One of my most entertaining stories that I like to share about a friend of mine is the time this friend attempted to have 2 jobs in 2 different cities at the same time.

This particular friend had attempted to keep a job as an attorney in Washington D.C. at the same time that he had another legal job in New York. The reason he did this was that his New York job was unpaid and he needed the money from the other job, but the unpaid job was a prestigious one that could have led to other opportunities later on. When I asked him at the time how he planned to manage this, he explained that he spent a few days in the office in DC, then said he was working from home for the next few days and then would get on the train to go work in New York. He would go back and forth between the two cities about twice a week. He often had to come up with excuses for the New York job as he was under a more watchful eye there. Needless to say, this didn’t work out too well and he ended up getting let go from both roles after about 4 months but I had to admire the penache of someone who thought they could pull this acrobatic feat off.

Little did I know that this friend was merely ahead of his time. An article in The Wall Street Journal today, showcased workers who were managing secretly working at 2 jobs. They are able to do this by working from home at 2 different companies. The article seemed to have been inspired by the blog of one such worker called overemployed.com who shares tricks and tips for those looking to pull this feat off.

What caught my attention about those workers featured on the article was the number of those that felt justified by their sense of disconnect that they feel to their employers. This disconnect was not born out of working from home but had been building from long before. Many spoke of how they felt aggrieved from being passed over for a promotion or they worried that they would be laid off anyway. Few if any employees are employed for life anymore, it only makes sense that lack of employer loyalty would then be followed by lack of employee loyalty. Getting another job at the same time was a way for them to take back their own power and it’s hard for that not to resonate with anyone that has worked for a large company.

What also struck me about the stories related in the article was the number of people who felt there is just too much unproductive time spent at a single employer. I especially identified with the worker who said he had just come out of school and felt the corporate environment was not what he expected. He explained that his experience made him feel as if many people were filling their calendar and looking busy but not much was being produced. Rather than adapt to that particular approach, which seems more political and fear based, he just decided to get another job and produce more.

This is not unlike the approach I took myself in starting this blog. Frustrated with office politics and seeing the spillover benefits of my investing on the side as well as reading, I decided to devote my energy towards sharing that with an audience with an aim towards educating and provoking conversations rather than just sitting there frustrated.

Short vs Long Term

Yet as tempting as it may be for some, getting a second job isn’t the only way to ramp up earnings and take back control of your life. Work from home is just another step towards a new world where work starts to become more results oriented as opposed to connections oriented. What I mean by that is that now more than ever, people can “take the side” door to prosperity rather than toiling away under the corporate machine and hoping you get promoted into prosperity.

The gig economy is a fantastic way to do this. Getting a side job or a second job is not the only way to supercharge your prosperity. I have been examining a number of ways to do this recently through saving, investing and using credit to get things off the ground. The point of all of these is that whether it is extra money or through reducing your living expenses, all of them act like a snowball over time which, if done right, can start to produce fantastic wealth with little effort given enough time. Lately for me these include:

• Lowering My Housing Expense – After years of keeping my expenses low by living in a studio apartment, I now plan to buy a 2 family home. My mortgage will be offset by renting part of the home. Believe it or not this can end up coming to the same or even lower cost for housing than what I currently pay for a studio and could significantly upgrade my life, essentially quadrupling the space I have to make room for my new step family.
• Buying a Car to Rent – I came across this idea the other day via some YouTubers that buy used luxury cars out and then rent them out on sites like Turo. I am not looking to make tons of money here but if I can have another car which then offsets the low cost of my current fully paid off car as well as offering me a few days to drive it during the month I consider this a win. This could essentially reduce my car expenses to zero.
• Refinancing My Rental Properties – I made an investment earlier in the year to upgrade one of my properties which has paid off in it being appraised for 25% more. The long term investment and waiting for price appreciation is paying off here.
• Taking a 401(k) Loan – I wrote a post about this a while ago but realized that saving $500 to $1,000 a month over years didn’t make sense if I was just going to invest the money. In this case it makes more sense to borrow from my future savings and put that money in the market now. My 401(k) savings are ahead of schedule so I can afford to shift some savings to the taxable pocket.
• Investing in Myself – I missed a few weeks of posting to take the CFA level III exam which I didn’t pass. This wasn’t about having letters after my name but was more about re-taking up of a challenge on something I didn’t finish. Even if I didn’t pass there were spillover benefits to the knowledge I gained such as switching my retirement contributions to all Roth 401(k) contributions from pre-tax ones. I have signed up to take the exam again in November.
• Improving My Health – Spending quality time with family, exercising and working towards mental balance have been hallmarks of the time spent working from home. I would have likely spent my morning commuting or reading while eating lunch. I now spend it running 5 miles a day and doing calisthenics which has me in some of the best shape of my life. I get to spend more time with my son and step kids as well which is invaluable time I won’t have again.

I started my journey investing seriously 13 years ago when I left graduate school and spent many years investing simply and toiling away long hours at work while many others at that age partied and blew their money. For the first time now I feel I am starting to see the results of those habits. Doing a brief calculation, I was able to deduct that the results of buying a cheap apartment and then buying a rental property 11 and 8 years ago respectively, has made me the equivalent of having earned $70,000 more per year over the last 8 years and that doesn’t include my retirement investments. Just as important as earning more is what you do with the money you make. All this was despite many pitfalls including a failed business venture and going through a divorce.

Sharing vs Gig

The gig economy is often lamented but it has provided opportunities to earn income outside of a regular 9-5. It has allowed those who would like to earn extra income in their spare time the opportunity to do so without having the long term commitment of a regular job. I can remember a time when the only way to make extra income was to try and pick up more hours at work. The gig economy has channeled those extra hours worker want to where they are desired most.

Combining this with monetizing assets such as cars, tools or any other physical goods that can be leased via the sharing economy has unlocked idle assets and lowered the cost of ownership. These are not as easily quantified via GDP figures but have surely increased the living standards of those that utilize them. Combine this all with low interest rates and it’s now easier than ever to make extra income, purchase assets with little capital and then monetize those assets.

It’s no coincidence that early retirement and full time freelancing are becoming ever more popular, especially with younger workers. The fact that some are able to hold down 2 jobs while home, even if it’s in secret speaks to the inefficiency of office politics and time wasted looking busy. Apart from the workers themselves, shareholders of these same public companies should start putting pressure on executives like James Gorman of Morgan Stanley to embrace work from home and the potential lower costs that it could bring, increasing that sacred bottom line. It seems freelancing for skilled white collar workers, similar to what software engineers now experience from their employers, is on the horizon for other workers in the near future as well, no matter what the old guard thinks.

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