Ditch the Cubicle: How to Boldly Strike Out on Your Own

I was talking with a coaching client the other day — a 31-year-old guy who's set the goal of being his own boss by the time he's 35.

He wants to have multiple streams of income so he can pursue a wide variety of interests and regularly experience new challenges and opportunities. He wants to set his own schedule, make his own decisions about his businesses, and have the flexibility of spending time with his family. He wants to love his work and have fun at it every day.

How does this sound to you? Do you share this dream?

When he was a teenager, my client didn't have much ambition and didn't feel he had much potential for success, a belief reinforced by his parents and teachers. But sometime in his early twenties, he made the decision he could be successful — maybe even more successful than his peers. He got his degree and started working for a large software technology company, using some of his income to start a couple of small business ventures. He is now planning his next step toward entrepreneurship. I have no doubt that he will reach his goal of being self-sufficient by the time he's 35.

Many people dream of this freedom, but most of us hold back. It feels too risky, with no real guarantee of success. So what makes my client different? He's not necessarily smarter or more hardworking than the next guy, though he is smart and hardworking. I bet you are too.

Here's what makes him different. He has done one bold thing that sets him apart –he made the decision to be successful.

He set a goal for himself and isn't looking back, even knowing the risks involved. And that action is more than half the battle.

Does simply deciding to strike out on your own guarantee success? Of course not. You must assess the risks, complete your due diligence, make wise choices, and do the hard work daily. But think about the times when you have firmly decided to pursue something. Your passion, vision and hard work were amplified by the tenacity of your commitment.

Do you dream of ditching the cubicle to set out on your own?

If it seems daunting, take heart. The biggest thing standing in your way is the decision and the fear that surrounds making the decision. Here are some strategies around making the decision to be your own boss and how to get the plan underway.

Do Your Research to Start a Business

The lure of working for yourself is enticing, but make sure you know what you're getting yourself into. If you are going to start a business, there are many factors you need to evaluate, from the kind of business you will pursue to filing the right paperwork. Read and research as much as you can about the business, the start-up work involved and the income potential.

  • Here is an outstanding list of 50 Things You'll Need to Do to start a business. Many of these things can be done while you are still employed elsewhere. Don't give up your job until you have done your research and know exactly what it takes to start a business.
  • Here are some great resources for starting a business from the U.S. Small Business Administration.

What About Freelancing?

If you want to be self-employed without the complications and overhead of starting a business, freelancing is the way to go. Freelancers generally spin off from the work they have done as employees, using their experience and contacts to get started.

  • Freelancers commonly work in writing, editing, blogging, web design, graphic arts, computer programming, bookkeeping, or as a virtual assistant. They generally work on their own and have the luxury of working from virtually anywhere. But freelance work requires self-motivation, time management, and the element of uncertainty (like when is the next gig going to happen?).
  • If you are interested in freelancing or if you are a freelancer, I can't recommend Chris Guillebeau's Freelance Survival Guide highly enough. I have used it myself, and it is chock full of useful info. Check it out here:

Grow Your Business Without Killing Yourself

That Entrepreneurial Spirit

Maybe you are like my client and want to have multiple streams of income from a variety of sources. You can mix investing, consulting, coaching, freelancing, and business ownership. If you've been employed for years and have some experience under your belt, you can offer the variety of your experience to others and get paid well for it. You will enjoy new challenges, and by not putting all of your eggs in one basket, you'll be able to stay afloat if one stream dries up.

  • Leo Babauta, the founder of the wildly successful blog Zen Habits, makes a six figure income with a variety of income streams. Here's and article he wrote on creating multiple streams of income.
  • Chris Guillebeau has another great product for anyone looking to build a lifestyle business. His Empire Building Kit sold out during the first two releases. He now has it available on-going. Check it out here:

Empire Building Kit

Making the Decision

The biggest piece of moving forward on your own is making the decision. Nothing is guaranteed in life, even if you have a seemingly secure full-time job. If you truly dream of being self-employed, gather as much information as you possibly can before you set sail. If you don't discover any glaring red flags, at some point you have to launch. Here are some additional ideas for feeling better about pushing away from shore:

  • Take an assessment to see if you have the personality for self-employment. Here's a great assessment that has a very modest fee of of $12.95, and it only takes about 15 minutes.
  • You will need to have a back-up plan just in case things don't pan out. Make sure you don't burn any bridges with your current employer. In fact, ask them if they would be willing to keep the door open (in writing if possible). Make sure you have 6 months to a year's worth of savings to tide you over if necessary. Maintain your contacts from you previous work life. Here are some tips about creating a back-up plan.
  • Once you have made the decision, don't look back. Keep your eye on the prize, and like my client, make the decision to be successful. Will you have challenges and moments of doubt? Of course. But you can keep yourself motivated if you are proactive about it. Here's a useful resource to help keep you energized and positive about your work.

