Filling The Void In Early Retirement With Part-Time Work

Hawaiian Sunset With Sailboat In Retirement

Over the past one and a half years since leaving Corporate America I’ve done some deep thinking about early retirement through posts such as:

* How Does It Feel To Retire Early?

* Should I Go Back To Work Now That The Good Times Are Back?

* Do You Work Harder Or Relax More During Good Times?

* The Startup Riches Myth: Sell For Millions And Still Not Be A Millionaire

When you’re used to working 12 hour days every day for 13 years it’s very hard to suddenly downshift from sixth to first. You’ll blow up your engine if you do. There needs to be a gradual progression whenever large life changes are made.

The first six months of retirement I was second guessing myself on whether I made the right move. I had just turned 35 years old and short-circuited my career in finance so I could spend more time traveling and doing this new thing online. I worked my ass off to finish writing my book on “How To Engineer Your Layoff” so I could at least say that I produced something meaningful if all went to hell.

My doubts began to calm down during my second six months of retirement because I was able to take a 2.5 week long business trip to Europe to research the happiest people in the worldTraveling while writing and maintaing my online business helped crystallize why I decided to leave Corporate America in the first place – more freedom!

The final six months have been an absolute blast, with six weeks this summer in NYC, Mallorca, and Switzerland (links to FOMO, finding perfect summers, and eradicating apathy) and four weeks this winter in Hawaii all the while working of course. There’s absolutely no law against having fun while traveling to understand different cultures to share them with all of you in my writing. The key is moderation.


Do You Work Harder Or Relax More During Good Times?

Man under a personal umbrella relaxingThere’s an old saying that one should, “Make hay when the sun is shining.” When I was in my 20s I had two modes of work ethic: 1) Work hard and 2) Work harder. I’d wake up around 4:30am every morning in NYC from 1999-2001 to read the Wall St. Journal before walking over to 1 New York Plaza for work at 5:30am. I knew knowledge was power and I had neither.

After the 10 year mark, I began to burn out. Perhaps all the traveling, stress to perform, ridiculous market cycles and business school classes while working started taking its toll. I did everything I could to increase financial returns when the times were good because times would eventually turn sour. When times were bad, I felt I needed to work harder so as not to fall too far behind. People were getting fired left and right back in 2001-2003 and 2008-2012.

Ask anybody who has worked on Wall St. since the late 90s and they’ll tell you that 2007 was the last great compensation year. It’s been downhill ever since. There was no longer hay to be made, even if we are reaching new highs in the stock market. I woke up to the realization in 2010 that the outsized returns in finance were over, at least for the foreseeable future. So instead of complaining about working harder and getting paid less each year, I got out in 2012.


Making The Most Of Company Off-Sites: More Productivity, Less Boondoggling!

Hawaiian BeachThe sun now sets at 5pm and it only gets to a high of ~64 degrees nowadays in San Francisco. Despite the cold, winter is one of the best seasons in Northern California thanks to epic powder up in Lake Tahoe three hours away. I’ve got my season pass on hand and I can’t wait to carve it up at Squaw Valley. What’s better than shredding down a 2,800 foot vertical and then grabbing a beer with friends in a hot tub? Nothing!

Before the snow falls there’s this awkward time between November 1 – December 1 where it’s cold, but not cold enough to bring about consistent natural snow. My resort closes down for three weeks in November for maintenance and artificial snow production to build the base as an example. Can you imagine living in a cold climate without anything to do? That’s like living on top of a hill with no view.

As CEO of my business, I’ve decided to make an executive decision to host an annual company offsite in Hawaii every November to December. Going to Hawaii during the winter maximizes one’s appreciation for the islands since the weather ranges from 70 at night up to 82 during the day, everyday without fail. Hawaii is also one of my key retirement hubs I’ve got to do more research on before permanently relocating for an estimated six months a year. The other six months will be spent between San Francisco, Lake Tahoe, and traveling.

After attending a disappointing company offsite in NYC where we were locked up in conference rooms the entire weekend, I promised myself if I was ever the big boss I’d do it right for my people. A company off-site should exist to build relationships, improve profitability, and make work fun. I’d like to share some thoughts on creating a company offsite agenda for maximum business efficacy.


When Is The Right Time To Quit My Job And Do Something New?

Long Term Unemployment Chart

Source: Bureau Of Labor Statistics

A baby panda dies in a bamboo forest every time someone quits their job. One should never quit their job just like one should never make an investment in something they don’t understand. Always get laid off to receive benefits such as free COBRA, WARN Act pay, severance pay, deferred compensation and unemployment insurance. Figuring out how to get laid off instead of quitting bought me literally six years worth of San Francisco-level living expenses to pursue entrepreneurship.

