The Dirty Little Secret About Side Hustles That Nobody Wants to Talk About

It’s 2018 and the Side Hustle Revolution is officially here (and has been for a while). If you’re a Millennial living in a major metropolitan city, chances are you know someone who earns money on the side to supplement their full-time income.

Sounds pretty awesome, right? I mean, who couldn’t use another a few hundred or better yet, thousands of dollars per month?

After all, that Ferrari, Gucci bag, or five-star vacation isn’t going to pay for itself.

Want more of that green stuff? Start a side hustle.

Being the overachiever you are, you probably started googling terms like:

  • “side hustle” — 14,554 searches per month
  • “sidegig” — 8,100 searches per month (do people really type in “sidegig” as one word? My faith in humanity just dipped a bit…)
  • “how to make money on the side” — 6,627 searches per month


You probably found articles that fell into one of three categories:

  1. Side Hustle ideas — while helpful, it usually results in nothing more than “idea porn” (whimsical fantasies that never become a reality)
  2. Case studies of successful side hustles — while inspirational, this can also drag you down with self-doubt (I mean, there’s no way YOUR side hustle could achieve this, right?)
  3. Why you need to start side hustle — tell me something I don’t know already..

After carefully researching dozens of the most popular articles on side hustles, 99% of the content ignores a critical part of the equation:

How do you start and stick with a side hustle until the moolah appears?

Not the actual marketing/sales tactics or growth hacks, but on a deeper level, how do you set yourself up for success by embracing new habits and leveling up your productivity?

By definition, a side hustle squeezes in between your full-time job and everything else (sleep, exercise, friends, family, and Netflix).

When you combine a limited window of time with often inexperienced, first-time solopreneurs or freelancers…

…it’s the perfect storm for another one of those “tried-this-but-didn’t-work-so-it’s-not-for-me” stories.

Still, why is it that some people find time to earn extra income on the side despite demanding (and even high-paying) jobs, and others don’t…even when they need it more, have more free time, and already have the “perfect idea”?

If you think you need more motivation, willpower, or self-discipline, then you’ve already lost.

Here is a three-step system rooted in behavioral psychology that will give you the kick-in-the-ass you need to launch and grow your first side hustle.

Step #1: See Yourself as a Side Hustler

Change is hard (I know, shocking right).

It doesn’t matter if you’re looking to get into better shape, start a business, or just simply spend more time with your loved ones…

…fleeting moments of inspiration are difficult to put into practice and even tougher to sustain.

Most people strive for change like this:

  1. Dammit, I really need to start a side hustle this year.
  2. My goal is I’m going to earn $500 a month in side income by March.
  3. Let’s do this! I’ve read a bunch of how-to articles, found my perfect idea, set up my website, and am ready to start making money online!
  4. FML…it’s been a month, and I haven’t made a single dime yet…
  5. I’m just not feeling it today. I mean, I deserve to relax after a long-day at the office…wait…new Black Mirror episodes? Let me just watch one for now…

Setting goals is usually enough motivation for people to start taking action on them, but it’s difficult to stick with new behaviors.

Most goals are based on performance.

Performance goals are great for pushing you to the next level of habits you already do.

Running faster, lifting heavier weights, improving your relationships…all things that most people can achieve with the right goals.

But they’re not so helpful when it comes to creating new habits…

…such as starting a side hustle that requires a shift in your nights and weekend routine.

Goals, inspiration, and willpower simply aren’t enough.

Enter Identity-Based Habits.

According to this article from An International Journal for the Advancement of Psychological Theory:

Identity-based motivation theory (IBM), a social psychological theory of human motivation and goal pursuit, explains when and in which situations people’s identities or self-concepts will motivate them to take action towards their goals.
People interpret situations and experienced difficulties in ways that are consistent with whichever identities are currently on their minds, and prefer to act in ways that are identity-consistent rather than identity-inconsistent.
When actions feel identity-consistent, difficulties that come up tend to be interpreted as important, suggesting actions are meaningful. On the other hand, when actions feel identity-inconsistent, the same difficulties suggest the behavior is pointless and “not for people like me.”

In short, people are more inclined to act in ways consistent with their identity and less inclined to act in ways inconsistent with their identity.

I used to struggle to maintain a consistent workout regimen.

My goal was to hit the gym at least 4x a week, but it ended up being more like 2–3 times a week (once during the work week, and once on the weekends).

