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How to Make the Leap from Corporate Prisoner to Thriving Entrepreneur

As seen on Forbes.

Pamela Slim is the author of Escape from Cubicle Nation — how to make the leap from being a corporate prisoner to a thriving entrepreneur. One day Pam and I sat down to talk about how a person stuck in a corporate job can actually break free to start their own business.

Eric:  So Pam, welcome and thank you for being here.

Pamela: Thanks for having me. I’m delighted.

Eric: How did you become such an expert on escaping from cubicle nation to start and grow a successful business?

Pamela: Well, I started in the corporate world myself — but have been working as an entrepreneur for the last 16 years, with the first 10 as a consultant to corporations. I began to notice there were always people who would come up to me after a speaking event and quietly pull me aside and say, “How did you do it?  How did you actually leave to go out on your own?  I would love to but I just have no idea where to start.”

So I thought it would be interesting to start a blog and share information with corporate employees to address their unspoken fears and concerns about starting a business.

Little by little, I began to get more of an audience. Guy Kawasaki, a well-known venture capitalist and blogger, linked to a post I wrote — and things really took off. I’ve since worked with hundreds of people who are making the transition of leaving their corporate job to start a business.  

Eric: How important is it for a person when they’ve made the decision to leave corporate America and start their own business to look in the mirror and do a self-assessment on their passions; what they’re good at and basic planning as a first step?

Pamela: I think it’s critically important because there is a huge difference between being very dissatisfied with your job and wanting to quit because you don’t like it versus loving the idea of working for yourself and having a viable business idea you can actually execute.  In my book, I say “hating your job intensely is not a business plan.”

To use a dating metaphor — it’s almost like you want anybody who looks a little bit better than the current terrible relationship you have.  You might fling yourself into that person’s arms. Of course, people sometimes jump into an opportunity which sounds good; but really isn’t.

So you must take the time to honestly assess.  As you said — your interests and passions — but also what’s going on in the marketplace.

Eric: What can a person do to look at the market and do an analysis of whether their idea is going to be a feasible opportunity or not?

Pamela: The thing I trust most from experience are “small tests”.  You can have a big vision for what you might do, but you need to break it down into a step you can actually test in the market.  So if you think you want to have a carpet cleaning business, you would say, “Is there a way in my square block, within my housing development, to test it out?  Could I convince a neighbor or two to let me do the carpet cleaning to see what it actually takes to do it?” You want to test both the reaction in the market and also how you feel while you’re doing the work.

Tim Berry (Founder of Palo Alto Software) taught me a lot about business planning being an ongoing process of testing.  And I see sometimes people will spend a huge amount of time on their big business idea and doing tons of market analysis and reading every article they can and cross-referencing 20 different potential competitors.  But in the entrepreneurial world — that’s not how it works because two people can have the same business idea but so much of it is who’s actually able to execute and get it out into the market.

So you get out there. You try something. You test it. Get feedback. Make adjustments. Adjust your plan. Do another test and keep moving forward.

It’s also psychologically important to do small tests for people in corporate jobs — who can have some gigantic fears about making movement. Imagine you’re standing on a high diving board and you’re looking down at the water.  If you stare down at the water for an hour, your anxiety is going to increase the longer you’re standing there, right?  So the key is to get people in the water as soon as possible.

Eric: How important both psychologically and from a practical standpoint is it to take those first steps to start your new business while you’re currently working?

Pamela: I really like the idea of people working on what I call a “side hustle”. Now, it’s really important people in corporate jobs look at the employer guidelines of the work contract they signed.  You always want to have integrity in your full-time job and business.

But as a basic practice, I love the idea because you’re mitigating financial risk for yourself by working on your idea on the side.  You can slowly grow it and not be panicked about cash flow because you have your regular paycheck to take care of your expenses.

What I suggest for people is they set a time-frame — so it’s not just this open-ended thing which can go on forever.  But you might say for the next year, I’m really going to develop this stage of my business and then by this date, I’m going to check in and see if I’m ready to switch.  For some people, it’s when they have a certain amount saved in their account which feels safe for them to move out of their job.

For others, it’s when they’re earning the equivalent or a good strong percentage of what they’re earning in their corporate job so they feel comfortable enough to leave.

Eric: How important is it as you’re starting your business to set up milestones and goals?

