You Have to Hustle

By Charles Sizemore  |  October 8, 2019

I don’t have many vices. But I admit, I do enjoy a good cigar here and there. It has little to do with the tobacco, and more about the act of smoking itself.

When you light up a cigar, you’re basically stuck where you are for the next 45 minutes. So, you might as well get comfortable and relax. If you’re trying to catch up with an old friend, the smoke and the stench keep the wives and kids away so you can have a little privacy. It’s friendly family repellant, and it works every time.

In fact, I’ll likely have one while I’m in Washington, D.C. It’s a good way to unwind after a long day of presenting and mingling. Maybe while enjoying a tumbler of whiskey. If you’re at this year’s Irrational Economic Summit, I’m sure you’ll see me doing so at some point.

And if you’re unable to make the trip, you can still tune in for all the presentations via our livestream. You may miss out on the late-night cigar chats, but you’ll get the most important aspect of the Irrational Economic Summit, and all from the comfort of your own home.

In any case, last week I met John, an old buddy of mine from college, for a cigar in Fort Worth, Texas. We hadn’t talked about money in years, and last time the subject had come up he was struggling a little, having recently gone through a divorce. Things had improved for him, as he’s now happily engaged and about to be a stepfather.

Marriage is a major financial adjustment. And marriage to a non-working spouse and bringing kids into the mix all in one swoop is financial shock therapy.

Yet John seemed relaxed.

“I have a new financial plan,” he told me.

A New Kind of Financial Plan

John told me that his salary covers the regular day-to-day expenses for his family. There’s not a lot left over at the end of the month, but he’s okay with that. All the income from his side gig goes toward retirement savings and the new house fund.

He stopped and took a puff of his cigar.

“The key for me is keeping the pots of money separate. The side gig money never goes into my primary bank account. I keep it out of sight, out of mind. And I’ll open separate bank accounts for each goal. I have one for the new house, another for retirement saving, and a third as the rainy day fund.”

There’s a term for that in the financial planning world for John’s method. It’s called “mental accounting.” Most financial planning textbooks frown on it, as they take the view that money is fungible. A dollar in one account is the same as a dollar in another account. A dollar is a dollar.

I disagree. I’m with my buddy John on this one. Having separate accounts for separate purposes can be helpful.

The Benefits of Mental Accounting

To start, it can take away your urge to spend it and force you to be disciplined. We all have our limitations when it comes to financial discipline. If hiding the money from ourselves helps us get around those limitations, then it makes all the sense in the world.

Second, keeping separate accounts allows you to better keep score. If you know you need exactly $100,000 as a house down payment, then keeping those funds in a separate account makes keeping track of it a lot easier.

The bigger story here is that my buddy got his financial house back in order after a messy divorce by being willing to hustle. He worked a second job on nights and weekends and used that second income to repair his finances.

And he continues to hustle now, using the funds to pad his savings.

Going the Distance with a Side Hustle

Some careers are more conducive to side gigs than others.

For example, John is a computer programmer. Finding lucrative side work is relatively easy for him.

But if you’re motivated, finding gigs isn’t a problem. There are plenty of sites dedicated to this. (For a list of popular sites, see here and here as a start.)

If you want to get ahead, you have to hustle. You can’t just show up at a nine-to-five job and hope for the best.

It’s really that simple. My grandfather worked at least two jobs for his entire adult life. He operated his auto glass business by day, played saxophone in a big-band jazz band by night, and usually had a few random side projects going at any given time.

Of course, you don’t have to do this alone.

If you’re married or live with a long-term partner, you can do this as a team. If one spouse makes more money than the other, make it your goal to have the higher-paid spouse’s salary cover your basic living expenses. The lower-paid spouse’s entire income can be socked away as savings, debt repayment, or to provide capital for a new business or investment.

An added benefit of this is that, should one of you decide to take a few years off to raise kids, you’ll already be accustomed to getting by on one income.

I’ll leave you with a great quote from an average movie.

The 1994 film Wyatt Earp, starring Kevin Costner, was utterly forgettable. A mediocre movie at best. But there was one line that has stuck with me all these years. When he sees his brother Virgil getting complacent, Wyatt reminds him: “There’s never been a man that got rich working on a salary.”

I couldn’t have said it better myself.

Low Risk Retirement Income with High Yields

As we head into 2020, with growing uncertainty, retirement income expert, Charles Sizemore has spent months exploring hidden corners of the market that will not only yield reliable monthly payments but are… Find Out More>>
Charles Sizemore

Income and Retirement Strategist, Charles Sizemore, CFA specializes on dividend-focused portfolios and building alternative allocations by finding value opportunities outside of the mainstream stock market.

Charles is the executive editor and portfolio manager for Dent Research's premium newsletters, Peak Income and Peak Profits.

He is also a frequent guest on CNBC, Bloomberg TV, Fox Business News and Straight Talk Money Radio, and has been quoted in Barron’s Magazine, The Wall Street Journal, and The Washington Post. He is a frequent contributor to Forbes, GuruFocus, MarketWatch and

Charles holds a master’s degree in Finance and Accounting from the London School of Economics in the United Kingdom and a Bachelor of Business Administration in Finance with an International Emphasis from Texas Christian University in Fort Worth, Texas, where he graduated Magna Cum Laude and as a Phi Beta Kappa scholar. MORE FROM AUTHOR