How to Work in the Gig Economy and Still Save Like a Corporate Lifer

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Wealthsimple is a whole new kind of investing service. This is the latest installment of our “How To” series, where we lay out smart and easy-to-understand advice on navigating the financial world.

So you’re self-employed. Congratulations! Now you can go to the gym at 3:30 p.m., when no one’s there. Braise a pork shoulder on Tuesday afternoon and actually make it to your kid’s performance of “Third Graders Sing the Lady Gaga Songbook.” (You can also nap. Not that you'd ever do that.) As long as you can fight off the specter of loneliness by talking to the cat all day, there are many benefits to the gig economy.

Retirement savings isn’t one of them.

I should know. I’ve been working freelance for half a decade now, and while I certainly don’t miss the soul-crushing fluorescent lighting or the draining commute of my desk job, I sure as hell do miss that 401(k) match.

It’s hard to be a financially responsible adult without a benefits department.

That’s why we’re here. To help design a plan that a freelancer can actually stick to, we enlisted the help of some experts: Jonathan Medows, founder of CPA for Freelancers; Paul Golden, a financial expert at Smart About Money; and Hersh Shefrin, a behavioral finance guru and professor at Santa Clara University’s Leavey School of Business. Here’s their road map (with a little editorializing from yours truly).

First Things First: The Rainy-Day Fund

The only good reason to go freelance without enough cash to cover at least three months of living expenses is because by “going freelance” you mean you “got laid off.” Experts recommend six months as the gold standard, but you absolutely need three. Remember: Regular paychecks may be a thing of the past. And even if you know you have a payment coming, that doesn’t mean you know exactly when that payment is coming.

Keep this reserve relatively liquid — and don’t keep it in even relatively risky investments. A savings account will do the trick.

Remember the 30 Percent Rule

Don’t go all googly-eyed when you see your first freelance check. Remember: Taxes aren’t taken out. Accountants recommend squirreling away 30% of each check for taxes—which you’ll most likely pay quarterly. Set up a separate savings account that’s only for taxes. And remember: Don’t touch that money, it’s not yours!

Get Obsessive About Your Spending Habits

This is a personal thing for me, and I’m serious about it. The gig economy—in which you have multiple irons in multiple fires seven days a week—can get very complicated very quickly. If you don’t physically write down exactly what you’re spending money on, you’ll never be able to figure out why you can’t save for retirement. And then you’ll think: I’ll just do it later. And then it’ll be later, and you’ll be screwed.

So get Quicken or Mint or whatever money-management software du jour you like—I prefer a good old-fashioned spreadsheet—and comb through bank and credit-card statements to get an idea of where your money goes.

“Look, you may think that you don’t have money to put towards savings, but if you look closely at where your money is going, chances are you’ll see some opportunity,” Paul Golden, of Smart About Money, says. “Take your time and do it over a couple of months—it’s tedious, but our spending habits vary.”

Then Set a Budget

Everyone’s budget will be different, but there are some guidelines. For instance, if you’re renting, a good rule of thumb is to try to keep your rent under 30% of your monthly income. And when you’re making that budget? That's when you can build in savings — for retirement and for life. And, about that...

Now the Important Part: Decide How Much You’re Going to Save

Before we go on, let’s set the first priority: to max out contributions to your retirement account. The limit for an IRA per year is $5,500 ($6,500 if you’re over fifty). The limit for a Roth IRA each year is $5,500, but that’s on a sliding scale tied to your income. The limit on a SEP IRA is higher: It’s either 25% of your income or $54,000, whichever is lesser. If that's confusing, your accountant should be able to help. (Which one’s best? More on this in a moment.)

But the first step is to set up an account right now, so you have no excuse not to contribute to it. (And Wealthsimple has recently launched, we humbly submit, the best, simplest version of the SEP IRA. Get started here.)

If you earn enough to have maxed out your desired retirement account and can still have more you can save, it’s time to open a taxed investment account.

Take Away Temptation: The Importance of Automatic Deposits

First, make it a priority to set aside a portion of every check you get. Jonathan Medows says 10% is a good place to start; you can ratchet up that percentage as your annual income (hopefully) increases. “Our aspiration is 25%,” he says. “That might not be realistic in the short term, but remember: You need a lot of money for retirement.”

