In case you missed it...

Since I'm an infrequent public speaker and I was relatively terrified of drawing a total blank when it came time for my presentation, I basically wrote a version of my talk before last Wednesday's event. Some of my friends were unable to attend, and others mentioned they would have liked to have been there, so I figured I'd go ahead and fill in the holes and post it here. Enjoy!

Refresh Richmond // 804RVA Meetup // Wednesday, 05.14.2014

Quit your job: And other sage advice from a reformed workaholic

So here’s a little known fact about me: exactly one month ago I quit my job. I hadn’t even given it that much thought at the time. I woke up one morning and knew it was time. I had mentally rehearsed my approach, but got derailed by one last hilariously appropriate 'sign', and that was that. Oh well. It really was a great speech…

On the drive home, I started to think about how annoying it was going to be to go through the whole story… I could already see the concerned expressions and hear the “what are you going to do next”s when really, in less than 15 minutes time I had gone from the most frustrated I’d been in years to the happiest I’d been in years. So I figured I’d write it all out, put it into a blog post, and a week later, I launched my new brand with this story.

A few days later I got an email saying that my name had come up as a suggestion for this event, asking if I would I be interested. I guess I assumed I’d be talking about branding, or freelancing, or starting your own business, because it wasn’t until Candace and I talked on the phone that I realized they were actually interested because of my post. She said it "resonated with people." I checked my analytics that night and holy shit, people really hate their jobs!

So here it goes.

Step one: Quit your job.

I had dinner on Saturday night with my college roommate who also went through a big career change a year ago, and she was asking me about my upcoming presentation. She said “You can't just stand in front of a room and tell a bunch of people to go quit their jobs. Not everyone has that option. Most people can’t work without a job… So what are you going to talk about.”

Good points. I guess I’ll start there.

  1. You can't just stand in front of a room and tell a bunch of people to go quit their jobs. Sure I can. I just did.
  2. Not everyone has that option. Sure we do. We all have the option to do what we want to do with our careers. Let’s talk about how to make that decision and whether or not it’s the right decision for you.
  3. Most people can’t work without a job. I’m willing to bet that anyone can create their own job if they really wanted to. The question is, is it the right thing for you? Maybe, maybe not. All I know is how I figured out what was right for me.

Can you quit?

Sit back, and take a few seconds to think about your dream job. How many of you are doing that job? How many of you do that job in your free time after you’ve finally finished doing your real job?

There will be no right time

Within minutes after I shared that blog post, I got an email from another friend who said that she has been toying with doing the same thing, and asked how I knew it was the right time?

If you wait until you’ve saved enough money, landed the perfect client, covered your salary, whatever it may be, you’ll never do it. If you’re doing freelance work on top of a full time job, where is that money going now? Set it aside and pretend it’s not there until you really need it.

Have a bug-out career

I quickly lost trust in my last situation. Too much money was being tossed around, too many promises were being made … I hoarded everything. Just because you earn more money doesn’t mean you have to spend more money.

Years ago I also started designing posters and selling them on the side. Instead of spending that money I decided to reinvest all of my profits back into the company so that I could continue to create more products and not have to worry about how I was going to fund them. I knew that this side business made me happy, and it was work I enjoyed, so I’d found a way to support it and grow it organically.

Train yourself to save money or invest in your own business ideas so you have options available when you decide the time is right.

I decided I was quitting at 4am on April 15th. Had I thought about it before then, perhaps, but did I have to mull it over? Not one bit. I’d set myself up with options that would be there in 2024, or on April 16th when I needed them.

Should you quit?

Back to that survey. I setup a questionnaire at my last company so that people could get to know each other better, and the dream job question was on the list. Of 21 employees, only 1 person answered with something that was remotely close to what they were actually doing.

The most telling thing was the fact that I had never really thought about my own answer. What was my dream job? I want to sell and design paper products. It’s what I’ve done in my free time since the 7th grade. But I can’t actually make that my career.

The problem is in our blood

In high school I graduated at the top of my class. I played basketball, and as a nerd I was recruited by all 8 Ivy League Schools. Since I wanted to go into business, I chose Penn. I did all of these things, because it was the way things should work. If you’re successful at basketball, you play in college. If you’re smart, you go to a good school.

I didn’t actually stop and ask myself if I liked what I was doing until I was faced with a career-ending injury that forced me to take a semester off. I realized, I had no desire to go back whatsoever. I hated it there. I had grown to hate basketball. I was successful, but miserable because it wasn’t the intended path for me.

Think about what the path should look like, not what it’s supposed to look like

I left an ad agency at 26 to start my own company, which was my first attempt at freelancing. It was awesome. I made more money, I traveled all the time, I met new people, and I loved the work I was doing.

The more successful I got, the busier I got, and the more I needed help so I brought on a partner. And soon we needed more help. This was how it was supposed to work. Successful design agencies get bigger, and they get bigger clients, and they have bigger budgets, and that’s how they grow.  But with that, I spent less and less time actually getting to design anything, more time managing other people, more time working on RFPs, more time behind my desk, and more time stuck to a schedule.

For some people, this transition is ok, because the goal of growing a larger team, and being a bigger agency outweighs the negatives. But I’m a designer. Can I manage people? Sure. But what would I rather be doing? Designing things.

The other problem is I do my best work when I’m alone. It’s kind of hard to run an agency when you just want to be left alone all the time. It wasn’t fair to a partner or to employees to constantly be waiting for them to go home for the day so I could finally get to work. It also wasn't fair to me to put off my own life in order to compensate for all the extra time I felt I had to commit to the business in order to accommodate this quirk.

It took me a long time to realize I’d created another college basketball scenario out of my career. I needed this last transition—my final career-ending injury—to make me step back and think about where I was and how I had gotten there.

You need to be honest with yourself and really think about what it is that makes you happy. That’s right. happy. Try to think about happiness as the equivalent of success and see if any of your decisions change. Maybe I’ll start working on those paper products a little more seriously.

Experts agree, I’m no expert.

Obviously I’m an expert at absolutely nothing, so please, make use of that. (Opening up for Q & A.)

My parting words are, if you’re on the fence, go for it. If you are unhappy, do something about it. And if there’s something you really love to do, find a way to spend more time doing it.

As my designcrush, Jessica Hische, has said best: 

“The work you do while you procrastinate is probably the work you should be doing for the rest of your life.”