Boost Your Organic Motivation

My biggest weakness is being unable to generate enough organic motivation to keep on hustling. I used to get up by 5am every weekday to work for 2-3 hours before work. Then I’d get home by 8pm and work another 1-2 hours on my side hustles. There was this massive internal drive to go all out to one day break free.

Now that I don’t have a day job, I get up around 6am and then zone out on my phone for 30 minutes before checking the refrigerator several times to see if there’s anything good to eat!

No wonder why my weight continues to creep higher. I’m just not trying hard enough. I admit it. Reaching financial independence has made me less productive by at least two hours a day. What a shame to no longer reach maximum potential.

Then one day I realized I had been sitting on two, $2,100 rent checks from my Pacific Heights tenants for one week. They’ve been great so far in terms of paying promptly. The only reason why I remembered carrying these checks is because I told my tenants to just take the cost of fixing the leaky kitchen faucet off their rent.

They reminded me they had already sent their rent checks, and given rent wouldn’t be due for another 3.5 weeks, they’d rather just get reimbursed directly. Oh yeah, that’s right.

The main reason why I forgot to deposit the $4,200 for a week is because I paid off the mortgage in 2015. After 13 years, the bank is no longer helping me stay financially disciplined.

Quarter Life Crisis

There’s so much history with this Pacific Heights rental property because I bought it when I just turned 26 in 2003. At the time, I was also losing my organic motivation after saving up around $200,000 and making $150,000 in a fortuitous internet stock four years after college. I knew I was lucky, but I was also tired of working 70+ hours a week.

Waianae Mountain Range

9/11 was fresh on my mind and I was constantly wondering what was the point of working so long to make more money. I was incredibly tempted to just leave San Francisco and move to this beautiful 6.2-acre property my grandparents owned nestled in the Waianae mountain range in Oahu. Due to their advanced ages, they were no longer actively tending to the dozens of mango trees, pomelo trees, avocado trees, and orange trees they had planted decades ago. What a shame to see their hard work fade.

As I contemplate this quarter life crisis now as a middle-aged person, I realize how dangerous it is to grow up in a household with some wealth. As grade school teachers, my grandparents weren’t rich by any means. But they did buy this amazing property for $50,000 in the 1960s. If there wasn’t this property, I wouldn’t have even considered leaving work in my mid-20s due to a lack of options.

Taking on a $464,000 mortgage at 26 super charged my organic motivation. I changed from wanting to kick back in Hawaii to wanting to get into the office by 6am and outwork everybody every day. The last thing I wanted was to get laid off with such a large amount of debt. Debt saved me from short-circuiting my career by eight years.

If I moved to Hawaii at 26, I might be an incredible surfer by now. But I would have always wondered how far I could have gone in my career had I stayed. Now I have no regrets because I tried my best to get to Managing Director and failed.