4 min read

Introducing the Side "Step" Hustle

Illustration of the Side "step" Hustle

Nothing delayed my transition to self-employment more than the fear of some giant income chasm between executive paycheck and the equivalent (eventual, hopefully) business income.

The recurring feeling was that I had passed a point of no return in lifestyle and family financial commitments. That I could not risk having less income or potentially no income for any period of time while building some "dream business". I was stuck.

After all, I did NOT have:

  • A "banked win" from some big equity liquidity event or investment paying off sitting in the bank
  • Substantial savings, say 12-18 months of executive-level-salary savings in the bank, nor the financial bandwidth to build that quickly
  • Some inheritance windfall of cash, etc.

Side Step: Start by Doing What you Already Do

So, this is how I did it: I realized that doing what I "already do" at my regular job had the most potential for a quick ramp-up of revenue and thus was the quickest path to being on my own. Unstuck. Free to dream and build.

  • Is what I did in my career my dream business? No.
  • Is it for the long term? No.
  • Is it something I'm already good at and creates a ton of value for others? Yes.

Well then, that would unlock the path to a dream business and get the right flywheels spinning... even if I didn't quite know what that dream business would be yet.

Traditional Approach. Try to chip away at building your "dream" business while still slogging it out at your full time "big job". This will go on forever and is a very tough road.

Have your business initially be what you're already basically doing in your career. Switch to this track first. Then work on the transition to whatever your dream business is.

Side "Step" Approach. Make your first business familiar work that you already do at your day job. This sets you up to build your dream business a little later.

I call this move the side "step" hustle because it puts you into self-employment earlier, even if it's doing essentially the same work you've always done.

Why Would Someone Ever Start Their Entrepreneurial Journey Doing the Stuff They Do At Their Regular Job?

Wouldn't I just stay at my secure job and chip away at my dream business? Why take the risk if it's doing the same shit I'm doing at my "secure" day job? I thought the same thing. For months. Here's why:

  1. You probably have a family and a mortgage. Maybe some college tuition and car payments. You've gone way, way down a path of a high-earning professional employee and you need to replace that income, ASAP. Offering your current career skills is the quickest way to this level of independent income.
  2. You're forced to learn hard lessons that you only learn on your own, as early as possible. How to ask for money. How to price things. How to sell. Value vs. Time/Effort/Busywork. Results vs. "Trying your best". We will talk about so much of this in the future.
  3. You'll learn a ton about other companies and how they work. As you pick up clients and work with their organizations you're going to see 100X the amount of problems that could be solved and different ways to solve them than you would at your regular job.
  4. Building your support team early: You're going to need an accountant, a lawyer, potentially a career coach and a therapist. Meeting these people and establishing these relationships, pressure testing systems, etc. ASAP is key.
  5. When the student is ready, the master appears. Your "on your own" mindset is going to unlock inspiration that you'd NEVER encounter working at your day job in and out. This is a little woo woo but it's totally true. For example, I never would have thought about this publication idea without being on my own for a little while.
  6. You instantly increase your "luck surface area". By being out there on your own, you're going to be making connections and having conversations you would never have had trying to sneak around on your own while being employed full time at a job you despise. It's amazing how many opportunities have sprung out of nowhere simply by being out there on my own.
  7. Moving and doing NOW vs. sitting and pondering.

An Example Scenario

VP of Software Engineering wants to start a fun, artsy T-Shirt Business. Going from VP to T-Shirt Business seems impossible. Their $200K salary is equivalent to a lot of success selling humorous artsy garments. A lot, say 300 T-Shirts a week minimum. Meanwhile the day job is all-encompassing. Seemingly impossible chasm to cross initially. How would they use the side "step" method?

  1. Build up some programming side work while working as an employee
  2. At 80-100% of current salary from side work, quit job, transition to full time programming freelancer/consultant (Side Step)
  3. Learn how to run a business and build momentum, build support team, increase luck surface area, start T-Shirt business gradually
  4. Transition to full time dream T-Shirt business