Pursuing Dreamland (or, How to Quit Your Job, Even When You Don’t Know What You’re Doing

When I was a teacher, I was frequently asked the same questions over and over.

The result was that common questions would be answered on posters I had created around the room (like an analog FAQ page).

This strategy allowed me to just stare at kids and point to the posters when they began to repeat themselves.

Probably not the warmest response, but imagine my pain. You can only tell kids what a thesis statement is so many times before you begin to feel a boiling rage. 

In the FAQ spirit, I’m going to attempt to answer the one question that seems to keep coming up in emails and discussions lately:

“How did you transition out of teaching?”

Before I begin, though, I want to point out a realization I had as I was writing this. This story isn’t about me. It’s about the amazing people who have risen up in my life to move me along a path.

I heard Pharrell Williams, in an interview with Oprah, cite all the amazing people in his life who “conspired” to get him where he is today. He references a wonderful book called The Alchemist, which is a story about achieving your destiny through the seemingly random interactions with others along your way.

As I wrote my own story, I couldn’t help but feel what Pharrell was talking about.

Fair warning: it is a little long. I've skipped some details in an effort to bring you key points. I know others have found a lot of value in this journey. I hope you do too.

Here’s goes…

June 2012

At the start of my 7th year of teaching, I take a job at a charter school down the street from my house. We are having a baby and I want to trade in my 45-minute commute (each way) to be closer to my growing family.

I am already thinking about leaving teaching at this point.

Previous to the job offer, I sought out a very particular type of school knowing this move was going to prove one of two things to me:

1) Teaching was perfect for me and I needed to stay forever.

2) Teaching was crushing my soul and I needed to move on.

Since you’re reading this, you know where I landed.

September 2012

School starts in August. By late September, I am ready to quit.

I have no idea what to do. I just want out. I feel stuck. And desperate. (Neither of these qualities make you attractive to employers.)

April 2013

Things have improved, but the die is cast. I am ready to leave.

I have no direction, but I put together a very bland resume, sign up for some job board profiles, and “put it into the universe.”

Turns out the universe looks more like a black hole. This black hole goes by names like Indeed.com and Monster.com.

A word of warning: Stay away from online job boards. I’d go into detail, but that would take too long.

Just believe me when I say, if you’re feeling like your current job is crushing your soul, wait until you send resumes into the void with no response…EVER.

May 2013

My wife advises me to create my dream work environment. She tells me to write it all down; every detail. I think it’s stupid, but I do it anyway (resistance much?). It provides amazing clarity and helps me focus on jobs I actually want.

Personal bonus: I realize my wife is amazing in ways I never knew. This is just one of many times this happens during this process.

Summer 2013

I begin to target sales positions within tech startups. This actually proves to be fairly fruitful.

In one interview, I have a Will Ferrell from Old School moment and temporarily black out as I describe how I “sell” novels to kids everyday who don’t want to read them.

Fairly confident I’ll get the position, I receive a phone call a few days later telling me they hired someone with more experience.

Dejected, I begin to prepare for the new school year that is now just a few weeks away.

I promise to quit by October. Then November. Then over Christmas break.

November 2013

While having our family photos taken for our annual Christmas card, our photographer (an old friend) asks if I’ve found a job yet.

Surprised when I tell her ‘no,’ she asks how that’s possible, informing me of how smart and talented I am. I agree.

She tells me she’s a senior partner at a small, boutique creative agency and invites me to come speak with them about some work.

Not quite understanding how she hadn’t shared this information with me at any point in our five-year friendship, I quickly push this fact aside, and ask, “What kind of work?”

She mentions something about hiring good people, reliability, and copywriting.

I have no idea what she’s saying, but we set up a time for me to come in.

December 2014

My friend and her agency partner throw me a copywriting job.

I have no idea what I’m doing or what the hell a copywriter is, but I keep telling myself to “fake it till I make it.” Whatever the hell that means.

In the meantime, I’m Googling copywriting and reading everything I can find. Most of it is contradictory, and ultimately, confusing.

I continue to do the best I can.

