career development


Kerry-241 (2).jpg

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.   


Alisa spends most of her non-working hours with her pup.

Alisa spends most of her non-working hours with her pup.

on going after your target position and keeping your eye on the long game


A mutual friend connected me with Alisa Frederick (Kate Brown – go read her post if you haven’t already!), and I’m so grateful that she did. Like Kate, Alisa is a bit of a unicorn in that she is one of very few women in a very male dominated world—Alisa works in finance. She is a Partner and Managing Director at Caltius Structured Capital, a firm that provides subordinated/mezzanine debt, minority/structured equity, and unitranche solutions for middle market companies. (Is it obvious that I just copied that explanation from Alisa’s LinkedIn? I don’t know what most of those words mean, but essentially, her company invests millions of dollars in businesses to facilitate things such as buyouts, recapitalizations, growth, and acquisitions.)

In addition to being a powerhouse finance exec, she also happens to be an incredibly thoughtful, kind, and self-aware individual that is generous with her time and wisdom. During the course of our long brunch together, she shared enough career lessons for a few blog posts, but I chose my favorites to share with you here. I hope you get as much out of them as I did.




Although Alisa has been in the finance world for many years—nearly two decades just at Caltius—Alisa revealed to me that earlier in her career, she never would have imagined that she could be a partner at a private equity firm. She didn’t even study finance in college! She graduated with a political science degree, but followed her interest and applied for a bank credit training program in NYC. She didn’t have the right qualifications on her resume, but she went for it. When the interviewer asked her what she would contribute to the role, she responded, “I can write well and I’m good with people.”  As it turns out, that was the ticket. They knew that they could teach her the banking credit and leadership skills, but her other skills were seen as particularly valuable.  

Alisa told me, “It doesn’t really matter what’s on your resume. If you see a position that excites you—go for it.” This urging reminds me of the research that revealed that men will apply for a job if they feel that they fulfill 60% of the qualifications while women won’t spring for the role unless they’re confident that they meet 100% of the requirements.

We women have a terrible habit of closing the door on ourselves before we even try and walk through it. We make the [often false] assumption that we will be found wanting, and instead of letting the interviewer be judge of that, we eliminate ourselves from the running without giving ourselves a real shot.

There are three things that employers assess when going through the interview process with a candidate: 1) qualifications, 2) desire, and 3) fit. Notice that being qualified is only one factor that they consider. Especially earlier in your career, culture fit and a desire to do the job are often weighed much more heavily. So, be a little bolder and apply for those roles that excite you.

Sure, Alisa also recognizes that there are roles and industries that really won’t give you a second look if you don’t meet their criteria, but she makes a good point here as well: It’s still worth putting yourself out there. The process of reaching for the role may be what forces you to take a look at where you are and make necessary adjustments if that’s really where you want to go.



For many young ambitious women, the overthinking and self-doubt doesn’t stop once we’ve landed the job. Alisa was telling me about some mentorship that she’s done with young women in the business program at my alma mater, and she reported that many of the young women are just panicked. Everything feels so high-stakes to them when it comes to their careers.

I love Alisa’s perspective on this. She says to “recognize the longevity of your career and all that you have ahead of you. Look at each little thing ahead of you—each ask, pitch, project—in the perspective of your career. It’s just so immaterial. Not everything is a throw in the towel moment.”

In Alisa’s career, there have been countless times that she could have fallen apart if she hadn’t had this perspective. She’s responsible for winning business for the company, and there are dozens of deals that she loses every year. Fortunately, she recognizes that winning or losing those deals has very little to do with her. Not everything is going to be a win—or even needs to be.

She illustrated this concept by comparing it to a game of golf. You can hit some terrible shots and get a really crappy score on a hole, but then—you get to choose whether or not you take that with you to the next hole. What’s done is done; that next hole is still waiting there with a new opportunity for that hole-in-one. 

In the long careers that we can expect to enjoy, there will be things that go wrong. We will make mistakes or poor decisions that have consequences, but it’s what we do in those moments that matter. Our thoughts about these situations have the power to stall us in our careers, or allow us to keep pushing on and growing. It’s important to keep the mindset that we can learn from these experiences and know that there’s always the next “hole” (or project, or client, or pitch…) that we get to take another shot at.

This is called resilience and persistence, and it’s critical for achieving all that we hope for.


Another antidote to the anxiety and self-doubt that so many of us experience is to get clear on the skills and perspectives that you bring to the table that provide value in your team or organization.

Earlier in Alisa’s career, she was insecure because she thought she had to emulate her male peers and be a “schmoozer” to win business and grow her realm of influence. But, through time…and trial and error…and self-reflection, she found that the way that she can provide the most value is by doing what comes most naturally to her. Her team needs her to show up the way that she does best. She’s not flashy or loud; she balances her team by being the thoughtful listener, the one attuned to her clients’ needs. She’s a trust builder. She’s the level head in the room that helps her and her partners navigate tricky situations.

It’s a beautiful irony that it’s actually the things that make her different from her male peers that make her most valuable to the team and company. At a certain point, she started to see herself in that role, and the insecurity started to melt away. She told me, “The result would have been so different without me,” and that’s where she puts her focus.

Finding your unique value is a quest that involves paying attention along the path of our careers to find the confluence of where our skills and what energizes us creates the greatest impact in the organization that we work in, and then continually working to flex and grow those.