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on dreaming big & setting yourself up for success


Kerry is inspiring for many reasons, but I think the thing that I find most impressive about her is that she has done the work to put herself on a personal and career path that truly fulfills her.

It wasn’t always that way. As an ambitious woman in the world of finance, for much of her career, she was motivated by external factors—status, money, promotions, and recognition. After years of grinding and achieving what she reached for, she found that being at the top was ultimately very unfulfilling and empty. (I mean, let’s be clear…she felt good about what she’d accomplished, but also realized that that wasn’t enough for her.)

So, she got curious and explored where the feelings of dissatisfaction came from. Thanks to some soul-searching, she realized that she wasn’t connected to a higher purpose. After getting a coach that helped her tap into how she could matter on a greater scale, she knew that she was ready for a bigger, bolder step in her life and career. A little while later, when her company got acquired, she got the sign she needed that it was time for her to make moves.

It was then that she started WoMAN – the Women of Mergers & Acquisitions Network. WoMAN is a networking group for women in finance where Kerry fulfills some of her higher purpose by providing members not just the opportunity to connect with each other, but also to learn and serve others. She intentionally created WoMAN with three pillars – Info, Connect, and Serve to help her members to connect with their heads, hearts, and hands.




Now that Kerry has WoMAN up and running, she has identified a super ballsy goal for WoMAN’s growth over the next couple of years. It struck me as she was telling me her plans, that this lady has no question that she will achieve it.  

Many women I know (myself included) are incredibly creative when it comes to imagining the worst. As soon as an idea strikes, we invent a million reasons that it would never work.

When I asked Kerry for her take on this not-so-rare phenomenon, she boiled it down to love and fear. When we have something that energizes us, we love it. But very quickly most of us flip to fear. Kerry says it comes down to which of those two reactions we choose to feed. She suggests that people acknowledge when those fear thoughts come (without ignoring or shunning them, or alternately getting consumed by the fear), and from that place take control of it.

Kerry talks about seeing the fear, understanding where it came from, conceding that it may be valid—but still choosing to act. This reminds me a lot of what Katica Roy said in her Doyenne Chat about feeling the fear but doing it anyway. I also recently saw a quote by Katica that emphasizes this concept, “Your brain is not wired to make you happy, it’s wired to keep you safe.” 

Those fear feelings are natural. That doesn’t mean that we need to let them run the show.

What I noticed in Kerry’s response was that she has an innate confidence that she’s allowed to have what she’s reaching for, and she also trusts in herself to know that she will accomplish what she sets out to do.

When you embark on a new journey, there will be countless unknowns, but there will always be one variable that is held constant – you will be the one taking the journey. There’s power in that.



Kerry admitted to me that while it comes fairly naturally to her to let love win out over fear, she is not fearless when it comes to reaching her ballsy goal. However, she also acknowledges that who she becomes in the process of striving for that goal is really where her feelings of success will come from. Kerry told me, “I have not met the me that has reached this goal.” On the path to reaching her goal, she will become that person.  

She continued, “Even if it takes me much longer to reach my goal, everything will have worked out just how it should have.” 

It’s easy to get singularly focused on the end goal, and miss all the rich learnings from the journey there. I think it’s particularly seductive for perfectionists, who see setbacks and detours as failures along the way; but, I love Kerry’s framing of the whole situation! She’s got her goal—and that motivates her—but how she’ll measure her success is based on who she becomes and what she learns in the process.

I think this concept is also a very powerful, practical antidote to the fear we talked about in the first takeaway. I’d venture to guess that the roadblocks and detours that we anticipate or imagine are the very things that we fear and use as evidence for why we can’t reach for our lofty goals. However, if we see each of those events as opportunities to grow into the person or professional we want to become rather than threats, what is there to fear? Seems like you’ll either succeed or grow.


This last Takeaway almost felt like a throwaway for Kerry—like it was so obvious to her that she was ready to blaze right on by it. But it was such a smart tactical next step for achieving goals that I doubled back to it and pumped her for more info.

Kerry said that once you choose love over fear and decide to act, the next step is to surround yourself with the people that will help support you to achieve your goals.

Too often, women think that if we are to find success, that we need to do it on our own. Like, somehow our achievement is invalid unless we can take credit for every lesson learned, every milestone hit.

I asked Kerry for more details on this idea of building a group of people that can help you get there. She approaches this with intentionality and makes sure there are a few key members in her support crew:

  1. The Pro
    When you’re setting out to reach for a new goal, you may not have the skills or knowledge needed to get there. Kerry suggests bringing in someone who has been where you’d like to go and make time to learn from them.

  2. The Cheerleader
    Making moves and taking risks can be exhausting and painful work. Make sure to have someone in your inner circle who understands your vision and potential and keeps picking you back up when you fall on your face.

  3. The Creative
    This is the person who understands your potential and can mirror back to you all that you can be. They see things from a different perspective and help you push your ideas to the next level.  

  4. The Realist
    It can also be extraordinarily helpful to have someone that you trust to tell it like it is, who can pressure test your ideas, and help identify roadblocks and brainstorm solutions. This is not your “yes man”, but rather someone that pushes you to do even better.

It’s a natural tendency to surround ourselves with people who are similar to us, but that probably isn’t going to be particularly helpful if you want to do big things. Kerry shared a quote with me from Jim Rohn, “You are the average of the 5 people that you spend the most time with.” You might as well make sure that that inner circle includes the people who can help you accomplish what you want most.