Do You Feel Trapped?

Discover Freedom—Go as You Please

About five years ago, on a Friday morning, I met my friend and builder Chet Scott at a local Panera.

“Why are you so happy?” I asked. Chet’s glowing smile needed an explanation.

“Oh, nothing much,” he replied with sincerity. “I guess I’m just content.”

Content? Now there’s a word you don’t hear much, I thought.

“Tell me, Chet, why are you so content?” I joked back—sort of. Truth is, at that point in my life I secretly wanted to know his secret.

“Well . . . I guess I’m just at a place in life where I don’t have to be anywhere I don’t want to be,” he stated.

I let his words sink in for ten seconds, then blurted out, “What planet are you living on? What do you mean you don’t have to be anywhere?”

Despite my tone, I knew exactly what he meant. Chet spoke authentically of a freedom few people ever find. Six years prior, he’d left his day job and entered his dream job. Since then he had created a life of freedom. He only worked with his “ideal” clients and he had the bandwidth to read, write, and exercise.

His life seemed . . . light. Not easy, but light.

Me, on the other hand? I lived on a different planet. Maybe even in a different solar system. Before I made my dream job switch, a large portion of my life seemed like one big HAVE TO.

Our weekly “marathon meetings” were the worst. My coworkers and I spent nearly our whole day in one epically bad meeting. Ever hear of Patrick Lencioni’s book Death by Meeting? His subtitle captures the conundrum: A Leadership Fable about Solving the Most Painful Problem in Business.

But unfortunately, at my workplace our weekly experience wasn’t a fable. Come to think of it, Patrick must have placed hidden cameras in our offices to get inspiration for his book.

Maybe you’ve experienced these epically bad meetings at your day job too. Here are a few descriptors that might jog your memory.

Ten Components of Epically Bad Day Job Meetings

  1. Unclear Edges—Waltz in or out when you want; we’ll be here.
  2. Leaderless—Only a ship needs a captain. Meetings are led by consensus.
  3. No Agenda—Who needs one? This would require advance thinking.
  4. Amnesia—Didn’t we talk about that last meeting? No notes = no memory.
  5. Disengagement—Distraction helps ease the chronic pain.
  6. Side Conversations—You’re more interesting than the perceived “agenda.”
  7. No Outcome—Let’s meet to relate, not to achieve our vision or mission.
  8. Indecision—Loops should never be closed. Let’s table it until next time.
  9. No Accountability—Nobody assigned? Nobody acts. Nobody to blame!
  10. Foggy Future—Next meeting time and place? Not now, but only after seventeen back-and-forth emails.

Rather than forward progress, day jobs with regular meetings like this are defined by sideways energy and tons of it.

Yet all over the world, people are solving the sideways energy pandemic with one simple strategy—escaping prison by exchanging their day jobs for their dream jobs. As a result, these DJs reclaim the rights over their lives by changing the rules of the game.

These Rules Were Meant to Be Broken

Check out these rules below. Which ones do you want to follow?

Day Job Rules Dream Job Rules
Sit in an office Go where you want
Work 9 to 5 Work when you want
Look busy Be productive
Expect a set pay Set your own pay
Put off retirement Take mini-retirements now
Boss = other people/things You’re the CEO of YOU

Although we’re early in our conversation, I know what you might be thinking even now:

Sounds impossible.

I can’t do that.

How?

If you feel like pushing back, I understand. But just like when you learned how to ride a bike, you need to suspend the judgment of knowing how. Remember back all those years? You reached a point where you had a big enough why.

Maybe you were sick of riding with training wheels.

Maybe you were tired of being made fun of.

Maybe you wanted to be like the older kids.

Regardless of your rationale, your why for riding a bike quickly turned into figuring out how.

Be encouraged. We’ll spend the first part of the book discovering the why. Then the rest of the book we’ll explore the how. I’ll give you The Dream Jobber Plan, the same nine steps I’ve used to help hundreds of people realize their dream jobs.

You might think DJs are superhuman—or at the minimum superstars. But they’re not. They’re just like you and me. DJs heard the same statistics you’ve heard for years. The only difference is they did something about them.

You know the numbers. According to ABC News, Americans:

A closer look reveals that this “overworked-imprisoned” trend started decades prior. Author Juliet Schor, who wrote the bestselling book The Overworked American in 1992, concluded that “in 1990 Americans worked an average of nearly one month more per year than in 1970.”[2]

As the years rolled by, this trend began to slowly and steadily shape expectations of work. Fast-forward to today, and you simply approach your work differently. Day Jobbers choose their work and try to fit their life in the remaining margins. They work to maintain a lifestyle they can’t enjoy because they’re trapped in their work. Other developed countries aren’t much different. By and large we’ve adopted an “either/or” mindset when a “both/and” one exists too. Notice the subtle but significant differences.

The Day Jobber Mindset The Dream Jobber Mindset
EITHER freedom OR finances BOTH freedom AND finances
EITHER flexibility OR security BOTH flexibility AND security
EITHER significance OR success BOTH significance AND success

The mindset you choose is up to you. With the economic collapse of 2008, aka the Great Recession, the Day Jobber mindset seems less appealing and even less realistic.[3] Many people’s promises of financial prosperity crumbled overnight. With it, their fiercely guarded nest eggs cracked unexpectedly.

All over the world, a new class of people is throwing away the Day Jobber mindset. Why spend decades earning enough money to eventually experience a brief season of freedom near the end of your life? Morbid, but true. Why wait until you’re almost dead before you start to live?

DJs work and play. They create and rest. They’ve chosen to integrate their lives. In the words of L. P. Jacks, they’re masters in the art of living.

A master in the art of living draws no sharp distinction between his work and his play; his labor and his leisure; his mind and his body; his education and his recreation. He hardly knows which is which. He simply pursues his vision of excellence through whatever he is doing, and leaves others to determine whether he is working or playing. To himself, he always appears to be doing both.[4]

Imagine your friends and family seriously scratching their heads when they observe you. Not because of your new hairstyle (irrelevant for me as I don’t have hair) but because of the way you work. You have so much fun because you love what you do and work doesn’t seem like work.

Similarly, imagine your coworkers confused because you can’t wait to spend time with your loved ones. You look forward to investing in these relationships because, like you, they’re life-giving.

Freedom is the first benefit of joining the DJs. Because they’ve achieved freedom, they can now go as they please. They’ve exchanged their have tos for want tos and their day jobs for their dream jobs. But this freedom isn’t the only benefit. DJs experience financial freedom too.