Now, I work out 5 times a week and rarely break that streak (even when I’m on vacation and there’s no gym nearby).

What changed?

I started telling everyone around me (starting with myself) the following statement:

“I’m the type of person who takes pride in working out consistently so I can feel confident about my physical appearance”.

It became part of who I was.

Back when I first started telling myself that, I didn’t have a system in place for eliminating willpower from the equation (see tip #2 below).

So there were days when I didn’t feel like working out and hemmed and hawed over skipping (after all, it’s just ONE workout, right?)…

…but then I would feel this wave of guilt that washed over me…

…reminding me of who I was and how much I valued looking and feeling my best.

That was enough to get my ass to the gym just about every single time.

The more I went, the more it reinforced my identity, and the easier it was to keep it up.

It might feel a bit weird at first, but with a few small wins under your belt, you’ll be surprised at how quickly and easily it becomes part of the new you.

So how can you apply this to starting your first side hustle?

Here’s how to form an identity-based habit:

  1. Decide on the desired result.
  2. Link the desired result to the type of person you want to be and add a pleasure-based reward.
  3. Prove it to yourself with small wins.

The key here is to start with small steps. Over-exerting yourself will only sabotage your efforts.

For starting your side hustle, create something like this:

  1. Desired Result: Earn at least $1,000 on the side each month.
  2. Identity + Reward: I’m the type of person who earns extra income on the side so I can afford to take vacations every year (replace with whatever reward you feel most excited about)
  3. Small Win: Spend one hour a day every Monday, Tuesday, and Wednesday night cold emailing potential clients with your offer.

Pro Tip: Schedule it on your calendar and set a reminder (at least for the first 4–6 weeks).

Focus on being the type of person who earns extra income on the side and repeatedly proving it to yourself until it feels weird not to work on your side hustle.

When you start seeing the extra money come in, it’ll be something you’ve anticipated happening because, well, that’s just who you are.

Step #2: Create a Realistic Side Hustle System You Can Commit To

Here’s another method for starting and sustaining behavioral change over an extended period.

When you stack this with identity-based habits, change not only becomes easy, but borderline mandatory (your self-image won’t accept anything else).

Let’s use another real example from my life.

I noticed that despite working out 5x a week, I wasn’t achieving the desired physical transformation.

Bruh…where the six-pack at?

I realized that I was sabotaging myself by not eating a balanced diet optimized for shedding stubborn fat and gaining lean muscle.

Whenever I got hungry, all my healthy eating habits went out the window and got replaced with wings, pizza, burgers, Chinese take-out, etc.

Chinese food hits the spot when you’re starving…

I mentioned this to my personal trainer at the time and he promptly replied “abs are made in the kitchen”.

He immediately put me on a meal plan consisting of 6 oz protein, 4 oz veggies, and 4 oz carbs.

More importantly, he recommended a meal delivery service that could customize their meals to fit that plan.

I started seeing results very quickly.

What changed?

I created a consistent, repeatable system (or process) for getting in shape and transforming my physique.

It looked like this:

Goal: Cut excess fat, build lean muscle, look good shirtless


  1. Work out 5x a week between 2:00PM–3:30PM each day
  2. Only eat meals from the meal delivery service during the week (I let myself cheat on the weekend)
  3. Consistently improve workout intensity (heavier weight, more sets/reps, less rest, etc.)

If I had continued to just focus on my goal, I would’ve easily gotten discouraged with my limited progress.

I instead created a system that would support a nutrition-based, exercise-oriented lifestyle that was sustainable.

As long as I checked my progress from time to time, I cared less about the actual results and more about not missing my workouts and eating the right meals.

I knew that if I kept this up, I would eventually hit my goal of transforming my body over the long-term …

…and more importantly, I’ll be able to keep my new physique because I now enjoy the process.

Here’s how you would apply this to starting your side hustle.

Goal: Earn at least $1,000 a month on the side.


  1. Send 20 personalized cold emails per month pitching potential clients that are willing and able to afford your services.
  2. Take on one new client per week, even if you have to do it for free, as long as you get a killer testimonial or case study out of it (and they share it with at least three other people in their network who could use your help).
  3. Post FB updates with new client testimonials as they come in each week.

Assuming you have an offer that delivers valuable results to your clients, focusing on consistently executing this system will virtually guarantee new clients an earning at least $1,000 per month on the side.

