The Closest Thing To Career Insurance: How To Start and Maintain A Profitable Side Hustle

Image for post
Image for post

Have you been wondering what you’ll do when age discrimination messes with your career? Or wish there was such a thing as “career insurance?”

The closest thing to protecting your livelihood may well be a side hustle.

A side hustle is a way to make extra money outside your regular day job. If you don’t have a day job, your side hustle can be a way to make money while you look for a full-time job.

Your side hustle can be the closest thing to career insurance. Suppose you get laid off, or you just wake up one day and realize you dread going back to work. Instead of wondering, “How will I pay the bills?” you simply turn to your side hustle. If you don’t have a side hustle, you decide to start one.

Some people keep their side hustle on the side; they eventually land a full-time job but keep their side hustle as a way to maintain a creative activity.

Others find a way to turn their side hustle into a full-time job. It can also be your true passion — a chance to delve into fashion, travel, or whatever it is you care about the most without quitting your day job.

Image for post
Image for post
Photo by Brooke Cagle on Unsplash

You’ll find lots of articles and lists online: “101 ways to make money with your side hustle.” Usually, they’re a big laundry list of every possible side hustle gig you could imagine. So how do you choose? A lot of people just give up at this point because they can’t decide.

Narrow your options based on these 3 criteria:

If you’ve never sold or owned a business, it’s a good idea to test the waters before making a long-term commitment. I’ve had clients who thought they’d love being a life coach, only to find they get bored listening to clients hour after hour, day after day. Some people decide they won’t be consultants after working with clients who make decisions by committee and never follow the advice they paid for (which means they won’t be giving you helpful testimonials or referrals).

Successful entrepreneurs talk about taking small steps so they can “fail fast” and move on to the next thing. You learn from each failure.

When I first started online, I’d just published a book on dealing with relocation stress. It seemed logical. People hate to move. They need help. I’ve got solutions.

But I soon learned that people weren’t used to the idea of getting coaching or consulting help for a move. And I had to be careful to clarify that I’m not a therapist, even though we’d talk about stress. Soon I converted the site to a career change business, which was much more successful. I did get clients who wanted to talk about moving, but in the context of careers and career change.

Image for post
Image for post
Photo by Hive-Boxx on Unsplash.

The site brings me clients and sales to this day. And my book on moving continues in the third edition on Amazon.

You know people will pay to solve the problem that will be the basis of your business. But how do you get those people to become your clients? This is the single most important question to ask yourself.

All too often, people follow the misguided advice to “leap and the net will appear.” I actually got this advice myself.

Occasionally the net does appear after you leap — usually because you’ve managed to land on a sweet spot.

Image for post
Image for post
Photo by Joshua Ness on Unsplash.

You can’t count on that sweet spot occurring for anyone after you — and you can’t expect to follow someone else’s sweet spot.

If you don’t have sales experience, try to get some while you’re still on someone else’s payroll. But if you still have no sales experience, don’t give up. Just be aware that you’ll need to change your mindset and maybe learn some techniques.

Getting high-end corporate clients often requires you to network and make presentations to committees. Getting one-on-one coaching clients might require you to set up “get-acquainted calls,” which are really opportunities to sell.

On the other hand, some people attract clients by webinars, recorded presentations, speaking, blogging or other methods that aren’t directly involved in personal selling. You do need to learn how to use the Internet to attract clients who will resonate with your offer.

Pick a side hustle where you know there’s a great deal of evergreen demand and where it’s easy to gain credibility. Examples include pet sitting, dog walking, becoming a virtual assistant, editing, or bookkeeping.

Don’t dismiss any of these fields as too “menial” or “low-level.”

People who begin in these fields often earn far more than they anticipated; sometimes they find themselves moving into more high-end fields.

One successful copywriter began her career as a virtual assistant. A journalism major in college, she was delighted when a client asked her to revise a sales letter. When her letter out-performed the control, she knew she had a new career. She became an internationally recognized copywriter and copy trainer.

A college student began walking dogs to pay for her tuition. After she became a special ed teacher, she kept up her side hustle. When she realized her side hustle was bringing in more revenue than her more prestigious day job, she went all in.

Now she has built an empire with people working for her. She earns well over six figures annually…with no expenses for a business wardrobe.

dog-walking can be an excellent side hustle for new entrepreneurs
dog-walking can be an excellent side hustle for new entrepreneurs
Photo by Humphrey Mulaba on Unsplash.

If you’re still employed, check your employer’s requirements, both formal and informal. In some companies, there’s nothing on the books but you’ll be ostracized (or worse) if your boss suspects you’re going entrepreneurial.

Some corporations want 110% of your time and attention and will be jealous of any competing activities. I once read a news story about a couple of people who were fired after taking entrepreneurship courses at the local college.

