Escaping The Waiting Place
I’ve learned more about life from Dr. Seuss than all the great philosophers combined.
In Oh, The Places You’ll Go!, the hero grinds on for miles toward a most useless place: The Waiting Place.
…for people just waiting.
Waiting for a train to go
Or a bus to come, or a plane to go
Or the mail to come, or the rain to go
Or the phone to ring, or the snow to snow
Or waiting around for a Yes or No
Or waiting for their hair to grow.
Everyone is just waiting.
Waiting for the fish to bite
Or waiting for wind to fly a kite
Or waiting around for Friday night
Or waiting, perhaps, for their Uncle Jake
Or a pot to boil, or a Better Break
Or a string of pearls, or a pair of pants
Or a wig with curls, or Another Chance.
Everyone is just waiting.
When I read those words, I felt a twinge of sadness. Sadness for all the people in the pictures, waiting for this or that. Waiting to live their lives. Waiting because they were scared of acting.
And I realized it’s sad because it’s true.
It isn’t a made-up fairy-tale creation. It’s a mirror held up to reality. To the world we all inhabit. To the lives that pass us by while we’re waiting for the perfect timing. Waiting for the chances that never come.
How many ideas have you had to start a company?
“After I find the right partner,” you told yourself. Then you saw someone else building your idea.
How many times did you want to talk to a girl at a bar?
“After the next drink,” you told yourself. Then she disappeared.
How many dream jobs have you seen posted?
“After I have a little more experience,” you told yourself. Then it was filled by a candidate with less experience than you.
Waiting is the human default. And it isn’t because we’re not ready. It’s because we’re scared of what might happen. It’s easier to wait—to stick with the status quo—than to take a chance, risk rejection, and find our true potential.
I’ve spent plenty of time in The Waiting Place, but I’ve also left it enough to know what the other side feels like. These are a few of my stories. I hope they inspire you to leave your Waiting Place.
A real estate investor
There’s a thin line between preparation and procrastination, and my friend and I had crossed it. We’d been talking about buying an investment property for months—okay, years—and we’d diligently done our homework.
We listened to hundreds of podcasts, read dozens of books and articles, and analyzed countless deals in our target market.
We were waiting until we had enough money. We were waiting until we understood the market. We were waiting until we found the perfect deal.
Waiting, waiting, waiting.
Finally, we decided to act.
We called a realtor, scheduled showings, and hit the road to look at houses. After more than a year of planning, we were finally taking the first real step. We had eight houses on the schedule to see that Saturday, and we agreed to buy one of them before the weekend was over.
That’s exactly what we did.
We saw shanties and shacks. We saw overflowing litter boxes, rooms split by curtains, and dirty mattresses on bedroom floors. And then we saw the winner—the tallest of the seven dwarves.
We jumped. We made an offer. We closed within a month.
We were out of The Waiting Place and into the arena.
Over the next year, my friend and I bought three more properties. We grew from zero apartments to 12 apartments in less than 12 months. We figured out financing, tenant placement, repairs, and management. We dealt with doors being kicked in by police. We solved sewer blockage problems. We navigated lead paint remediation.
And within three years, we sold them all, nearly doubling our initial investment.
The thing about action is it catalyzes more action. Once you buy a house, you’re met with all kinds of other problems to solve. And you have no choice but to solve them. So you take more action, build more confidence, and feel a little more ready to act on the opportunity.
The opposite is true of waiting. The more you wait, the less action you take. The less confidence you build. The more excuses you find to keep waiting. You live a life of safety, but you never accomplish anything.
And I’d argue life’s biggest risk is never taking any risks.
A hopeful entrepreneur
Most of my actions turn out less successful than my real estate investing.
I started a company that never made a dollar. I spent $20k and more than six months building an app, negotiating contracts, working with contractors, recording audio, and executing what I thought was going to be the perfect business plan.
I was building Audible for blogs. It was going to be an overnight success. I was going to sell it to Amazon for a couple million, and tout my success on Rogan and Ferriss.
At least that’s what I thought…
I built a cool product, but it turns out nobody wanted it. Or I wasn’t smart enough to get it in front of the right people.
So it was a failure on paper.
It burned a lot of my money. It ate a lot of my time. But it also taught me that I can build an app. I can manage a project from start to finish. I can negotiate good outcomes with people much smarter than me. I can manage a team of remote employees.
These are lessons I never would’ve learned if I stayed in The Waiting Place. It’s confidence I never would’ve built if I waited for the right time.
Most importantly, I never would’ve learned that great distribution with an imperfect product beats a perfect product with no distribution. This is a lesson I could read in a book, but it’s meaningless without the experience. And it’s a lesson I’ll apply to future ventures.
It’s a lesson I learned from action—a lesson I couldn’t have learned from waiting.
A startup employee
I was tired of my career in consulting. I’d spent eight years billing long hours on projects I hated.
What I did like was writing. Creating. Podcasting. And I kept telling myself, “someday I’ll do more of that.”
But then I had a chance to leave the boring job I didn’t like to join a startup working with podcasters. It was a chance to run the company’s operations, build a growing team, and get in on the ground floor of a startup.
It was a risky decision. It was a huge pay cut. It was at a time when my wife was still in school, so we didn’t have another income.
It would’ve been easy to stay in The Waiting Place.
But I didn’t.
I took action. I quit my high paying job and rolled the dice on the new position—doing the thing I was excited about.
It was great for six months. Until it wasn’t. Until the founder stopped doing his job as a salesman and we ran out of paying clients.
It was great until I got the phone call telling me there wasn’t enough money in the bank to pay my next paycheck.
Taking action is the right path, but it can come with downsides too.
So I left the company. But I don’t regret taking that job. I learned some valuable lessons.
I learned that when joining a startup, you must insist on knowing the company’s financial position. I learned that people who buy their own bullshit are often as good at selling it to you. And I learned that losing a job isn’t that bad of an experience. It’s just a small bump in the road.
Why the risk is worth it
After reading about my experiences, you’re probably thinking, “he loses more than he wins. Maybe it’s better to stay in The Waiting Place.”
That’s a fair opinion to have.
But what I gained every time I left The Waiting Place was experience.
If you’re always waiting and never doing, you don’t learn real-world lessons. You don’t build your portfolio of stories, successes, failures, and experiences. And those are what lead to future wins.
You don’t learn that success can be life changing, and failure usually isn’t. You don’t learn resilience. You don’t learn how to scramble and solve problems when you run out of options.
And maybe most importantly, the people who can open the biggest doors for you care about action.
They don’t always care that you succeeded—although it’s a nice benefit. They do always care that you had the balls to give it a shot. They care that you learned something along the way and adapted in your next experience. They care that you have a story to tell.
So while my swings haven’t always turned into home runs, they’ve benefitted me in other ways. And the successes I have in the future will be a result of the action I’ve taken in the past.
I’m sure of it.
And that’s what Dr. Seuss was talking about on the very next page when he wrote:
NO!
That’s not for you!
Somehow you’ll escape
All that waiting and staying.
You’ll find the bright places
Where Boom Bands are playing.
With banner flip-flapping,
Once more you’ll ride high!
Ready for anything under the sky.
Ready because you’re that kind of a guy!
I escaped The Waiting Place.
I’m heading to the bright places where the Boom Bands are playing.
I’m ready for anything under the sky.
I’m ready because I’m that kind of a guy.
Because I took action.
Because I escaped The Waiting Place.
I hope you can too.
Photo by Liz Guertin on Unsplash
