3 years ago today I left my corporate job at Procter & Gamble to focus on Humor That Works full-time. In those 1,095 days, I’ve had some incredible adventures and met some amazing people.
In honor of my anniversary, I thought I’d answer some of the most frequent questions I get about leaving the safety and security of gainful employment at a company.
How did you know what you wanted to do?
I wish I had a “sexy” answer where I said it all happened in one single moment of hilarious clarity… but that’s not how it went down. It was a gradual progression of events and experiences that led me to teaching people about the value of humor.
When I moved to NYC with P&G in 2008, I had a strong suspicion that I wasn’t a lifer–that at some point I would decide to leave. But I wasn’t 100% sure of what I would do. I was performing a lot of stand-up and improv comedy at the time and thought I might want to do something in entertainment.
In my experience, the only way I can know if I want to do something is to actually try it, so I experimented with a bunch of things part-time while still at P&G:*
- I toured for a bit as a stand-up comedian. I didn’t like being in a different hotel every weekend with people I didn’t know where the most common form of passing the time was drinking in bars.
- I wrote for a sketch TV show on Dish Network. I didn’t like giving over creative control of an idea I had and seeing it poorly executed.
- I co-wrote and edited a short-film. I had a lot of fun on the project but realized I didn’t want to spend every day behind a computer meticulously shaving off milliseconds to get a shot to look right.
- I acted in a few sketches and took an auditioning class. I didn’t like the process of auditioning and realized I wasn’t very good at “acting” (making memorized lines look spontaneous was hard).
- I taught people about the value of humor and used improv exercises in some of my trainings. I loved this. It was like performing stand-up and improv comedy but with the added benefit of getting to tell people what to do.
Ultimately it was the humor work that I enjoyed the most, so I pursued it further.
How did you get started in talking about humor?
Again, no sexy story, just a lot of work and some reflective thinking.
The short answer looks like: Engineer -> Improv -> Project Manager -> Effective with People -> Stand-Up -> Blog -> Corporate Humorist -> Humor That Works.
This timeline covers the span of 3 to 28 years depending on how you look at it:
- Engineer: I’ve always been an engineer and have been obsessed with efficiency. I went to The Ohio State University to get a degree in Computer Science & Engineering.
- Improv: In college, my best friend wanted to start an improv comedy group and needed people, so he forced me to join.
- Project Manager: After graduating, I started working as a Project Manager at Procter & Gamble, first in Cincinnati and then in New York.
- Effective with People: While at P&G, I realized that you can’t be efficient with people, but instead you have to be effective. While that wasn’t covered in my CSE degree, I did learn the skills from improvisation.
- Stand-Up: At the same time, I was performing stand-up comedy in Cincinnati and inviting P&Gers to my show. I was mostly talking about nerdy things like math.
- Blog: My first year at P&G, I started writing an internal blog called Life of a New Hire, where I wrote about my experiences of a being a new employee at a big company. After a year, I figured I was technically no longer a New Hire, so I decided to start a new blog.
- Corporate Humorist: Because of the stand-up I had been doing, a few different P&Gers had been asking me about humor. I decided my new blog would be about humor and proclaimed myself the Corporate Humorist of P&G. I also started offering up humor “services” to organizations within P&G, e.g. giving presentations on humor, leading teambuilding activities, and hosting events.
- Humor That Works: From the internal blog I found I really enjoyed talking about humor and people were interested in what I had to say. I figured if people at P&G enjoyed it, the rest of the world might as well. So I started Humor That Works as a public version of what I was doing at P&G.
Why did you decide to leave?
I loved my job at P&G. I was working on challenging projects, worked with incredible people, and was consistently adding bad puns to the ends of my email.
But the more I worked on humor, the more I fell in love with it. The joy from P&G stayed the same while joy from humor increased, leading to a much larger delta between the two, as illustrated by this graph:
Was it scary leaving your corporate job?
Honestly? No. Dishonestly? Scarier than 1,000 spiders.
No, it wasn’t that scary for me. I’m a Project Manager and pretty risk-adverse, so I did a lot of preparation before making the jump. I started blogging as the Corporate Humorist in 2007 but didn’t leave P&G until 2012.
In that time I tried a bunch of things out: I did speaking events in my free time, I took vacation days to see if I could actually motivate myself to work, I talked to people who were doing what I wanted to do. Basically I tried before I buy-ed.
In the days leading up to the decision, I asked myself two questions that I now use anytime I’m faced with a potentially life-changing choice:
- What’s the worst that could happen? Humans are driven more by punishment-avoidance than they are reward-attainment, so I tried to think about what the “punishment” would be in making a choice and see if I’m OK with that result.
- 30 years from now, which decision will I regret not doing? Very few of my regrets come from having decided to do something, most of them come from not having done something (asking that girl out, trying that food, or riding in that helicopter). So which option would I regret having not done?
Thinking about those two things made it easy. Even if I failed miserably at running my own business, I felt confident I could get another job. With P&G on the resume, improv and humor as a skillset, a network of incredibly smart, talented, and kind people, and a degree in the exploding field of computer science, that seemed a reasonable assessment.
And had I stayed, 30 years from now, I would have always wondered “What could I have I accomplished if I had left?”
So I left not feeling scared but excited.
How did you know it was time to leave?
Right or wrong, I spend much of life quantifying what it is that I do. I tracked my time, 24 hours a day, for an entire year. I know the number of times I’ve performed and the rough estimate of how people have seen me. I can tell you how many times I worked out last year (305).
As a result, numbers motivate me. So I created a list of goals to hit before I’d be comfortable leaving:
- Speak in front of 50+ audiences.
- Make at least $10,000 in a year from speaking engagements.
- Reach 1 million visitors on my website.
- Have at least 10 rock-solid testimonials.
- Spend at least 7 straight days working on just Humor That Works.
Once I had achieved those, I felt ready to go. Then it was a matter of finding the right time for the business.
What did your mom think?
My mom, one of the greatest people in the entire world, was very supportive. She was a bit worried, of course, but she encouraged me to do what would make me happy.
I also told her the sooner I left to start my own business, the sooner I’d build it to the point it could support a family, the sooner I’d settle down, and the sooner she’d have grandchildren. That seemed to help.
What do you miss most about the corporate world?
Ask anyone who has ever left P&G what they miss the most and they’ll say the people. I thought it was such a cliche answer until I left and realize it’s 100% true. P&G hires some incredibly talented people and then helps develop them to become more awesome (you have to at a promote-from-within company).
I miss having great managers who guided me through difficult decisions. I have mentors that certainly help, but now that I run the show of my own company, there’s no one as invested as I am that can give guidance on what to do next.
Also, when employed by someone else, you know that a paycheck is coming unless something drastic happens. In self-employment, no paycheck is coming unless something
Are you happy you left?
I wake up everyday working on something that I’m passionate about that I believe improves the lives of the people I work with. I work with great organizations from all over the world and have traveled to places I didn’t even know existed. My bio says that I’m obsessed with chocolate and event organizers often gift me with a box as a thank you.
I’m definitely happy.