8 Steps To Weaning Yourself From The Corporate Teat

(Or: How To Transition Out Of The Corporate World Into Full-Time Freelance)

Are you in a soul crushing yet high paying job and want out but don’t know the next steps? Are you just bored at work and wish there was more to life? Do you have a passion you wish you could turn into a full time job? (If not, you may want to read “How To Find Your Passion” then come back here.) I’ve transitioned from management consulting to working for myself in the arts, without spending time in a homeless shelter. Here’s some lessons I’ve learned along the way that may help you.

Step 1: Bide Your Time…

…a.k.a. “Save Up Money First.” Be strategic about your next moves. You know you want to quit. Should you tell the boss to fuck off tomorrow? No! Bide your time. Figure out your exit strategy whether it’s save up a year’s worth of expenses before quitting, get laid off and collect unemployment or shift to part time, figure out the softest landing. If you quit without financial room to maneuver, you might get cold feet, and even if you do quit, you’ll be more likely to start at another job you dislike sooner than later because the money will get tight.

Even as I joined Accenture, I knew that I wouldn’t want to be there forever. (Although many of the people who I know that have stayed there for 20+ years also felt that way when they started.) My original plan was two years. It turned into three. Knowing that I wasn’t going to be there forever, and that the money wouldn’t be coming in forever, I set up a savings account. In a different bank than my checking account. And I had part of my paycheck auto deposit into the savings account (hat tip to Ramit Sethi’s automating post). And I wouldn’t look at that account for months at a time. (Unless my car needed repairing or something.) This way I was already used to living on 20% less than I was making. After three years of saving like this, I had enough cushion to be able to pay my expenses for over a year, even if I didn’t make a single cent doing other things.

Step 2: Hold On For As Long As You Can Take It…

…but not so long that you lose your guts.

Basically don’t quit until you’re making a partial side income, or at least have a few clients signed up. Do your passion project work on the weekends and evenings for as long as you can. (Or during work hours if you have some downtime and discipline.) Hold off on quitting until you have something resembling clients and a small income. It’s easier to go from making $100 a month freelance to $2,000 a month in freelance than it is to go from $0 to $100. (Not that either part is easy, and all income is gradual improvements in my experience.)

When I quit consulting, I had a smaller income lined up as a grad student. I quickly realized I didn’t want to be there and had saved up enough money that I could just quit without worrying about immediate employment. Before I moved back to NYC, I talked to some comedy places that had already been using me and paying me a few bucks to make sure I’d be welcome back. So when I first went to “full time artist” I had my beer and food expenses covered and was paying rent out of savings. After two years, my monthly income wasn’t high enough that my savings got really low, so I had to take on an additional consulting like gig, but this time I did it as a freelancer. And it had a finite end date after 9 months. I was making more money in comedy at the time, but not enough to cover all expenses. So I built up my savings again in those nine months. After working from 7am to 1am nearly every night for those nine months, I had enough comedy income (and motivation to never go back to an office) that I’ve been surviving ever since.

Step 3: Live Below Your Means Before You Quit

Even when I could afford to live in Manhattan (where it’s $2,000+ for a studio) I choose to live in Astoria ($900-$1100 for a 1br). Then I found a roommate to split costs even more. When you’re freelancing, you’ll have some slower months than others. Knowing that you can at least cover your rent helps you sleep at night. And you’ll need that sleep because all you do is work. This is the most important thing: Finding the cheapest place you can see yourself living in comfortably for five plus years. Because it will probably take you much longer than you expect to get to a similar financial foothold as some of your peers who’ve stayed in the safer waters of a steady paycheck. All other expenses (like going out to eat) you can cut down on quicker during lean months. Rent is the one that will get you the quickest. I wouldn’t advise moving back in with your parents, as it might kill your motivation. Knowing you have to make some money every month will keep you hustling harder.

Step 4: Show Up Every Day

So you’ve finally quit your structured job. Now what? Figure out your daily process. And stick to it. (See Scott Adam’s book and The Jerry Seinfeld Method.) I have a huge board where I have six daily goals: Write, Perform, Exercise, Eat Right, Make Money and Meditate. I put a check mark next to each day when I do that activity, and an X when I don’t. I don’t do all 6 activities each day, but I do most of them, and I’m at least aware of the minimum I should do to have had a “successful day.” I also have a daily to do list, things that I should get done that day. Although it usually takes me 3-4 days to finish it. But it’s right by my computer. So I know what I should be doing. It stares me down when I start dicking around on the internet too much.

Ben’s Daily Board


Have a place where you can interact with like minded individuals daily. For me, this was easy because I’d be at comedy shows every night. If you’re in a different field, perhaps you schedule yourself to attend a different meetup or networking event every night. Or if you can afford it, shared office space. You want to avoid a situation where you have no human contact weeks at a time and where the Chinese food delivery guy is your only source of news from the outside world. This step should really be four steps, as it’s the most important thing when you’re trying to establish yourself. People need to see that you’re serious and always around before they give you a break.

Step 5: Be Open To Niches You Didn’t Originally Consider As A Possible Business

Even if you’re not in a tech startup, think like a tech startup. Twitter wasn’t twitter when it first started, but it noticed its early users were using their system and made changes accordingly. Keep your head on a swivel and notice what’s working, then put more effort into that.

I originally bought a very nice video camera because I wanted to film and review my comedy performances. (I still had my consulting job, so it didn’t hurt that I could spend more money.) I had no other motives for buying it other than my own video review. Soon after getting it, other people started asking if I’d film their performances. This quickly turned into an accidental business and a nice source of side income. By showing up every day and keeping my eyes open, I pretty much created an extra job for myself where none existed before. From this, I also taught myself video editing and how to shoot sketches and short films. People started paying me to do that. Then they realized I was good at computer stuff, so they asked if I could build their websites. Three businesses that I didn’t plan on doing just from being aware of what was going on around me.

