The Long-Run Is More Attainable If You Do These 5 Things

Declan Wilson
Photo: The Lazy Artist Gallery/Pexels

When I left my full-time job in 2017, I was a kid in a candy store. My day was no longer filled sitting in a drab cubicle. Instead, I was free to become the digital entrepreneur of my dreams.

With 8 extra hours in my day, every day, I was going to accomplish so much.

All I had to do, the gurus said, was show up, follow my passions, and meditate or something and everything would fall into place.

How wrong they were. After, leaving my 9-to-5 I…

  • Launched a coaching/membership business. That imploded.
  • Tried daily vlogging on YouTube. That fizzled out.
  • Gave everything up at one point and tried to only be a stay-at-home dad. That got boring.

Various other projects and ventures ended the same way, I either got bored with it or gave up when things got tough. Each one left me with a pit in my stomach, wondering: Was I cut out for life outside a traditional 9-to-5 career?

The hardest part about leaving your job to build your own career isn’t the uncertainty, nor is it the brutal reality of being an entrepreneur, it’s sticking with something long enough to see results.

What do woodpeckers and pennies teach us about the long-run?

If you’ve ever launched into some new project or took the leap and tried starting your career from scratch, you’ve probably experienced the woodpecker-conundrum.

“A woodpecker can tap twenty times on a thousand trees and get nowhere, but stay busy. Or he can tap twenty-thousand times on one tree and get dinner.”
— Seth Godin, The Dip

Jumping from tree to tree hoping for easy results isn’t the strategy of an entrepreneur. As Mr. Godin puts it in his analogy, it’s a great way to stay busy, but go hungry.

However, what if we took the woodpecker-conundrum and looked at it from another angle. Instead of grub, it’s pennies.

Let say Day 1 of entrepreneurship you earn $0.01. The next day it doubles to $0.02. The day after that you earn $0.04. Every day you show up, your revenue doubles.

By Day 10, you’re still only playing for pennies. It’s frustrating. How long until you give up and start pecking away at another tree?

This is what it feels like for most of us. We show up, we put in the effort, and nothing seems to happen. I left my full-time job three years ago and I still feel this way.

However, if you plot the double-a-penny situation on a graph, this is what it looks like over the course of a month:
Image by author

On a literal level, this demonstrates the mathematical power of exponential growth. On a practical level, this shows the power of sticking it out.

Me and you, we’re only on Day 5. We aren’t even going to notice anything has changed until a tiny blip appears on Day 23. Before we know it, we’re millionaires by the month’s close.

So what do woodpeckers and pennies teach us? They teach us that building something valuable takes time. It takes slugging it out day after day for a very long time with little reward. It takes grit.

But how do we do this?

I have a plan.

How to stick it out in the long-run

If you want to go pro, you need to learn how to stick it out past Day 5. You need more than someone telling you to show up and stay patient.

We’re going to be playing for pennies for a while, so whether you want to make it as a writer, or an entrepreneur, or anything this crazy world has to offer, we need a plan to make the long-run more bearable.

Here’s my plan in a nutshell:

  • Eliminate any distractions in your life that induce envy
  • Think in longer chunks of time
  • Measure your progress but don’t dwell on it
  • Find external motivations to keep you going
  • Have a plan in place for the windfalls

Let’s look at these one-by-one, shall we?

Eliminate Envy

I know life is not a zero-sum game. There’s plenty to go around.

When I see other online writers cashing in, I’m genuinely happy for them, most of the time. I’m human and sometimes I can’t help but think “Dang, why can’t that be me?”

We all have similar thoughts. How many times has scrolling through Instagram left you feeling good about yourself? Exactly. While everyone shares their perfect polished life you can’t help but feel a twinge of envy.

I want that too,” you think to yourself.

I took myself more seriously when I deleted Instagram from my phone. That was only the beginning.

I started waking up early to do my best work before envy had a chance to set in. I tuned out the successes of those I admired because, while I’m happy for them, I need to focus on my successes.

No pep talk will ever cure you of envy. Only real actionable steps.

What is the main source of your envy? How can you disconnect yourself from it?

Do it. Focus only on you now.

Think in longer chunks

We live day-to-day but we work year-to-year.

