So. I’ve never actually written a year-in-review type post before. At least, not that I can find. The closest I can come is this post from the beginning of 2018. It’s not a year-in-review so much as a forward-looking post at 2018 in front of me. As that post says, I’m not much for New Years’ Resolutions. Though I am all about reflection, so this revelation is actually a bit surprising to me.

Or, maybe because I’m so contemplative on a regular basis it’s never really seemed worth the effort to write an end-of-year summary. That streak ends today, as I look back on 2019 (and a bit at 2018). There’s no doubt the last year or two have been some of the most interesting and challenging of my life.

2018: A Quick Look

The year started off normal enough; school, work, politics. I had no idea what was in front of me.

Taking a night dive into uncharted waters, in March of that year, I left my job in the Governor’s Office to take a position as the Campaign Manager for Kim Coco Iwamoto in her bid to be Hawaii’s next Lieutenant Governor. I left the stability and safety of a dead-end job for an exciting new one which I didn’t know where it would lead. Or what would come next.

Finishing a disappointing fourth place, it was nonetheless a tremendous experience I’m glad I had. Not understanding how hard things would get financially, I took the remainder of the year to try to stand up my own consulting business and finish my Master’s Degree at GW.

2019 Began with Hope and Energy

2019 saw me graduate from George Washington University, my first official consulting client, and travel for work.

By the time January came around, my bank account had dwindled to pennies and my credit card debt had exploded. But I was hopeful because I also was making better-than-decent money consulting.

I was doing the work I loved on causes I genuinely cared about. Things were great. My business was taking off and I thought I was on my way.

But then the dumpster fired of a legislative session came to an end. And so did my contracts. At the time, in early June, I was still somewhat hopeful that it would only be a matter of time before the next gig came around.

Then, Reality Kicked Me in the Head

Again my bank balances dwindled, credit balances continued to rise and I didn’t actually find any other work until the end of October.

Being self-employed can be great. Freeing. Fulfilling. For me, there’s not much better than sitting down at my desk with freshly made coffee still in sleep attire. No shoes or pants required.

It can also be incredibly difficult and lonely. I went from working in an office full of other people to spending more than a few days working from home. It’s not an exaggeration that I am not social. Even in the office, I’d rarely talk story with my co-workers. Except when I did.

Having the choice was something I didn’t think I’d miss. But now I can easily spend a few days not leaving home except to venture out for meals or smokes. Being alone with my thoughts can take a depressing turn at any moment. Staying focused can be challenging.

I started to think maybe I had made a terrible mistake risking stability and comfort to venture out on my own. I applied and interviewed for a few full-time jobs back with the State, though none went anywhere. Had it not been for the love and support of my parents, it’s likely I would have been forced to pack up and move back as a failure to my high school bedroom to start anew.

I’m an Odd Mix of Hope and Brutal Reality

My life in Hawaii hasn’t been without challenges. From long bouts of unemployment to a chronic illness diagnosis and major surgery, my 17-plus years in the special place has molded who I am as an adult. Despite these challenges, I’ve always managed to land on my feet. Sooner or later.

So, while I continued to struggle toward the end of 2019 I started to think, again, about packing it in. Then, I received a call for a job that sent me to Mississippi for two weeks of work. It couldn’t have come at a better time. It was a great experience I’d happily take up again. And it kept me solvent for another month or two.

Strangely, when it comes to my personal life, I have long since given up on the possibility of “meeting someone”. Instead, I’ve chosen to focus on other parts of my life. Professionally though, I’ve always managed to stay mostly positive. Despite struggles and financial ruin (at least twice now), I continue to hold out hope that it’ll work out in the end and that I’ll be successful. Eventually.

Looking Toward a New Start in 2020

While I contemplate how best to deal with the crippling debt I’ve acquired over the last few years, new professional opportunities present themselves.

The 2020 Legislative Session begins in just a few weeks. And it won’t be long before the election season kicks into high gear. It will no doubt be a busy, stressful, and challenging year. As I sit here with my morning coffee on January 2nd, I am hopeful. Hopeful that income will begin pouring in. Hopeful that at least some of the projects on which I’m working will be successful. Hopeful that 2020 will see my business grow.

Here’s hoping. And here’s hoping 2020 will be a positive year for all of you.

Time to get to it.