12/18/2014 09:11 am ET Updated Feb 17, 2015

The Road Between Employment and Entrepreneurship: Getting Family and Friends to Journey With You


I distinctly remember the day I sent my Dad a message that I would most assuredly be quitting my job before the end of the year. It had been something I was working towards for a year and a half; but I'd not yet set a date for handing in my notice. It had gotten to a point where I was living in the half decision of fully intending to leave my job, yet not making any significant progress towards that desire. I set a date of August 30, 2013 to make my decision real. To help me concentrate my efforts on actually making it happen.

A few hours later, my Dad Skyped me. I think he was worried that I was having some sort of personal crisis. While I don't remember our entire exchange, I distinctly remember firmly telling him "It's happening." I said this with so much resolve that he could only respond with "Okay."

My Mom was also worried. Recently asking her to provide an honest reflection of how she felt when she found out I'd be quitting law she wrote:

I will admit I was concerned because you had told me financial stability was important to you . . . I knew you had worked really hard to finish law school (a long time dream). I was very concerned that you would lose everything that you had worked hard for and I did not want you to lose anything.

My parents' response wasn't surprising to me. After all, I had worked hard to become and thrive as a lawyer. Counting law school, I'd spent 11 years crafting a professional life and career for myself, and I was about to dismantle it all in one fell swoop. Moreover, I'd be redesigning myself as an entrepreneur with all of the risk that it involved.

Realistically there is no sure thing in life. Optically speaking though, steady employment "appears" safer than risky entrepreneurship. So in conversations with friends, family and colleagues, I would find myself justifying my reasons for making the switch. I eventually learned that this was more about me dealing with my own fears and worries then their perceptions (more on that later). That being said, I think it is helpful to think about how to broach the subject with individuals. It's always nice to have support. It's also helpful to know whose opinion actually matters.

Whose buy-in do you really need?

In other words, who will most directly feel the ripple effects of your decision to quit your job to start a business? In my case, I was a single woman with no children or dependents counting on a steady income but I know this isn't the case for everyone. In working with individuals with families to support, I've observed that it's helpful to have a series of open conversations. There's the expression of the desire to quit and start a business, everyone's feelings about it, ideas about how it could work, and a decision. It could be a decision to stay put; a decision to wait until a better time; or a decision to take the leap. Every situation has its own level of complexity (and simplicity), and it's about making ones way through the challenges (and opportunities).

It all starts with you. Are you willing to open up to the key people who would be affected by your decision to start a business? To share with them your reasons for even thinking about going this route? Getting a dialogue going can help you make a decision that you and the key people in your life are comfortable with.

Paint a full picture

If you do decide to open up, it's ideal to give a full picture of where you are with your ideas, thoughts and musings. Situations rarely ever have clean, hard lines. Perhaps there are times when you feel the strong pull of entrepreneurship, and other times when employment seems like the better course. It's totally normal to go back and forth. Opening up about all of this can help other people understand where you are coming from. (It can also be quite cathartic). Quitting employment to go entrepreneurial is not an easy decision and it's not supposed to be. I suggest providing the full landscape of where you are, with all of the "messiness" involved. It's part of the process and can help you feel more resolved, whatever you decide.

Apart from those who will be most directly affected by your decision, who else in your life do you feel safe opening up to? Who will create the space for you to be completely open and honest about your thoughts and feelings? Who will be constructively supportive?

You don't have to please everyone

At the end of the day, you're not going to please everyone with your decision. It seems obvious, but it took me a long time to grasp this. When sharing my plans, I would subconsciously look for a gleam of approval in others to assuage my own fears, doubts and insecurities. It took me some time, but eventually I realized that this was because I was projecting my own fears onto others. If they weren't convinced, then could I really make it as an entrepreneur?

Once I understood the dynamic I was creating, I was able to save a lot of energy. Instead of spending precious moments trying to convince others of my decision, I was able to spend my time more wisely (e.g., preparing for the day when I would hand in my notice and branch out on my own). I was also able to use conversations as a "mirror." Whenever I was triggered by something someone said, it helped me realize that I was grappling with a lingering fear about whether I could actually transition smoothly from employee to entrepreneur.

Are you ready to fully face your deepest fears about traveling the road between employment and entrepreneurship? What triggers you when talking about this to others? This can be an incredible opportunity to resolve your fears, doubts and insecurities.

At the end of the day, this is all about powerfully resolving yourself to your decision (whatever the decision may be). If you do decide to travel the road between employment and entrepreneurship, having a tribe of supportive individuals can be an invaluable asset.