I Quit My Corporate Job & It Didn’t Ruin My Life — You Can Too

Note: Post title has been changed from: “How I Quit & You Can Too”

After reading multiple posts lately about how quitting went wrong, I changed the title. It’s went wrong for me before too. I don’t think it’s ever easy. But, this time, I’m on to something. Here’s a look into what I did…

Quitting a full-time job is a hot topic these days. People ask: “How did you do it?” and “Did you have a plan?” I did it in a short amount of time, but I was pretty calculated. I did have a plan. Actually, I had a dream that quickly turned into a plan.

Here’s an unfiltered view into how I quit and the advice I have for others who are looking to do the same. I’ve learned a lot about managing the fears and excitement that come along with the first year of being “jobless” and running a business.

Picturing the day of freedom

When I started planning my big day, I spent a lot of time picturing what it would look like. Like how little girls dream of their wedding day, I’d been dreaming of this big day. What would I wear? Would my boss be upset? Would I be escorted out of the office? What would that day, the day I’d finally choose myself after six years of experimenting with my career, be like? That sacred day of freedom.

Towards the end, I thought a lot about that guy on YouTube. The one who loses it and starts throwing things around the office. I’d never actually do that, but it didn’t seem too far off from how I felt inside. Of course that’s not how I was going to let this go down.

My more realistic mind would draft the email I’d send to my colleagues, carefully crafting the monologue I’d deliver to certain people— especially the ones who wouldn’t be too sad about my departure. I even wrote a few blog posts “announcing” my freedom to the world.

So, what did it actually look like?

Not nearly as satisfying as I imaged. And, I almost guarantee that the satisfaction you’re going to get from telling the world will be short lived too. I’m not saying that it’s not going to be one of the most exhilarating moments of your life, but this is a time to manage your expectations. Your news will be big news for ten minutes and then something else will happen. Whether you’re the founding employee at a startup or one of thousands at a corporation—the business, your boss, the CEO, your team—they’ll all get over it much quicker than you imagined. They’ll replace you, as they should—maybe even with someone better. So, don’t let a grand view of the big day be your focus.

If reaction is the outcome you’re looking for, you need to ask yourself: “Am I really ready?”

Ready or not?

I’m amazed by people who know exactly what they want from childhood. I didn’t realize that I had a burning desire to work for myself until I helped build GOSO, a startup I joined after college, which lead me to turn down my once dream job at Edelman. I wouldn’t know that working remotely and having autonomy was a key driver of my loyalty to a company until I moved for a corporate job. And, I never would have found a passion for building company cultures if I hadn’t taken six years to experiment with my own career in tons of different work environments.

Experience isn’t a certain number of years or jobs, but you need it. It’ll help you create a bulletproof vest for the opinions that are sure to come your way. A year in a traditional office was enough for me to brush off any opinion anyone had about leaving my 9-5. Being in the presence of top executives every day gave me the opportunity to observe. I had the opportunity to ask myself, what if I were sitting in that chair? Would I be happy? Time and time again the answer was a resounding no. I knew deep down in my soul that I wanted something different for my future self. Those truths are priceless during the transition and through all of the hard work that comes with starting a business.

The combination of that experience and planning helped me overcome outside projections of fear others so willing shared.

Planning will set you free

My journey to set myself free had to include planning— money, scalability and sustainability. There’s a Kayne West quote that encompasses my philosophy about money.

“Having money isn’t everything, not having it is.” –Kanye West

I don’t know about you, but I’ve been poor—a couple of times. I’ve stolen frozen burritos from a company I freelanced for (sorry Family Records). I’ve walked way too many miles in the rain because I couldn’t find enough change to put money on my metro card. As far as I’m concerned, it’s all part of the experience. It builds character. But it’s not sustainable. You can’t focus on passion if you’re wondering where your next meal will come from.

There are three things you can do to planning accordingly.

The first, and most obvious, is to meet a savings goal. Get yourself to a place where you won’t be desperate, but you’re not comfortable either. For me, a savings goal of 3-4 months of life with no incoming revenue worked. I wasn’t creating a five-year plan, I wanted out. I’m guessing you do too. So, don’t set a goal you can’t reach in a year. If you do, it just becomes an excuse for not following through.

The second is to set a recurring revenue goal and focus on distributing your risk— now. Start working on your recurring revenue goal— now. If you want to make $8K a month, start working on getting business. Today.

Too busy to do that? Well, the third thing you need to do is change your mindset. Start thinking of your full-time job as a client. Get an assistant. Become a better delegator.

This overwhelming amount of work you have juggling your job and business will force you to create invaluable systems. Systems will save you. They’ll save you time, energy and they’ll save your health. Anytime I do something more than once, I ask myself how I can create system and automate the work. Your time, now more than ever, is money.

