2019 brought some radical changes for me. I quit my job in May with the intention of taking a sabbatical, spending more time with family, and thinking about what I might want to do next and where I’d want to be. That entailed saying goodbye to a lot of friends in California and a work/social life I was pretty comfortable with, putting my things in storage, and driving cross-country back to NY. (I talk about it in my video blog update.)

I’ve had some amazing family time in the last six months and great visits to friends I hadn’t seen in ages, so that part of the sabbatical has been a success. However, I haven’t gotten very far in planning my future steps. I’ve found it difficult to focus and yet also difficult to turn off my “getting things done” checklist mentality, despite being unemployed. That results in me filling my time with tasks, then castigating myself for not getting more relevant work done. Maybe some of you can empathize with that feeling, it’s tough because you’re working hard all the time but never feel like you’re making progress.

For me, my best visionary thinking is usually done on the road. When I’m away from home, I can get into a different mindset and achieve more clarity. Some of my best journaling has been done on planes, in coffee houses or in different countries. I have some travel coming up that I hope will allow me some down time and perspective.


Dividends (Primary Income)

I’ve been tracking my dividend income regularly here so everyone can keep up with how things are going. The short version is, pretty well so far. I hit a big milestone in December: my bank account is finally back at the same amount as it was when I quit my job in May. In other words, not only have I not lost money in that seven months, I’ve actually gained some back after all the trips I took. I’m pretty stoked about that.

I can hear some of you thinking, “Yeah but you’re living rent-free currently, right, so how hard is that?” To which I respond, Totally fair comment! But I’m only taking in about 60% of a full time minimum wage job right now – give that a try sometime, even just for discretionary spending and gas. I’ve actually done two sabbaticals before this one so I’ve had some practice, one was just a short six-week getaway (most of which was paid for by the sponsor), and the other was three months in the Bay Area, self-funded, when I attended a startup accelerator. For the second one, I rented a furnished room in a 3BR place in Mountain View for about $1300/month – add food, an occasional $2 coffee with free refills, biking and taking the train to minimize transportation costs, and it was still crazy to see how fast my savings was depleting when I had no money coming in. That was one of the experiences that convinced me I needed to have some passive income streams to make longer sabbaticals realistic.

Real Estate (Secondary Income)

I also started writing back in May 2018 about my real estate investment. That’s been a positive experience and a great learning opportunity overall. Though it barely flows any cash right now, as it continues to be paid off (by the tenants), I’ll be able to collect more in the years ahead while hopefully getting some appreciation along the way. 

My first year tenants renewed for a second year through to October 2020. The property management company has been good about keeping the property maintained (lawn mowing, yearly pest control, and 6-month house inspections with photos), I did find they double-billed me for a lease renewal fee which they refunded when I pinged them. Always read the monthly statements, it only takes a minute or two. I contested the house assessment from the tax board, and that was also surprisingly straightforward. The assessed value was too high and details like square footage and number of bedrooms were incorrect. All I had to do was use an online tool at the county website to describe what I was contesting and why, select comps around my property, and submit a number I felt the house was worth for tax purposes. The county appraiser then contacted me by email to ask if I still had the purchase appraisal sketch, which I sent him, and they accepted my number. 

Thinking bigger for 2020

I’m finding that decades of working a 9-5 job, and maybe just societal pressure in general, have narrowed my mindset. I have a hard time thinking about vacations longer than two weeks. I keep feeling unsettled and homeless, despite having a comfortable place to stay here in NY and friends around the country that would love to host me (for short visits). I feel a lot of pressure to decide where I’d want to live long-term and find new investment opportunities, despite the fact that I’m very blessed and could probably survive as-is perpetually. (Not that I want to, but it’s grounding to remember I don’t have to work.)

I aspire to be someone who takes risks to follow what I believe is right for me, and not what others might think is the normal path. I fail pretty often. This year was a big, risky step away from a successful corporate career and towards the break I’d wanted to take for years. My goal for 2020 is to try and broaden my thinking and really maximize – not optimize, but maximize – the opportunities that this sabbatical gives me.

Happy 2020 everyone! The start to a new decade.

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