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It’s the final day of the year and my wife and I have enjoyed spending the past week with family in Arizona. Ahhhh…warmth. It’s been so nice!

We’ll be (reluctantly) heading back to Portland tomorrow. It’s going to be hard leaving 70 degree weather for the rain and cold.

The past few days have been great because I’ve stepped out of my normal routine and slowed down. I’ve been enjoying daily hikes in the desert and eating more than my share of great Mexican food while here in Phoenix.

I’ve also been taking an honest assessment of the past year.

This was a year of highs and lows for me. I started a blog that turned into a weekly podcast. And then I starting coaching people. And in August I got the disturbing news that I was being laid off from my corporate job.

I had an important decision to make. Do I go get another corporate job or do I dive head first into the business that I had started on the side?

I chose the later and so far the journey has been spectacular and I’ve learned so much in such a short period of time.

But today I want to get real with you and tell you exactly how I put myself in a position to choose pursuing my own business full time. It was not a choice that I made lightly. And neither should you.

Pause for a reality check…

Before you take advice from me or anyone else to quit your current job and go “live your dreams,” breathe for a moment and then slap yourself in the face.

After you’re done with your deep breathing and you’ve given yourself a little wake-up slap, ask yourself what will it really be like to quit your job?

More often than not, people simply aren’t prepared to quit their job. Most have no idea what it would be like to suddenly rely on yourself for your income.

I’m going to tell you from personal experience that making a living on your own is way harder than you think it will be. You will work more hours, make less money and be thoroughly confused about what to do next.

The good news is that this phase is temporary. If you have a solid plan and you have the resources (time + money + support) to see it through, it will be one of the most rewarding experiences of your lifetime.

I’ve never done more purposeful and rewarding work than I’m doing right now. I happily work more hours than I worked in my corporate job because I love learning and figuring out new ways to add value.

Averting Disaster

Who wouldn’t want to quit their boring corporate job and do something more meaningful?

Seems like a simple enough question to answer, right?

Well, I’ve got news for you.

Unless you’ve already got plenty of savings stashed away and have simplified your life significantly, quitting your job will most likely be a disastrous move.

For most people it would be extremely stressful to try and create a new business under the conditions of needing to generate immediate income.

There are exceptions of course, but most of us would be better served with a plan that gives us our best shot at succeeding.

The question then becomes, how can I quit my job without quitting?

Quitting your job is a huge decision that can have catastrophic consequences like going broke, being at odds with your family, and losing that corporate reputation that you’ve spent years creating.

Quitting a job without test-driving entrepreneurship is kinda like:

  • Marrying someone you’ve only met online…once!
  • Deciding to run a marathon next week with no training. Ouch!
  • Moving to a new city without ever having been there. Hello neighbors!

Could it work out? Sure! But the the chances of something really unpleasant happening are very high.

The first time I considered quitting my corporate job was right after attending an inspirational event for creative entrepreneurs in the summer of 2010. This event filled me with hope and unlocked new possibilities that had been dormant for what felt like a very long time.

But a week after the event, I felt alone and unprepared. Most of my friends and family members were in a very structured work environment. I was in this confusing place of wanting to quit my job but not having a clue how I was going to pull it off.

Quitting my job was the equivalent of putting all my chips on a bet where I didn’t know the odds. How could I know if quitting would be worth it?

To find out whether quitting my job would be worth it, I recognized I needed to try it first.

Here’s what I did:

1) Immersed Myself and Talked to People Who Were Already Doing It – When I considered quitting my corporate job, my problem was that I didn’t know many people who had escaped the confines of corporate life. It felt like I was pioneering something on my own, and I felt a little lost. Turns out there were many people out there that could serve as great role models.

I started immersing myself in this new idea of going solo by reading about and hanging out with entrepreneurs, bloggers, and movement makers and this eventually made me hungry for more. I started following a few bloggers like Chris Guillebeau, Jonathan Mead, Pam Slim, and Jonathan Fields. Then I started identifying people in my local community and reaching out to them to find out how they were doing it. This was enormously helpful in believing that I could do it too.

2) I Started a Freedom Fund and Paid Off All My Debt – This was a huge difference maker. I started saving a minimum of 20% of my income (and often more) once I had the desire to quit my job. I realize this may seem impossible for someone living paycheck to paycheck but this is what I did. I also paid off all my debt except for the mortgage.

When you’ve got several months worth of living expenses in the bank, you create more options for yourself. And if you get laid off tomorrow, you will have the confidence of knowing that you can survive and bridge yourself into starting your own business or finding another job.

3) I Simplified and Prioritized – Once I set my sights on leaving my corporate job and doing more meaningful work, I began to cut back on all unnecessary expenses and I prioritized what would allow me to achieve my dream. My wife and I sold one of our cars and began sharing one car that we already owned. Then, I set aside time to experiment with my new business idea to see if I could generate income with it. At first I didn’t think I had any extra time…until I made it a top priority.

4) I Started a Meaningful Project On The Side – I started experimenting with different ideas that I found interesting and that I thought people might pay me for. My first idea was a flop but I spent very little time and money trying to validate it. My second idea was a simple blog that discussed the very concepts that I was wrestling with; how to do meaningful work while also earning a living. This idea seemed to resonate with people so I started offering coaching services to others that also wanted to escape their corporate jobs.

5) I Began Creating a New Identity – By taking on a new identity, I was able to see what it was like outside the confines of corporate life while still getting my steady paycheck. I took on the identity of a podcaster and a coach and did these activities for almost a full year while still working full time. This allowed me to express my personal views freely before taking the next step.

6) I Created A Contingency Plan – My contingency plan was starting a business outside of my day job so that I could get hands-on experience doing something I enjoyed. It was nice to have a steady corporate paycheck which helped give me the funds to start establishing my business. It made it easier to hire a mentor and invest in some coaching and learning tools. I highly recommend Fizzle for amazing and affordable entrepreneur training and The $100 Startup by Chris Guillebeau.

7) I Got My First Paying Client – When I got my first paying client I experienced a feeling that I could have never imagined. I felt empowered in my ability to create my own future and I understood the necessity of offering something that others found valuable and were willing to pay for. You don’t have to leave your corporate job to get your first client. You just have to be willing to help someone do something that you have more experience with than they do.

My final thoughts:

Work at a job you enjoy doing, and build your business on the side until it gets so profitable you can’t help but quit. And if you happen to get laid off (like I did), then you’ll be in a much better position to choose whether you want to take your business full time.

Don’t be irresponsible with your life just because someone tells you to. If things aren’t going swell with your job, suck it up and figure out how to pursue new avenues.

Consult with people that are already having success with the type of business that interests you. Talk to them and ask them to shoot straight with you about what it really takes to succeed.

Calculate how long your savings will last if you go out on your own and make nothing.  Are you willing to tap into your 401k or get a loan if it comes to that? Be honest and give yourself the best chance at succeeding.

Being a successful entrepreneur is brutally difficult. It’s irresponsible to quit your existing job altogether without a financial safety net.

By all means, pursue the life that makes you feel alive. But do it in a way that gives you the best odds at winning.

Here’s to a meaningful and prosperous New Year!

Live bravely,


Question: What are your thoughts on quitting a job you don’t enjoy and starting your own business? What are your biggest fears and concerns?  

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