But don’t pick a number that’s totally unattainable. “Don’t bullshit yourself,” Medows says. “That’s my first rule. Decide on a percentage that works for your income and living expenses. Then it’s a matter of discipline, to a certain extent.”

Again, the key is to take it out automatically, just like an employer would. If you have a semi-regular gig, and know for certain you’ll make at least a certain amount each month, set up an automatic deduction through a firm like Wealthsimple. Take the decision out of your own hands as much as possible.

Trick Yourself, Psychologically, Into Being Better at Saving

You think you’re bad at saving, join the club! It’s human nature. A nice bottle of rye feels far more thrilling than putting forty-seven dollars into your retirement account. But we’re here to tell you that there are tricks to beat your inner spending demons.

“At their core, people are vulnerable to self-control issues. The desire for immediate gratification often overwhelms the need for long-term planning,” Hersh Shefrin, the behavioral psychologist, explains. “The most effective way of dealing with that issue is to use what are called external roles.” External roles are essentially people or things that are not you, but that makes you do the thing you want to do. They work because they remove discretion and minimize the need to have to repeatedly face temptation and overcome it. Your employer taking out money for your 401k every month is an example of an effective external role. “In a gig economy, it’s harder to get external roles,” Shefrin says. When you work for yourself, no one’s making you do what’s good for you, so you have to force yourself.

How do you introduce external roles into your spending habits? Here are two “games” you can play.

Make Yourself Use Cash

This is a way to make spending money more painful. Paying right away, and watching your reserves deplete, isn’t that fun. Shefrin also recommends paying for things with the largest bill in your wallet. “That forces you to think, ‘Well, do I really want to break a large bill in order to have a particular expenditure?’ So that’s a way of saving: by cutting down your consumption as opposed to purposely taking some of the income off the table.”

Now introduce a little pleasure to the savings part of the equation. “When you pay for stuff in cash,” says Shefrin, “and the change is five dollars or less, put that in whatever your version of a piggy bank is and let it accumulate over a month or so. And then go deposit it. That feels pretty good.” This is obviously not going to be enough to set you up in a Tuscan villa for an early retirement, but it accomplishes two things: tricks you into spending less on impulse purchases and forces you to put all that five-dollars-and-under change—which will add up quicker than you think—right into savings. Which will make you want to save more.

Turn Savings Into a Game

This might sound goofy, but stick with us. Shefrin is one of the world’s leading behavioral economic experts, after all.

“Gaming is really the key, because it gets your brain to turn on the reward centers,” Shefrin says. “If the reward centers are driving your behavior rather than fear, then it’s likely that you will act.”

One easy (and, fine, kind of elementary!) way to do this would be to pick an attainable number for your retirement savings and then reward yourself quarterly with a nice night out or an obscenely expensive pair of jeans you’ve been coveting for months.

“Just make certain that you structure the game so that it’s winnable, and then you can get the treat. You’ll also need to be tough on yourself—if you don’t save, then you forego the treat, whether it’s a restaurant meal or something fun you were planning for the weekend, or whatever it is that is pleasurable,” he says. “People respond really well to game environments.”

And Where’s All That Savings Going? Pick the Right Kind of Retirement Account

Ah, yes: the million-dollar question. (Literally. If you want to save a million dollars, that is...) In most cases, there is a very simple answer: the SEP IRA. The government may screw over freelancers in many ways—lack of protections, zero recourse for consistently late checks, a virtually nonexistent social safety net—but they do offer a fairly reasonable retirement-savings program!

Unlike a traditional IRA (which maxes out at $5,500 annually), the SEP IRA—Simplified Employee Pension Plan (not Self-Employed Pension Plan, as you might have thought)—allows you to contribute up to 25% of your net income (with a maximum of $54,000). It functions like a traditional IRA: your contributions are subtracted from your income before taxes; your withdrawals will be taxed upon retirement. (How much you can deduct for income tax purposes varies. You can do the math here.)

You have until tax day to contribute, so technically you can put everything in the day before. But the smartest way to invest is on a regular weekly or monthly schedule—that way you don’t put yourself at risk of buying all your investments at the top of the market. (If you want to get fancy, this is called dollar-cost averaging.) That’s another advantage of automatic deposits—you don’t have to remember to make contributions on a regularized basis.

Now go on, get saving!

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Money Diaries


Margaret Atwood


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