Well that was unexpected. Earlier this month I got an email, then a phone call, and then visited a company that likes my writing. (Echoes of Sally Field’s “They like me. They really like me.” come to mind.) Serendipity happens. The conversation happened as my brain has been considering too many scenarios – that have suddenly crystalized down to a few, like a super-saturated solution coalescing into something sweet. Yet another new era begins. I now have a job as a writer, and a writer about something I know something about, Whidbey Island.

Barack Obama was elected in 2008. This blog started about that same time because my book about personal finance, Dream. Invest. Live., was published then. Coincidence. Two memorable events in my life – and a recollection of a dance that was happening that night. A very dynamic day. I moved to Whidbey Island in 2005, so I was already was familiar with Whidbey. Since then, dozens, possibly hundreds of posts mentioned the island, particularly its community of nice people. So, there’s some history there.

Fast forward to 2017. This blog, which is supposed to concentrate on personal finance, was getting crowded for topics. That, and my decision to become a real estate broker, meant I should have a blog dedicated to Whidbey. Not a surprise; a broker has a lot to say about the area where they work. AboutWhidbey.com was launched. 

Skip ahead to the Spring of 2023 and I was no longer a broker and accepted a job at a non-profit that works to benefit the entire county, Island County. I was a Project Manager at the Economic Development Council for Island County. (Tom Got A Job) It sounds like a government job, but it is independent. Nice. It is also for all of Island County, which suggested that I remove bias from my public activities, so I gave up my Whidbey Island blogs (AboutWhidbey.com, WritingOnWhidbeyIsland.com) because they had the word ‘Whidbey’. 

That’s all normal and positive and progressive. But lately, people familiar with my writing mentioned to me that they noticed I wasn’t writing as much. What happened? I’m flattered and surprised that anyone noticed, but evidently, people do and did. Flattered and surprised.

And then came the call. Would I write about Whidbey Island for someone else? And get paid?! Uh, yeah.

But I have this job, you see…

But I have also not been able to work enough on my book (the sequel to Firewatcher), there’s a screenplay that I’ve been highly and repeatedly encouraged to write, several other projects like teaching classes (self-publishing, social media) and public speaking (see Events), a game about Whidbey, some inventions, and selling my books and my photos. I can’t fit that all in, even without a full-time job.

So, do I have faith in my abilities? With all of that going on surely something can generate more than enough income. That is more likely to happen if I work more on those ‘irons in the fire‘.

But, a full-time job with benefits. Stability. Respectability. Conventionality.

But, shouldn’t I be able to make more from what I’ve made? So far, no; but there are hints of hope.

This dilemma has been nudging me for weeks. I even considered selling my house, moving away from Whidbey Island, and buying a small house somewhere more affordable so I could be debt-free. I’d have to live off Social Security and a small pension, but debt-free is a nice place to be, so I’ve heard.

Ah, but a part-time job bridges full-time stability and solely entrepreneurial.

I’m not going to list all of my reasons and all of the scenarios because that can get dull, especially because I can be good at assessing lots of details and their interactions. Key for me, but boring to anyone else.

You may have noticed that I haven’t mentioned the other company. I’ll do that after papers are signed. Between the two jobs is a leap of faith and trust. 

There’s that leap away from stability and convention. I’m leaving a full-time job with benefits to return to gig work and its uncertainties, but relying on projets that may take months or years to complete. Of course, modern life is overflowing with uncertainties. AI, aliens, climate crisis, an un-uniting of the United States, the self-inflicted implosion of Russia, financial crises, and fill-in-the-blank with whatever is in today’s news. There is no escaping uncertainties – except maybe for an off-the-grid cabin in North Central Washington where the uncertainties are switched for uncertainties about power, water, sanitation, food, et al.

I’ll pass along the details about the new job as web sites, email addresses, and such come in. Besides, that’s one more opportunity to mention the work.

I chronicle this because this blog is about personal finances. Because of federal regulations it is safest for me to use me as an example. I am only one example, but each example has lessons. The work world has changed since I graduated college in 1980. I’ve been fortunate enough to witness the rise of the keyboard, which was also the diminishing of the secretary; the entry of electronic networks (at 300 baud), which meant fewer trips to deliver data; the introduction of the Internet, which became ubiquitous but which also shifted paradigms; the rise of the Gig Economy, and the resurgence of unions; the ability to work from anywhere, and the value of remaining socially connected IRL (and the use of texts, hashtags and TLAs); and the very welcome increase in diversity and awareness and trust in everyone in the workplace, ideally.

That long history also reveals a aspect of my life. I am getting older. Duh. Advice that made sense for a twenty-year old (get out of debt even if it takes years before launching your life), assumes a value of time; but that value that shifts with age. I’m over 60. Hopefully, I have many healthy years, still; but my 65th year will feel more precious than my 25th year. There’s less time to fit everything in between 65 and whenever. There’s also an appreciation of the value of things I was ignorant about forty years ago. Sunsets, conversations, dances, quiet times, times to celebrate have more feeling now, than then. 

I guess I’m part of some new shift. This is a major leap for me, but a small step for the economy and its workers who are similarly redefining work. And I am convinced that because of AI and the rest (even aliens?!) the economy is about to see its own major leap. 

Stay tuned because this story isn’t over.