Treat time like gold

A system that’s vital for me is one that helps me process and prioritize opportunities. Especially as you’re transitioning out of a full-time gig and taking on a number of clients or projects, you’re going to have to say no. Just as important, you need to fully commit to those things you really care about.

“If you believe that you must keep your promises, over deliver and treat every commitment as though it’s an opportunity for a transformation, the only way you can do this is to turn down most opportunities. No I can’t meet with you, no I can’t sell it to you at this price, no I can’t do this job justice, no I can’t come to your party, no I can’t help you. I’m sorry, but no, I can’t. Not if I want to do the very things that people value my work for. No is the foundation that we can build our yes on.” — Seth Godin

I appreciate the opportunity in many things, and I have a hard time saying no. What’s got me there over the last few months is the not so subtle realization that great work cannot happen when I have one foot in the door and the other out.

I love Arianna Huffington’s saying: “Life is a dance between making it happen and letting it happen. I do my 10% 100%.”

10% —that’s what we have to work with, the rest is up to fate. There’s no choice but to choose wisely.

I needed a system to visualize what opportunities I say yes and no to. So, I created a Google spreadsheet to process clients, projects and work relationships. At the top of the spreadsheet I have short-term goals, 90-day goals and the big picture. Under those goals, I have four columns labeled in this order: In, Needs Processed, Out, and In the Hands of the 90%. I process anything that’s taking a significant amount of time, energy or brain space. I use it constantly, and I suggest it to the people I’m working with too (managers, this is great for employees).

Grab the spreadsheet here and make it your own.

Systems and processes will not only make your business more sustainable and scalable, they’ll help you prioritize your energy and health. If you don’t feel good, you can’t do great work. Period.

Now your plan is unfolding: you’ve set up a savings goal and you’re working on getting one or two additional revenue streams. You have a process in place to evaluate what you’re giving your energy to and why, so you’re well equipped to pick the right clients and projects. Those three elements will help you make sure you don’t get trapped in something that doesn’t fit. You already know what it’s like to give yourself to something that isn’t working. Don’t put yourself in the same trap. That’d just be compromising your freedom in a different way.

Ask for what you really want

Not compromising your freedom means getting extremely specific about what you want. Your own business can quickly turn into the same box that your job was. That’s why you have to master the art of asking for what you really want.

Write down what you want.

Cross it out.

Write down what you really want.

I quit my job in one breath and asked my boss if the company would like to become a client of my new consultancy in the next. With shaking hands, I slid a proposal across the table. To my surprise, a week later, the company signed that proposal and became one of my clients. Many of my coworkers asked, “how’d you get that deal?”

Simple.

I asked.

Recognize upper limiting, guilt and impostor syndrome

When people ask questions like, “how’d you get that deal?” And when things are going well, you might upper limit. I know I do. While I’m working harder than ever, there’s also a sense of ease in my work that’s never been there before. I make my own decisions and manage my own time. I get to travel, workout during the day and keep email off until 10am (sometimes). Those things feel like indulgences. You have to recognize that we feel this way because it’s the way society has brainwashed us. When we enjoy work, it’s easy to feel guilty. We’ve been taught to count down days until retirement, not live our lives happily doing work that sets us free.

Many successful people also battle with impostor syndrome.

“The impostor syndrome is a psychological phenomenon in which people are unable to internalize their accomplishments. Despite external evidence of their competence, those with the syndrome remain convinced that they are frauds and do not deserve the success they have achieved. Proof of success is dismissed as luck, timing, or as a result of deceiving others into thinking they are more intelligent and competent than they believe themselves to be.”

Emotionally dealing with getting what you want. What a silly problem, right? My grand advice? Recognize that this happens. Work to overcome it by having the courage to be happy.

I’ll repeat that:

Have the courage to be happy.

Trust me, it’s harder than it sounds.

Above all else: Remember, you’re going to fail, but you’re not going to die

One of the most important things I’ve learned is that making peace with what you really want also means making peace with failure. I win a little every day, but I fail even more. But, even in my most epic fails, being poor in New York being one of them, I didn’t die.

Write down your worst-case scenario.

Here’s mine: I lose everything I have. I have no money to pay rent. I have to move into my parent’s basement and look for a job. I’m embarrassed because after all of this work, after really putting myself out there, I’ve failed.

Sounds crappy, right? I really hope that doesn’t happen. But, even if it did, I won’t die.

The real worst-case scenario? That would be living my life without trying my hand at setting myself free and doing what I love. That would be the most epic failure, which makes any other failure, including living in my parent’s basement, worth the risk.

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Need more encouragement before putting your plan in place? I love James Altucher’s 10 reasons to quit your job in 2014.