Do you have family or friends who will be supportive? Or will they attack you with, “Who do you think you are? You couldn’t even sell Girl Scout cookies!”

There’s a saying that entrepreneurial life means doing what nobody else wants to do for a period of time, so later you’ll be able to live the kind of life everybody wants to have.

So for a short time (believe me, it’ll seem longer) you may have to carve out space in a crowded day. You’ll be saying “no” to invitations and requests for help. You might have to negotiate with family and friends to clear the decks; I’m not a family therapist, but I’ve met many people who chose to work with one during this time.

In particular, try to clear the decks for some focused time when you won’t be interrupted.

Ideally, create a physical space where you can work comfortably, where you don’t use the space for anything else. You may be able to convert a guest room into a home office. And a surprising number of people work from a corner of their living rooms or at the end of a dining room table.

home office for your side hustle for your career change
home office for your side hustle for your career change
Photo by Nikola Balic from Unsplash.

Some people also use odd moments during the day.

When you’ve got an hour here and there, that’s time you could use to build your side hustle. Carry a tablet or smartphone so you can use waiting time. Listen to podcasts or training materials during your commute or when you’re stuck in a waiting room.

One woman commuted to work by car each day. While she was preparing to become a life coach, she would coach clients from the passenger seat of her family car, while her husband did the driving. (You can listen to her story on this program. Use this link to get a $20 discount.)

“But I’m tired at the end of the day,” you might be thinking. “I need to relax.”

It’s a common challenge. Some side hustlers change their routines to add energy after work. They stop by the gym, walk the dog, go for a run or exercise at home. They eat lighter dinners and sometimes skip dessert (or save it for a treat on the weekends as a reward for a successful week).

And the big surprise: they often find they’re newly energized when they sit down at the computer. Once they start working, the adrenalin kicks in. They have to make sure to stop in time to get a good night’s sleep. (You probably know the effects of sleep deprivation on productivity; I’m not a doctor but I believe in sleep. LOTS of sleep.)

Two bonus tips:

(a) Have a plan. One of the biggest sources of procrastination omes when you’re not sure how you’ll use your work time. Know what you’ll do when you find yourself in your workspace.

(b) Find a coworking space. Nowadays they’re everywhere! If your city has more than one, visit two or three to see where you’re most comfortable. Some have a reasonable drop-in day rate; some require you to sign up for a minimum time. Some are open late at least one night a week; some are open weekends; some have “free” days when you can come and work free, even if you’re not a member.

A coworking space gives you a place to work that’s free of your usual distractions. As a bonus, you’ll likely meet many self-employed members at different stages of their business life.

Recently I worked with a client who needed help with her resume as she sought to change careers. “I’ll help you,” said a manager who’d been her boss early in her career. “You don’t need to pay for a career counselor.”

By the time my client reached me, she’d wasted several months with her outdated, unfocused resume. She was astonished at the difference between his “advice” and her consultation with me. I began by asking her several questions about her goals and her experience; he never did.

My rule of thumb is, pay for advice but get information for free.

If you’re wondering, “Should I pursue a new career as a web designer?” a business coach or career coach will help. But if you get a chance to talk to some real, live web designers, ask them for information. You might ask, “What kind of credentials do you customers ask for?” or, “What is a web design portfolio and how do I get one before I get clients?”

Insist on getting answers based on their experience, not their opinion. Instead of, “What mistakes should I avoid?” ask, “What’s been your biggest challenge — the thing that almost made you give up the whole idea of being a web designer?” Or, “What’s your biggest frustration on a day-to-day basis?”

side hustle for career change — where to get career coaching
side hustle for career change — where to get career coaching
Photo by LinkedIn Sales Navigator on Unsplash.

Some people ask questions like, “What would you tell yourself if you were starting out today?” That’s a trick question: you’re actually asking your interviewee to speculate. And today’s quite different from yesterday.

When I interviewed a dozen successful business owners who had pivoted from corporate to entrepreneurial roles, I expected them to talk about websites and sales goals. Instead, every single person emphasized mindset and intuition. Every one.

Would you like to get a sense of how people really start, sustain, and grow their side hustle?

I interviewed twelve people in different fields who made the tough transition. You can listen to the recordings of all 12 plus enjoy some bonuses. If you took each of these people for coffee you’d pay much more than you’re paying for the program, if you could find them and get them to agree to spend an hour with you. Get immediate access to all the interviews with a $20 discount. Click here.

Or you can go to the sales page and use the coupon code HUSTLE20 to claim your discount.

You can also schedule a one-to-one consultation so we can discuss your own path to self-employment (or other career goal). Click here to schedule a consultation.

Originally published at on September 2, 2020.

Helping entrepreneurs and independent professionals grow their businesses one story at a time.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store