Remember, goals are about the short-term result. Systems are about the long-term process. In the end, process always wins.

Step #3: Remove Motivation and Willpower from Your Side Hustle

Let me know if this sounds familiar.

You start the work day with every intention of going to the gym afterward….

…but after a particularly stressful, sloth-like day at the office, you find yourself headed to the bar for happy hour…

…and your evening workout quickly fades into oblivion.

Where did the “gonna-go-beast-mode-in-the-gym” version of you go?

Roy Baumeister, a psychologist at Florida State University, calls this “ego depletion,” and he proved its existence by conducting the following experiment:

He sat a group of students next to a plate of fresh-from-the-oven chocolate-chip cookies.

Some were allowed to snack away, others ordered to abstain.

Afterwards, he asked both groups to complete difficult puzzles.

The students who’d been forced to resist the cookies quickly threw in the towel….their willpower was zapped.

The cookie eaters, on the other hand, had conserved their willpower and worked on the puzzles longer.


Up until now, we’ve been talking about using identity-based habits and systems to start and build your side hustle…

…notice how there was no mention of self-discipline, willpower, or motivation.

That’s because willpower is unreliable at best and a honey trap at worst.

You wake up motivated to work on your side hustle at night….that is, until 6 PM hits after a long day and out of nowhere comes happy hour followed by Netflix binges.

Take a moment to think about what areas of your life do you find yourself struggling with willpower?

Hint: it’s usually when there’s a red-hot, emotional mental battle happening between taking action A (which you should be doing), but finding yourself giving into action B (and then rationalizing it with a convenient excuse).

A: Going to the gym

B: Going to happy hour

Rationalization: I deserve it after a stressful day.

A: Eating healthy, balanced meals

B: Stopping by the pizza place down the street on your way home from work.

Rationalization: I’ll make up for it at the gym tomorrow.

A: Working on your side hustle

B: Netflix and chill

Rationalization: I’ll work on it over the weekend.

Imagine what it would be like to cooly observe and acknowledge your impulses…

… without giving into them or having a heated debate with yourself.

It’s not about ignoring these warning signs. They’re always going to be there.

But you need to treat them like a difficult question during a presentation at work — acknowledge it but remain in control of the destination.

Start with small wins. One of the “A’s” above at a time. Silence the inner mental battles.

Notice how what used to get you all hot and bothered no longer has the same hold on you….your emotions stay in check because you know how this game ends.

Setting Yourself Up for a Successful Side Hustle

Starting a side hustle is an intimidating endeavor.

Not only does it challenge you to take direct responsibility for your income, but it also involves an underrated aspect you might’ve never confronted head-on — embracing new behaviors and doing hard work without a guaranteed reward.

  • Work hard at the gym — see visible results relatively quickly
  • Get an MBA — get access to high-paying job opportunities
  • Surprise your significant with a unique gift or experience — strengthen your relationship

When starting your first side hustle, it could take weeks or even months before you get that first client, make that first sale….and even longer before you hit your desired income goal.

It’s easy to get discouraged and quit, especially when you’ve got a full-time paycheck and your basic living expenses are covered — rent, food, bills, etc.

This is the secret nobody wants to talk about — starting and sustaining a new behavior that supports your journey to the promised land.

Ideas, tactics, strategies, case studies, motivational Instagram posts or YouTube videos…they’re all fine and dandy.

None of it will mean a thing after you’ve sent out your first 50 emails, got three responses, and earned zero dollars….

…and the poison of self-doubt slowly starts creeping in:

“You know what, I’m not the type of person who can earn income on the side. Who am I to start an online business? I’d rather just focus on finding a new job, switching careers, or getting an MBA”.

I’ll end with a bit of practical motivation for those of you on the fence.

The extra cash you earn on the side can mean the difference between barely squeaking by or having money to go on vacation. It could mean paying off that $15,000 in credit card debt or building a secure emergency fund with 3–6 months of living expenses.

Most important of all, it could mean having the peace of mind knowing you have the skills and abilities to earn money on demand.

With recent reports showing wages have barely grown during the eight years since the Great Recession and more than half of Americans having less than $1,000 in savings, there is no better time to embrace the side hustle.

Before you throw yourself into building your dream business, make sure you commit to the process and who you become as a result of it…

…and the rest will take care of itself.