• Tips for Entrepreneurs

Ana Dutra's "Second Act" Tips for Entrepreneurs

By Ana Dutra

Last weekend I enjoyed my Kellogg MBA 20th graduation reunion at the same time that I celebrated my 50th birthday (but very few people knew that). Along with three girlfriends, I hosted a women-only Kellogg grads party.

All 45 women who attended our bash are in their late 40s, give or take a couple of years. They are all beautiful, successful, and fun to be around.

After a few glasses of wine and the usual catch-up conversations, the discussion quickly moved from the chronology of cool jobs in each woman’s life to agonizing discussions about “what’s next.”

I have to say I was expecting the topic to surface.

In fact, I probably teed it up on a few occasions since the “what’s next” dilemma has shown up almost too often in conversations with mature and successful women I coach or am friends with. I coined it the “Second Act Dilemma.” A delightful dilemma, in my opinion, because it provokes a stimulating internal dialogue when you have the luxury of making choices.

In my generation, women were provided with a clear recipe for life that equated professional and personal achievements with happiness and success. Women were told in more than one way, just as men had been, that the more they achieved the more successful and happier they would be.

And, like an army of determined soldiers, we dutifully went through college, applied for the most coveted jobs, worked really hard, collected a few additional degrees along the way, and climbed our life ladders, promotion after promotion. Some of us added a husband (or husbands) and a few lovely children to the mix. Executive women juggled work deliverables, motherhood, travel, family schedules, friends, health issues, and whatever else was thrown our way. We often knew what we wanted next, and we went for it.

Fast forward a couple of decades. We achieved success, our children are independent (some about to go to college themselves) and, like a tsunami, the restlessness about “what’s next” has hit us. That’s when the most logical and simplest question (“what are you looking for?”) becomes the hardest one to answer … and the most exciting, too.

Here’s the irony of life: At 30, we are either certain of what we are looking for, or we are open to a few different options, but we just don’t have all the ingredients yet. We are still missing the “right stuff” or enough experience. At 50, most women have the experience, the success stories, and the scars that go with them, but don’t know what they want their Second Act to look like. We are more selective, less excitable, more confident, maybe less romantic, but certainly more willing to explore possibilities.

The most enlightened ones among us have also parted with the need for titles and status, becoming more grounded and truly aware of what really matters in our lives, regardless of what matters to others or to society.

Throughout our lives and professional careers, we were told to “be focused but have an open mind.” At a more mature age, we earned the right to be somewhat unfocused, to experiment and take a few risks. Our minds can be as open as we want them to be. We are also more self-aware and knowledgeable about ourselves; knowing and accepting our risk profile is key to understanding how far we can and should push our own envelopes.

Reinventing oneself may have very different meanings to a person who is risk-averse as opposed to somebody who is a risk-taker or has a higher tolerance for ambiguity. And both are A-OK. …

So if you are trying to figure out what your Second Act will look like, pause and take some time—no, take a lot of time—to learn about and understand yourself first.

  1. Strip away all the preconceived notions about what you should be like, look like, and care about. Focus on who you really are and what will make you truly happy; “what is” versus what you were told it should be. And, once you figure yourself out, be kind and accepting of the wonderful “new you” you just discovered and the path that you will create for yourself.
  2. Know that your Second Act path can be a continuation. Or, it can be a complete disruption of your previous path.
  3. Think about everything you always wanted to do. But, for reasons that no longer matter, you never did. The list could range from learning an instrument, volunteering in a developing country, starting a business, to learning a new language.
  4. Try something new while still leveraging a skill or area you are really good and experienced at. This is especially important if you are hoping to walk down a completely new road that makes you uncomfortable—but you really want to try something different. For example, learn from the woman who, after a very accomplished academic career, decided to open a gourmet bakery. But since she didn’t feel comfortable being a newbie 100 percent of the time, she continued to teach on a part-time basis throughout her transition period. The combination of a familiar and a totally new activity provided her with a source of recognition and comfort that fueled her energy to be an entrepreneur in her mid-50s.

Figuring out our Second Act is hard work. But, hey, we are pros at hard work, right?

It requires time to pause and a lot of self-reflection. It is also very exciting and liberating. Not knowing for once what we really want next creates possibilities and opens our eyes to opportunities we would not have seen or considered before.

Enjoy the right you earned to be unsure, unfocused, curious, excitable, and fearless.

And when somebody asks you what your Second Act will look like, take pride in saying, “Right now, I have no idea, but I will know it when I see it.”

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