April 2014

After receiving news, following my trial period at the agency, that I will not be brought on full time due to some circumstances beyond my control, I decide to start a business. This brings me to an entertaining side story. Beware: We’re entering a story within a story - Inception-style - so stay with me…

We’re on our way to some friends’ house for a Friday night barbecue. The kids are in the back seat. The phone rings. I answer, get the news. I hang up.

We pull up to our friends’ house. My wife says, “What did they say?”

I tell her they’re not bringing me on. She says, “What are we going to do?”

I say, “I don’t know. I think I’ll start a business.”

She says, “Okay.” (Told you she was amazing).

We take the kids out of the car and never speak another word about it until the next day.

Late April 2014

I receive interest from my first potential client through a freelancing website (not a blackhole job board, mind you).

I’m texting her back and making a deal while I’m trying to teach a class. Note: this is not advisable. Bosses tend to frown on things like this. Fortunately, I didn’t get caught.

We meet. We like each other. (In the back of my head I’m saying: fake it, fake it, fake it…)

She asks me my hourly rate. I tell her. Proud of my feigned confidence in my rate, I’m thinking, “I just doubled what I made hourly as a teacher.”

As we leave, she tells me my rate is too low.

Bewildered, I stare at her. She tells me when I send my proposal, to increase my rate by ten more dollars per hour.

Having my faith in humanity restored, and feeling like I just won the client lottery, I get in my car and try not to scream in delight while she’s still within hearing distance.

The following week, I quit teaching.

Summer 2014

I collect a pay check through the end of June. While it feels good to know there’s money still coming in, I’m also itching for the moment I can be on my own.

July 1st is the first day with no safety net.

I silently panic.

I begin work for my first client, rewriting a website and creating a company newsletter. I’m also still doing a small amount of work for the agency that got me started.

I send an email to every person in my address book, telling him or her that I’ve launched a copywriting business (still un-named). Most of them are as confused by what a copywriter is as I was. I do my best to explain, but most just smile and nod.

I put together a rudimentary website, order business cards, and pick up a few small jobs from friends to build a portfolio. At least I'm savvy enough to know I need to look professional.

Fall 2014

I go about the business of building a business. I have no idea what I’m doing, so I try everything under the sun.

A few things I learned:

  • Hiring an accountant and financial planner is 1) scary; 2) freeing; 3) one of the best things I’ve ever done.

  • “Networking” simply means having a personality and talking to people.

  • Apparently actually doing what you say you’re going to do is amazing to people. Who knew?

  • Confidence looks different when you’re trying to feed your family with your personal work.

  • The State of Colorado apparently runs a deal on setting up an LLC. I lucked into creating a company for $1. Seriously.

  • Naming a business is like naming your child. Everyone has an opinion and they like to share it. Pro tip: Just pick a name and shut up about it.

  • Cold calling sucks

  • Ask lots of questions. It’s the only way to learn.

  • Making mistakes isn’t as bad as it seems. There’s nothing that can’t be undone.

  • Everyone goes on vacation in August and December. These are bad months to build a business.

Spring 2015

So here we are.

I’ve made as much money in the first two months of 2015 as I did in the entire first six months of my business. We're not ready to move to that hut in the Maldives yet, but we're getting there. 

I’ve been thinking a lot about how this happened. I’m not sure I have a “system” for all of it, but nothing beats an unwavering willingness to try new things.

I’m still not sure I know what I’m doing, but I’m starting to figure out that it doesn’t really matter. No one else does either.

And once you can realize that – that we all are doing the best we can – you can start to lighten up on yourself a little bit.

And that feels good.

Is there a big takeaway here? Maybe. The best I can offer up is this: Have faith.

“Faith” isn’t really in my personal lexicon. Maybe there’s room for that old foxhole aphorism here. I’m not sure.

But I do know it certainly feels like a lot of people “conspired” to get me here. I can’t help but return to the idea of living a personal legend.

Despite the title of this post, I would like to point out that blindly quitting your job is not what I'm recommending. You'll notice that my process took about 2 years. I planned. I researched. I prepared. I made the decision that felt right for me and my family. Your journey will be yours. But keep in mind...

When you’re doing something that burns deep in your gut everyday, you can’t help but be driven forward. [Tweet This]

So what are you waiting for?