The long-run is a slow growth over many years. If you need a reminder, take out your phone and pull up your camera roll. Look at the most recent pictures. Nothing looks different, right?

Now scroll to pictures from one year ago. Now two years ago. How far back do you scroll before thinking, “Geez, I used to look like that?”
Geez, I used to look like that?

For me, it’s three years. Three years ago I hardly had a freelancing business. I didn’t know what I was doing.

If I go back five years, I see a twenty-something-year-old sitting in a cubicle looking for a way to vent his frustrations. So he signs up for a little writing website with a capital ‘M’ and begins a whole new journey.

Doing this mental exercise is a nice reminder that things will change. Will they be better? I can’t guarantee that. But they will be different.

To make the long-run more manageable, start thinking in months and years. Stop worrying about tomorrow.

Measure progress, but don’t dwell on it

As I’m writing this, one of my recent articles is popping. I keep fighting the temptation to refresh my stats page and see the little green bar tick higher and higher.

I acknowledge the success, it feels good. But it’s fleeting. That’s why I’m back at my desk writing this article instead.

I have an industrial engineering background which means everything that can be measured get’s measured. I track my fitness progress. I track how often I learn a new language. I track the books I read.

In high school, I even tracked how many consecutive days of school I attended (my longest streak was 989 consecutive days).

If you have a specific area of your life you want to improve, measure it. However, don’t dwell on the progress for too long. And don’t confuse periodic wins as a new trend. Success today doesn’t guarantee success tomorrow. You still need to stick to your process.

Sticking it out over the long-run means not refreshing the stats every hour. Instead, prioritize your work above all else and occasionally check to make sure you’re on course.

Find external motivations

All I wanted was to post a thirst trap.

Rippling abs. Swollen biceps. The Italian coastline.

When my aunt announced she picked a date for her destination wedding in Italy — June 2020 — the idea of looking good in a bathing suit crossed my mind.

I have 15 months to prepare,” I thought. So I dropped to the floor and did some push-ups.

I’ve stuck to a workout routine for over a year, I have a 400-day Italian streak on Duolingo, and I have plenty of cash sitting in a savings account to fund the entire trip. This trip was my carrot dangling at the end of a stick. It was my external motivation to keep going.

As you might have assumed, the trip was canceled. The church in Soriano, the one my aunt booked for the wedding, couldn’t accommodate celebrations for the foreseeable future, too many funerals to handle they said.

Nevertheless, this past year taught me how important external motivators are. I couldn’t have done all of those things without the image of a swoll Declan on the Italian coastline.

What are your external motivators? What can you visualize to help you push forward?

Have a plan for the windfalls

Over the long-run, you will have windfalls. These are the unexpected successes. When these happen you need a plan.

Without a plan, you’ll either frivolously spend it away. Or worse, expect the windfall to be a trend and think your standard of living has changed.

To protect myself from these temptations, I stick to a very simple formula for windfalls: 70–20–10.

70% of your windfall goes to your most pressing long-term financial need. Paying down debt. Building up your emergency fund. Retirement. The boring stuff.

20% is for you. Have fun. Treat yo self.

10% is to be tucked away. Put it in short term savings for another day.

I follow this rule because the majority of an unexpected windfall takes care of the things that lead to a secure and steady financial future.

However, I leave just enough to enjoy myself (last year I took my wife to see Hamilton after a small windfall).

You will have wins over the long-run. But don’t let them derail you.

Where to go from here

I’m reminded of a Stephen Pressfield quote:

“The professional has learned that success, like happiness, comes as a by-product of work. The professional concentrates on the work and allows rewards to come or not come, whatever they like.”
Steven Pressfield, The War of Art

Sticking it out over the long-run ultimately means allowing the work to be the reward. Of course, this doesn’t help when bills need to be paid and kids need to be fed. That’s why you stick to your 9-to-5 in the meantime.

Are there times you should quit? Absolutely. But be honest with yourself, do you want to quit because you’re bored? If so, you’ll never cut it out in the long-run.

Be the woodpecker who sticks to one tree. It’ll be worth it.

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Stay-at-home dad. 9-to-5 escapee. Aldi aficionado.

Baltimore, MD

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