Without such a long runway of financial support I probably would be more stressed in my pursuit of creating a lifestyle business. There’s no way I would have spent $20,000 to take six weeks off this past summer either due to a constant worry my online revenue would fade. I’d feel guilty experiencing so much freedom only a year post Corporate America. Making money while having fun is an odd feeling that takes time getting used to.

For those of you who are too stubborn to take my advice about never quitting I’d like to give you parameters to think about before throwing away what’s likely your largest revenue source. By way of background, I’ve consulted with dozens of individuals who have successfully made a small fortune by leaving their jobs. I’ve also consulted with a handful more individuals who just said “Screw it, I’m quitting!” One of them moved back home with his momma. A couple others gave up and went back to work 10 months later. A couple other quitters are still slogging it out on their own. Don’t be a quitter. Be an engineer. A day job is so much easier than entrepreneurship!


The Startup Riches Myth: Sell Your Company For Multi-Millions And Still Not Be A Millionaire


As I head off on my 12 month journey to build into a online advertisement exchange in the personal finance space, I remind myself about the long shot chance of success. I’ve always wanted to be an entrepreneur since middle school, and finally after 20+ years here’s my chance.

There’s an idyllic notion that once you’ve sold your company for multi-millions of dollars you’re filthy rich and never have to work again. I admittedly have this automatic mindset whenever I meet someone who said they sold their company to one of the tech giants. Even if they are still living in a one bedroom apartment with their wife years after the sale, I just think they are being frugal.

By also believing everybody makes 10X more than the value of their car based on my 1/10th rule for car buying I’m able to keep motivation high to work harder since even a Toyota Corolla driver is clearing $200,000 a year nowadays. The goal is to give into the illusion of wealth in order to eradicate self-entitlement.

There is startup fever here in the San Francisco Bay Area partly because of all the stories we hear about 1,000 bagger returns in companies such as Google, Facebook, Instagram, Twitter, Tumblr, AirBnB and more. Sure beats investing in stodgy dividend stocks doesn’t it? Real estate is on fire and it seems like everybody in their 20s and 30s are tech millionaires. Given we have a culture of stealth wealth in San Francisco where you can’t tell a rich person from a poor graduate student, the possibility is real that your unassuming neighbor is rolling in the benjies.

The fact of the matter is that the vast majority of startup founders never make it past year three and even less sell for multi-millions of dollars. Even if a founder sells her company for $30 million dollars to Apple, she probably could have done better working a day job all those years instead, with much less stress! (Related: Joining A Startup Will Probably Make You Poorer Than Richer)

In this article I’ll share with you a very insightful conversation I had with a man who ended up selling his company for tens of millions of dollars circa 2010 three years after business school (Should I Get An MBA?). You’d think as a 30-something year old, he’d just be kicking back on his own private island somewhere blogging right? Not so at all. But before we go through this fella’s example, let’s go through one of my favorite business assumptions first.


When Is The Best Time To Start A Business? When You Are Young, Broke, And Naive

Young Siberian KittiesSince I was 12 I’ve always wanted to be an entrepreneur. I was surrounded by kids whose parents started beverage companies (e.g. Yeoh’s) or launched wonderful resorts (e.g. Pulau Tenggol) while living in Kuala Lumpur, Malaysia. They lived in nice homes and drove fancy cars. I was smitten. Yet even when I was given a clear opportunity to go to China for a startup opportunity in 1999, I couldn’t say “yes” because I was scared and received an offer from a bulge bracket firm in NYC. Nobody turns down Goldman Sachs right out of college so I toiled in the finance world for the next 13 years.

I’ve always wondered what my life would be like if I took the entrepreneurial path instead. My Mandarin would be excellent, that I know at the very least. Maybe I would have been prescient and bought as much property in Beijing as possible before prices rocketed through the roof. Maybe I would be thrice divorced with multiple children given the rules of business engagement are quite different out East. Who knows, but it’s always fun to pontificate.

By the age of 35 I decided I had enough of working for someone. Although I was scared of leaving the comforts of a handsome income, I also knew I’d regret not finally giving entrepreneurship a go in my 30s. Unlike being a nubile 22 year old, I was an industry veteran in finance with an MBA and a large financial safety net thanks to all those years of savings. What was there to lose except for everything?

Major props goes to those who start businesses after becoming a parent. If I ever become a father I think I’d be so focused on not messing parenthood up that I’d leave little-to-no time for entrepreneurship. As a result, my chances of making it as an entrepreneur would be slim-to-none. I’m a very focused individual who is unwilling to fail due to a lack of effort.

As soon as I left Corporate America, I began writing twice as much on Financial Samurai. I created a brandable product on how to negotiate a severance package within the first four months of being free. Coincidence or not, as soon as the book launched traffic more than doubled every month since. Although income from the book is still only a measly $1,000-$1,500 a month on average, total online income streams grew to the point where it’s now greater than my current passive income streams. I think I’m dreaming most of the time.