If you want to ditch the cubicle, don't just dream about it. Take action now to set the wheels in motion. Just beginning the research and planning will boost your confidence and set fire to your enthusiasm. Go ahead — be bold. Today's the day.

Download a copy of my FREE ebook, How to Live A Meaningful Life, and receive regular updates to my blog.

Click Here to Leave a Comment Below 27 comments


What a great timing! I’ve been thinking of being a freelancer because I want to more control over my time and prefer to work from my home than in my cubicle, and now I’ve made the decision to jump into the water with both feet. Thanks for the links, I’ll check them out slowly so that I can absorb the info. as much as possible. I’m familiar with Chris Guilebeau’s work, will take a look at them again.

Great post!

    Barrie Davenport

    Hi Maria,
    I’m so glad you have made the decision! The hard part is over. Now you just have keep taking the actions toward your dream. Let me hear back from you about your progress. I’d love to know how your adventure moves forward.

Wendy Irene

I was totally meant to visit your blog today! Love how the universe works like that  Over the weekend I started creating a resume to do freelance work because I was thinking it was an avenue maybe I should pursue. It was really wonderful to read your opinion on it! Thank you very much!
.-= Wendy Irene´s last blog ..Christmas in July – Leavenworth- Washington =-.

    Barrie Davenport

    That is so inspiring and gratifying to me! Thank you for letting me know that. I hope your freelance work goes smashingly :).

Chris Guillebeau

Hey Barrie! Thanks so much for your kind review. I’m so glad you liked the Freelancing Guide and the Empire Building Kit.

All the best,


    Barrie Davenport

    Hi Chris,
    Thanks for popping by! You produce such outstanding stuff with so much value. It’s easy to promote you. I have no reservations about recommending your products. Have fun on your travels.


your post is inspiring Barrie, i am so thankful to be one of the people who manged to make a living online, i hope i can continue doing so forever, its feels great to be self employed
.-= Farouk ´s last undefined ..Response cached until Tue 27 @ 8:46 GMT (Refreshes in 1.38 Hours) =-.

    Barrie Davenport

    Hi Farouk,
    Congratulations on your success as a self-employed person. Maybe you can share with my readers how you went about doing that.

Adena Atkins

Yes, yes, YES! Inspiring, practical, useful and specific. Terrific resource Barrie.
.-= Adena Atkins´s last blog ..You Have Suffered Enough =-.

    Barrie Davenport

    Thank you Adena. That makes my day! I hope you will pass the resource along.

cristi mercedes


great post today. filled with quite a few resources that i can make use of in my quest to change from worker to self employed writer / artist/ entrepreneur. love it when i can get good resources and input! another good one is the book, “The Creative Entrepreneur” by Lisa Sonora Beam. you can find it on her website or amazon. the site is just her name plus of course dot com. cheers!

    Barrie Davenport

    Thank you Cristi for you kind comments. And thanks for sharing that book. I will check it out!

Joe Wilner

Great post! I am on the same path as the gentlemen you spoke of, so this is very inspiring. Thanks for the great resources and all the details to make it happen. Thanks!

    Barrie Davenport

    That’s great Joe. Go for it! Please come back and tell us how it’s going sometime.


How did you know… I’m spending a couple days away from my current job planning my exit… between you and Chris G. I think I have some of the best teachers! Thanks for the extra boost today- it was certainly welcomed!

    Barrie Davenport

    I’m thrilled for you Laurie. Keep that boost charged up! You can do it.

Melissa Gorzelanczyk

Hi Barrie – I’m sure this post is inspiring a lot of people from their cubicles today. I quit my day job a little over a month ago and posts like this kept me going when the goal seemed so far away.

Your point about “choosing success” is right on … You have to boldly pursue what you want. Then things start to happen.

Have a great week!
.-= Melissa Gorzelanczyk´s last blog ..How to Grow a Prairie in Suburbia =-.

    Barrie Davenport

    Hi Melissa,
    I am so thrilled you had the courage to make that decision. I bet you haven’t looked back. Good for you. By the way, I am running your lovely article on Friday as a guest post.


This is my first time commenting on your blog, but I really like it. Ditch the cubicle and do it! I made that decision about 3 years ago when I left my job to travel the world for a year plus and am now working with my cousin from anywhere we can get Internet. I love it!
.-= Casey´s last blog ..webbROI- Going- but cant use Chrome RT @HubSpot Come &amp visit us at Digital Marketing World Social Media conference! http-bitly-dkRK7w mpworld =-.


Greetings! Very helpful advice in this particular post!
It is the little changes that will make the greatest changes.
Many thanks for sharing!


Leave a Reply: