Transitioning to Your Dream Career: Family Support Equals Business Success

By Seth Cohen

Making a shift in your career is hard. This is true if you’re changing companies or industries. It’s equally valid if you are moving from full time to retired or a second career — it’s all a little bit scary. As someone with experience helping executives transition to second careers, I speak to lots of people facing pinnacle moments like this, not only in their careers but in their lives. Even the cream of the crop, experts in their respective fields, need to think about support before they move on to what they think will be their perfect new career.

Getting the Solid Support You Need

I know how daunting a transition like this can be from experience. In my case, I had a lifelong itch to try my hand at something more entrepreneurial. Pursuing this dream meant leaving my full-time role and paycheck. Making this decision would not just affect me, it would affect my whole family. Instinctively, I called a family meeting — not just with my wife but with my three kids, who were teenagers at the time. I knew I shouldn’t make this kind of decision alone and if I wanted to make this professional transition, I needed their blessing. I also knew I would need their emotional support, but to get it, I needed to provide a strong business rationale.

“Us” Versus “Me”

I approached this event like any other business pitch and prepared for it. I articulated my business vision clearly. I created spreadsheets with our annual expenditures and the potential risks and rewards. Finally, we had a heated and honest Q and A. Yes, I told my kids, we will still have money for your college. No, I told my wife, we won’t lose the house. By the end of the meeting, my family understood the potential risks and rewards of this business venture, not just to me, but to our family. Everyone understood what I wanted to do, and everyone was on board with both the potential risk and the potential benefits. I was ready to launch a new business, but it didn’t feel to the family that I was doing something just for myself. We were in it together.

Of course, new businesses don’t always follow an easy path. In 2013, things were not going as well as I had hoped, and I was thinking of throwing in the towel. I drafted an email to my old boss to ask for my job back. I doubted myself, the business and my goals. We were away on a family weekend when I told my family I was ready to jump ship. My kids, in particular, were apoplectic. They reminded me that I was the one who had always preached that they should power through a problem, no matter how tough it got. They believed that I could make my business success even when I had my doubts. In the end, I never sent the email, and it still sits on my desktop as a reminder of what could have been.

Someone to Pick You Up When You Fall

Transitioning careers is not always smooth sailing and setbacks can be painful and unsettling. A good support system will encourage perseverance by keeping you in check when emotions run hot and color your decisions. During Eleven Canterbury’s dark period my family’s support held me strong and focused. I stayed in business partly due to the confidence my kids and wife had in me. It was the right decision. I doubled down in my efforts and figured out how to move my business from bumpy to success.

A Support Network Is Risk Mitigation

Communicating with your support network beforehand is mostly about risk mitigation. No one is going to have a big issue if everything goes swimmingly. However, when things don’t go well, you don’t want the people you care about to be blindsided. If you’ve communicated in advance the potential consequences, everyone will be going into this new phase with their eyes open. That makes any of the downsides, if it comes, more tolerable for them and you. And, it may also help you bear the emotional distress of business failure.

Who Loves You?

Your support network does not have to be just your family or significant other. It could be your close friends or anyone who shares your daily life. Whomever they may be, you need to make sure they are on the same page with you and your business goals. Starting this conversation may seem difficult. But I promise you, it will be helpful in the end. Here are some conversation starters and questions that could facilitate this dialogue:

• I think I’ve reached a pivotal time in my career and I’d like to explore some new options.
• I’m thinking of doing [blank]. Can we talk about what that means for me, but more importantly for us/our family/our friendship?
• If we do this, here are the possible outcomes for my business and our family/support network.
  Here are what I believe to be the probabilities of those outcomes.
• I think my work/life balance will change in x, y, or z ways. How do you feel about that?
• I may be working from home more often? Can our relationship handle this?
• If the plan goes belly up, this is my plan B. Are you comfortable with those outcomes?
• Do you agree with this course of action? Do you have any better ideas?

Make Sure It Becomes About “Our Success”

You’ll notice the last few questions are invitations into the creative process of the transition. It’s great to follow your dreams, but at the end of the day, you need to recognize that your decisions will impact the people closest to you. If you genuinely want to get buy-in, you need to be open and listen to their perspectives. Asking their opinion before you start is a powerful demonstration of trust. In part, this conversation is an acknowledgment that you are shaping your shared future. This should be an exciting time for everyone involved and by including your support network in appropriate ways, they can own part of that excitement.

Setting an Honest Tone

If you are not honest with your support network, there’s a good chance you aren’t being honest with yourself. However, by keeping lines of communication open with the people in your personal life you not only set yourself up for success, you also set the tone for your business. You want to find business partners you can count on to backstop you, tell you the truth, challenge you when you need to be challenged and lend a hand when you need one. But you can’t get help if you aren’t honest about what your needs are.

“I’m not ready!!!”

Of course, not every transition is by choice. There are many who make a move because they are following their passion but other times, the decision to uproot your professional life could be thrust upon you as is the case with mandatory retirement or a layoff. In this situation, having an open dialogue and the emotional support of your family or support system can play a critical role. It’s hard enough to make a transition when your heart is in it, but when a person is forced to make change they may be in a more fragile state. Time and time again, I’ve seen that having a solid support network is a vital part of a successful career transition regardless of what instigated the change. A personal support network can provide the emotional boost to help rebuild confidence, rethink career goals and move to a better professional place.

When it comes to professional growth, change is good. But it’s not easy. And in the end, if your business and career goals align with your significant other, your children, or anyone in your personal support network, you have a much better shot at weathering the bumps in the road that every career transition faces.

Seth Cohen is the Managing Partner of Eleven Canterbury. He was a member of the Group Managing Board and Head of Group Offshoring at UBS AG.