Step 6: Create Multiple Income Streams

Until you’re sure that you have enough business coming in from doing only one thing, do a few different services so that it averages out into an income for each month.

Last year I got paid for doing the following things: performing comedy, voice over work, video filming, producing comedy shows, website design, video editing and selling copies of my book. Each month had a different percentage breakdown of which activity brought me the most money. If you work freelance and for yourself, you’re gonna want to have as many income streams as you can until one of your businesses really takes off. Is it a lot of work? Yes. But it’s still better than not controlling my own schedule and working on things I want to work on.

Step 7: Find Mentors

If you’re showing up every day, you’ll be meeting people. Some of them doing what you want to be doing. Some subset of those, you’ll be on the same energy vibe. Try to eventually start working with or for them. Ask for a piece of advice here or there, slowly they’ll become your mentor without even realizing it. Have a few people like this to bounce ideas off of.

Whatever you’re trying to do, someone has done something similar before and succeeded. If you don’t know who that is in your field, have you been showing up every day? I’ve found people are happy to share their experiences and advice when you remind them of a younger version of themselves. Hell, that’s what I’m doing right now.

Step 8: Have Gratitude

You’re gonna be annoyed that you’re not living a baller lifestyle for a bit like some of the people you keep in touch with. They’ll be buying a house or having a kid while you’re giving birth to your projects. Remember that people only post the highlights on Facebook and not their miserable minute to minute daytime existence. Remind yourself that if you don’t have to go to a job you hate, you’ve already won.

Thank you to Ishita Gupta for prodding me to write this post.

Ben’s eBook: How To Find Your Passion

This 25 page book covers my decision to drop out of graduate school to pursue comedy and how you can use the lessons I’ve learned to find your passion before it’s too late.

Click the image above or download the pdf here

If you find this useful, please pass it along to anyone else you think it might help. Comments, as always, are welcome.

If you like my eBook and have a group you think would want to hear me present this message as an hour long talk, book me. The talk is based on the book, but funnier and more interactive, as I’m a stand up comedian after all.

My Op-ed piece in today’s paper

If you read my goals for this year, two goals mentioned a motivational speech and an eBook, which probably didn’t make any sense. Well, my opinion piece in The Stamford Advocate (my hometown paper) should clear things up a little.

I’ve finished writing, and will shortly be releasing an eBook called “How To Find Your Passion.”

For now, here’s the opinion piece.

Link to original story or read the article below:

More passion, not more science education

Published: 04:41 p.m., Thursday, January 21, 2010

By Ben Rosenfeld

Anywhere you look, there is talk about how America is falling behind in science and technology. And a lot of pundits say it’s all the fault of education. “We need more education.” “We need better education.” “We need better schools.” The list goes on and on and on.

We don’t need more education; we need more students to develop a passion for science. We have plenty of universities (and primary schools) that teach science, but they teach it in such a boring manner that only those who already want to become a physicist or mechanical engineer get through the drudgery of those lectures and problem sets.

Most of everyone else studies psychology, communications or economics. We can either make “hard science” classes more interesting, which wouldn’t hurt, or we can make sure that by the time students get to a university, they love science so much that they’re willing to get through those hard classes.

I’m not simply making a theoretical argument: I enrolled in a PhD program in Neuroeconomics at a top five university (Caltech), and five weeks into the first semester, when the workload was a lot more intensive than in undergrad, I realized I didn’t have the passion to continue graduate school. I never enjoyed biology and I tried avoiding math as much as possible because I never found it interesting. I wasn’t scared by the work, but I couldn’t force myself to work so hard for something I didn’t love. While I have the passion for figuring out why people do what they do, I was missing the passion for neuroscience and the passion for math.

My two months at Caltech weren’t all for naught, however. Being there helped me realize my passion is comedy. (I’m still studying human behavior: Instead of asking, “Why do people give money to other people?” I’ve started asking, “What makes people laugh?”)

My passion for comedy has helped me tolerate standing in Times Square in zero degree rain and snow passing out comedy flyers for three hours in order to get seven minutes of stage time. Passing out fliers never fazed me, as I viewed it as part of the process that I need to go through to develop as a comic. On the other hand, I viewed math and biology as part of the process to avoid.

When you love doing something, you run through the walls that stand in the way of achieving in that area. But when you don’t love doing that thing, the walls make you turn around and do something different.

In India, China and Japan, science and technology are keys to a “good job,” so even people without much passion for it will throw themselves into it. In America, science and technology aren’t the only (or the best, or easiest) ways for striking it rich (see: Banker, Investment), so you actually have to like science to study it. (This is also why there are so many undergraduate economics majors in this country who hate economics.)

So how do we get someone to be more passionate about science? I’m not sure. Maybe it’s genetic. Maybe it’s determined before a child enters kindergarten. But I have a feeling this isn’t true. I had zero interest in philosophy until I took a philosophy class my senior year of high school. After that class I liked it enough to major in philosophy.

Interest is the reason a seven-year-old can figure out a baseball player’s batting average but doesn’t know how to divide regular numbers. If a teacher makes a subject more interesting, there’s a higher likelihood that a student will start to develop a passion for that subject. We don’t need more education, we need more teachers who know how to make students passionate about science and technology.

Ben Rosenfeld is a New York City comedian and author of the forthcoming e-book “How To Find Your Passion.” Before becoming a Caltech PhD dropout, Ben graduated from Stamford High School in 2002. His e-mail address is ben@bigbencomedy.com.

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