Road through Rio Puerco. Photo by Peri Pakroo.
I like the untraveled roads. Photo by Peri Pakroo.

As a long-time self-employed person I’m always (srsly always) on the lookout for new opportunities and strategizing about how to keep my career evolving in a way that keeps me happy. Having been at this a couple decades, I have over time developed a pretty good working formula for happiness which is (roughly):

  • doing challenging work on topics that interest me
  • contributing to my community(ies)
  • having enough quality time with family and friends
  • being regularly creative, especially with music, and
  • earning enough income to minimize life stress and allow for down time and travel.

That’s pretty much my formula. At any given moment the mix can be heavy in some elements and lighter in others. It’s constantly in flux.

But there is one constant, and it’s a big one: It’s all up to me to figure it out. All of it. Which is a lot.

Depending on the day, being my own boss can be exhilarating, or it can be exhausting. Most self-employed folks say the same thing. Some days, it’d be great to have a boss to just make the important decisions and set the agenda. Some days you just don’t want to think, to decide, to Be In Charge.

I never find myself indulging these feelings for long, probably because I’m simply in love with the freedom of self-direction. I’m also at a mid-point in my career where a lot of the early hustle has borne fruit and I’m not as uncertain (or sometimes panicked) that I’ll never get another paying client. That’s not to say it’s all easy street these days, but there is definitely more predictability (and less stress) now that I’m a couple decades into an independent career.

I’ve been thinking about these things lately because I’ve found myself wanting new challenges with my professional work, and spending a good amount of time thinking about and teasing apart what it is that I really want. What kind of projects make me happy? What new element(s) could I add to the mix of stuff that I do that would feed me personally and professionally?

I ask myself the same questions that I ask many of my coaching clients:

  • What’s the next best move for me?
  • What are my longer-term goals, and what steps can I take today to make them a reality?

For anyone that follows my personal Facebook or Twitter feeds, it won’t surprise you that I’m rather obsessed with political issues. This is nothing new; I double majored in International Relations and Philosophy in college. I’ve always been a bit of a news junkie — then 2016 happened, and my interest in politics and law became more than a passing concern. The things I learned about the Constitution in law school were suddenly not just abstract concepts but the subject of active legal warfare. I have been following and posting about the assault upon rule of law in our country, and my love of politics and law has been completely reinvigorated.

In addition, my desire to contribute something positive to the world has been mightily stirred. The direction our country and the world are going frightens me, and damn but I have to do something about it.

So, how to work this into my professional life? Here’s how I’m approaching it. I am not a trained journalist, nor do I have the academic background to do “think tank” work. What I do have to offer is deep knowledge about and experience with small businesses, entrepreneurship, nonprofits, publishing and communications, as well as ninja-level skills with bureaucracies and legal processes.

So step one was clarifying some of those basics in my own mind. I spend time doing this on the regular, but last summer I put more sustained thought into what I want to do, and what I have to offer.

After a few weeks of musing, reading, and making lots of lists and notes, I realized that I loved the idea of putting more of my efforts towards supporting the immigrant community, both with advising people about self-employment, as well as assisting with legal needs. I started reaching out to local nonprofits (starting with my personal network) and have gotten connected with some great folks. So far I have volunteered a bit with processing asylum paperwork and am getting involved with some small business support efforts.

With this refinement in my career direction, I was also reminded how much I have wished I were at least semi-fluent in Spanish. So last fall I reached out to find a tutor who would meet with me weekly and help me tiptoe towards language proficiency. I simply don’t have time for a real class right now, but doing the weekly lessons is really helping me get a decent foundation.

My dream outcome is to become fluent in Spanish and pursue work abroad for at least a year or two. That’s my long(ish)-range goal. By habitually revisiting that goal and continually steering my short-term activities in that direction, I feel good about where I’m at.

I thought I’d share my “blue sky” vision with you today because I’m a believer in this kind of planning — and I am a classic example of how a self-employed person does not typically follow a neat career path. It’s easy as an independent worker to doubt our goals or plans for seeming crazy, or weird, or impractical. But as your own boss, the beauty is that you get to choose your direction. That’s why we are self-employed, right?

The trick for me is to make it a regular habit to check in with my longer-term goals, and to tie those goals to my shorter-term to-do lists.

How do you chart your course? I’d love to know!

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