Pamela: Incredibly important because otherwise, it’s really hard to get anything done.  And I certainly know people who are just super disciplined, who will take care of everything just because it’s on their to-do list. But many other people, when faced with their full-time job, spouse and family, can really get distracted.

And often in today’s work environment we get so obsessed by just continuing to produce where it never feels like it’s enough. Looking at our friend on the side who’s growing their business a little bit faster and think I must always be doing more.

So the best thing you can do is pace yourself with goals and milestones and get used to doing things on a reasonable schedule. You still have time for health, family and relaxation because that’s going to be a good rhythm to be a sustainable long term entrepreneur.

Eric: How does a person get into this rhythm to balance their job, new business and family?

Pamela: It’s really important to get super zeroed in on what the critical priorities and values are in each of those areas.  Ironically, it can make people hyper efficient.  People’s workplace performance can improve when they’re working on things on the side because they get used to cutting through the fat and not spending time on things which aren’t really important.

The same thing is true on the personal side.  If you’re volunteering in the PTA and have all these different activities, you really have to step back and say, “What’s really important to me?”. Especially for those folks like myself who have kids.  Often that’s a key priority where you know spending time with your kids is really important no matter how much work you have.

So it’s going to be different for each person and their own life situation. You have to get laser-focused on what’s really important to do in each of those areas and then pace yourself. Make sure you don’t schedule where you’re working full-time 8:00am to 6:00pm every day and then every single night from 9:00pm to 2:00am.  I know my friend Gary Vee (Vaynerchuk) would often talk about things like that in Crush It! — and I can appreciate his perspective.  But I also know it’s not sustainable in the long term.

Eric: What is something you would recommend for people who are going through the transition between full-time employment and their own business?

Pamela: Probably the biggest thing is to take a little bit of a break — to take some time in between leaving your job and starting your business where you can relax, putter around your house, pet your dog, get a massage, rest. And I actually recommend in that specific week or two — between the corporate job and your new business — of not doing anything with your new business.  Like really taking a full, complete break because otherwise you don’t let yourself transition fully.

And those clients who have really heeded the advice and just given themselves permission to take a little vacation — it has really paid off in spades in terms of how they start their new business.

Eric: If you could give only one piece of advice for a new entrepreneur, what would you tell them?

Pamela: I would say when you’re in the first stages — focus on cash flow. It is the life blood and sometimes choking point of so many businesses — even those having many opportunities. If you can’t really nail it and know where your cash flow is — it starts to set a whole bunch of things in motion which are bad. When people are new in business, they often get excited about everything.  Setting up all their systems and spending tons of time doing longer term social media content marketing, which of course is great in the long term.

But when I see people spending the first two months getting their logos designed and going to all these conferences, then it’s like, “Whoa, wait a minute. So what are you selling?”  And some people can’t quite articulate it. So you’ve got to nail that. You have to know who your customer is and what you’re selling. And then selling it successfully to get cash flow going.

Eric: How can people find you if they want to connect with you; learn more about you; or get help from you?

Pamela: My website is escapefromcubiclenation.com and is where you can find me. I also love Twitter, so people can find me @PamSlim on Twitter. Or on Facebook at facebook.com/pamslim.

Eric: Pam, again, thank you so much.  It has been a pleasure to speak with you and I look forward to continuing our connection and just working together to help entrepreneurs escape from cubicle nation and become thriving entrepreneurs.  

Pamela: Thanks for having me Eric.

NOTE: If you don’t know me, I’m Eric. Husband, father & life-long entrepreneur

If you’re an entrepreneur, let’s hook up.  Seriously.  Here’s a killer formula:

Your Wisdom + My Wisdom = More Success

My email is: eric at mightywisemedia dot com.  Let’s you and I connect right here, okay? Together we can really nail this thing.

(You can find me hanging out on Twitter @MightyWiseMedia.)

More Ways to Engage With The Above Article:

Listen to the full unedited interview with Pamela Slim right here: 

Audio – Full Interview with Pamela Slim – Author of Escape from Cubicle Nation

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About the Author: Eric T. Wagner is a husband, father and life-long entrepreneur. After starting multiple businesses, Eric is now focused on helping other entrepreneurs find the path to success in business and life. You can also catch his gig on Forbes or connect with him on Google+.

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