to know that others struggle with these choices as well. I think the larger societal issue here is that, as much as they are discussed, “on-ramps” for people who have taken time out of the structured workforce don’t really exist. Whether it be to start a family, take an overseas assignment, care for an aging parent, or other issue, there are plenty of reasons that people do not have continuous career paths these days. I think my main worries about freelancing stem from this issue. What happens when I decide to return to the formal workforce? Will my experience be valued? Who knows. The uncertainty is the worst part. On the positive side, I really enjoy challenging myself in new ways, and this web development gig is certainly doing that!

    Is anyone on Github? My next challenge…

  5. Sarah – your blog is lovely!

    I love this: “It may not ultimately be what you want to do with a capital “D”, bu you never know what doors it might open.” Thanks for the encouragement!

  6. I tell people that I “fell out” of the workforce, rather than intentionally “stepped out”. Maybe I fell into freelancing too! When is baby #2 due? 🙂

  7. So glad the post resonated with you as well. You comment about “That is the dream” has me thinking. Perhaps it is my dream that needs to change, rather than my job…

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