The Stepping Stone Fallacy

Do you ever wonder why you’ve done the things you’ve done? And why you’re doing the things you’re doing?

I’ve often thought about why I decided to go to law school.

Usually, it’s after a particularly stressful day.

I look up from the barrage of emails, case files, and notes scribbled on my whiteboard and miscellaneous legal pads and wonder who would sign up for this.

As best as I can tell, it started in high school. A time when most of us began thinking about the future. A time when something shifted in our minds from the present experience to an anticipatory existence.

No longer did we care about what was going on now, but rather our parents, teachers, and coaches started shifting our minds to the future.

“What classes are you going to take next semester?”

“What’re your plans after graduation?”

“What do you want to do when you grow up?”

Naturally, I had no clue.

I knew what I enjoyed doing. I knew what I was good at. But the only framework offered was taking that present understanding of myself and extrapolating a future reality.

I enjoyed ideas and books.

I enjoyed explaining ideas—”teaching.”

And I was exceptionally good at persuasive speaking—convincing others of the validity of certain ideas.

I excelled at debate for this very reason.

I understood the ideas for both sides and could reconcile these ideas in such a way as to simply explain why my side (whichever side that happened to be) deserved the judge’s vote.

Somehow this skill was translated into “That’s what an attorney does” and eventually translated to “You should go to law school.”

This was very much along the lines of putting the metaphorical cart before the analogous horse.

But I ran with it. Or rather rode in the cart as the horse pushed me along.

My 17-year-old self decide that I would become an attorney.

This was no longer a matter of enjoying what I was doing. This was now a matter of checking certain boxes so I could proceed to the next level up. Why? Because only when I arrived at that future could I then begin to enjoy what I was doing again. (SPOILER ALERT: this is a trap; this is the Stepping Stone Fallacy)

But here was the issue: each time I leveled up (e.g., went to college, law school, attorney job, etc.), the future shifted and imposed new requirements to reach the next level.

Even when I opened my own law firm, there became a whole new set of requirements for running a successful business: marketing, management, operations, etc.

The future goal seemingly remained the same from when I was 17, but somehow the closer I got to the goal, the further away it seemed.

In many ways, I wanted to cross a river—a metaphorical river, of course.

Here I was on one side. And I wanted to cross to the other side.

Here I was as a “non-attorney.” There I wanted to be as an “attorney.”

All I had to do was cross the river.

All I had to do was walk across the stepping stones.

In today’s age of “job satisfaction” and “career alignment,” it’s no wonder that so many millennials feel burnt out by the corporate grind.

They’re trapped on those stepping stones, never quite reaching the other side.

The thing about stepping stones is that they’re great from going from Point A to Point B, but they’re not great for questioning why Point B should be the intended destination in the first place.

Take law school for example. That was Point B from my Point A.

Had I taken the time to really question whether Point B was the correct destination, I might have arrived at a deeper conclusion that college was Point B, not being an attorney and therefore not law school.

And once I arrived there—on the other side of that metaphorical river—then I might be done crossing rivers and may want to move on to hiking mountains or navigating jungles. (Metaphorically speaking, of course, though I do love mountains).

But the issue with stepping stones is that you think you need to keep going to the next one, without questioning whether you could cross the river without them.

Take, for example, my love of ideas.

I discovered that I love ideas in college. And I knew that I loved teaching others about ideas.

But I had already started walking across the stepping stones to get to law school.

I had to keep going, right?

Well, I did what I could to procrastinate getting to the other side.

I traveled to Spain

I lived in Seattle.

I taught in an elementary school (City Year, anyone?)

I went to grad school, when my then-professor/mentor told me to go to law school, because at least then I could earn a living through my writing.

Bingo.

I was back on the stepping stones, this time with renewed purpose.

I would go to law school so I could earn a living so I could support my fascination with ideas so that I could write about those ideas on the side.

Do you see these stepping stones?

Well, as dumb as it sounds now, I didn’t realize that 80% of attorney writing is the same boilerplate language with different names and the remaining 20% can be written by ChatGPT. Go figure. (Sidebar: the real value of an attorney is being a trusted counselor and guide. More on this later.)

So what did I do?

I thought that if I could set up some “passive income” then I could leave the practice of law and finally have time to write out these ideas.

In other words, I decided to cross another river.

I started a billionaire-dollar tech start-up that never made a dime.

I drop-shipped dog toys.

I sold digital products.

I taught an online course for students interested in law.

I even ran a house-cleaning company for a few months.

And you know what happened?

I was no closer to crossing that river than when I first got started. The stepping stones would multiply and then disappear in a cyclical fashion.

After all these attempts at starting a business, I finally opened my own law firm and by the grace of God, the firm has been successful.

But even now, there are more stepping stones to cross before reaching the other side of a “fully automated” business—a former dream of mine that several attorneys seem to have achieved.

However, I finally got to the point where I realized I was doing all of these things so that eventually—maybe—one day—I could sit down and explore more ideas.

But then it hit me: I didn’t need all of those stepping stones. I could just step across the river and begin writing.

In The War of Art, Steven Pressfield calls this type of distraction or procrastination—what I’m calling stepping stones—“Resistance.”

Resistance—in its most heinous form—says you need to do X, Y, and Z before you can do the thing you’re actually called to do.

For me, that looked like I needed to go to law school and then earn passive income and then grow a million-dollar law firm before I could sit down in front of a white screen and punch on plastic letters until a coherent idea arrived on the page.

As ludicrous as this seems now, I do not doubt that there are several other people who have this same framework running through their minds—unbeknownst to them.

That’s why I called this framework the Stepping Stone Fallacy: just because you’ve been crossing these metaphorical stepping stones does not mean (1) they are the right stones to be crossing or (2) that you cannot simply step over the river and get to where you actually called to be.

So here’s my encouragement for you:

Live out your calling.

Do the thing you are called to do and soon you’ll become the person you’re called to be.

Don’t focus on the stepping stones; question the size of the river.

And if you’re a writer, then by golly—write.