believing in yourself


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.


Kate repping some Boulder Organic! Soup gear in her hometown - Boulder, CO.

Kate repping some Boulder Organic! Soup gear in her hometown - Boulder, CO.

on self confidence and modeling what to do when you’re wrong


I can’t think of a better person to kick off my return to writing this blog than Kate Brown (not the Governor of Oregon, but another very impressive Kate—the Founder and CEO of Boulder Organic! Soups). I took a little break to get settled in my job and life after the whirlwind that was the MBA program. But now, I’m back at it and looking forward to learning more from kickass female bosses, and sharing those takeaways with you.

Now, let me introduce you to Kate.

Kate is the type of person that makes everyone she talks to feel like the most important person in the room. She is warm and charismatic and incredibly generous. She’s also a super savvy individual and a very hard worker that has created a successful business from a humble little venture that started in her kitchen.

Here’s the story of how she created and grew Boulder Organic! Soups: When Kate’s young daughter got her tonsils out, Kate ran to the store to get some soup that would be easy to swallow and would free Kate up to so that she could just spend time with her daughter while she recovered from the tonsillectomy surgery. What she found at the store was congealed, canned, concentrated “soup” that was full of preservatives and unpronounceable ingredients. So, since she couldn’t find what she was looking for, she decided to do something about it. She started making soup out of her kitchen for friends and family, and after a Whole Foods buyer heard about it, the rest was history.

Flash forward 13 years, and you can find her delicious soups in plastic tubs in the refrigerated section of grocery stores across the nation.

In Kate’s life before her soup venture, she was a therapist, which I think you’ll see evidence of in the takeaways from our convo that I share below. I think you’ll agree that she’s incredibly self-aware.  I hope you enjoy her perspective as much as I did.




While more and more women are finding their way into leadership in business, manufacturing is still very much a boy’s club.  So, when I asked Kate about her experience being a woman in leadership, I was really surprised by the response that she gave me. She said, “I just don’t accept pushback or negativity. It’s just so stupid.”  

That’s a nice sentiment, but I couldn’t wrap my mind around its simplicity. I asked her how she doesn’t get pissed off when she’s underestimated because of her gender. Her response is the real nugget: “I have complete 100% confidence in myself. I would have died on the vine if I had looked for outside sources of approval. Looking to others for approval is a guaranteed heartbreak.”

Throughout our careers, we’ll all be presented with countless occasions when our skills and qualifications are doubted, or when the people we look to for support are not in our corner. One of my favorite quotes on this topic is from Supreme Court Justice Sonia Sotomayor, which goes like this, “I do know one thing about me: I don’t measure myself by others’ expectations or let others define my worth.” That’s profound (and also much easier said than done).

There are a few strategies that I’ve come across that can help in this effort that I’d love to share with you:

  • Recognize when you’re outsourcing your worth – Pay attention to when you’re looking to others to validate your value. This is the very first thing to get a handle on, and it may be hard at first since many of us have been hustling for approval from others, especially those in power, since before we can remember.

  • Get clear on how you want to measure your worth. When I think about the things that are truly important to me, qualities like grit, generosity, hard work, resilience, optimism, and being a good teammate come to mind. These are some of my values and things that I choose to attach my worth to. If I’m out of line with my integrity on these things, then I’m in trouble and I need to work to find my way back to them.

Then, there are things that don’t get to determine my worth: things like how good I am at statistics, how eloquent I am when addressing a crowd, how good I am with managing the big picture (or the small details), or even how good I am at my job.

You see, these are things that I do, not things that I am. That’s why, even if I am falling short and want to improve in any of these areas, I get to choose to not allow any of them to affect my worth. It’s important to draw the distinction between those skills or traits that you want to develop from those things that you hang your worth on. This way, you can acknowledge the areas where you want to grow and lean into them without finding yourself in a full-blown identity crisis.

  • Question feedback – both the bad and the good. When you get negative—or positive—feedback, ask yourself, “Is it true? Is it helpful? Is it guiding me in the direction that I want to go?” If not, disregard (yes, even the compliments). Since you’re not hanging your worth on this feedback (see previous bullet point), then you’re able to assess feedback in a productive way.
    Now, why question positive feedback? Because it’s fickle. If you depend on the positive feedback of others to feel good about who you are and how you’re doing, then what happens if they change their mind? Or move on to the next thing?

  • Finally, get choosy about who’s opinion matters to you. Here’s a new concept for a number of you: not everyone’s opinion matters. Kate has this concept on lock down. She is selective when it comes to listening to criticism. In the case of her business, she’s worked hard to develop a strong leadership team who she trusts and welcomes feedback from and has created open lines of communication with her staff, but when it comes to people that underestimate her, she says “I know who I am. I feel totally uninterested in what someone else thinks.” She knows that she’s acting in line with her values and integrity, and that’s all that matters.



Because Kate is incredibly honest and totally relatable, in the next breath after telling me the value of trusting in her confidence in herself, she also shared with me that sometimes she trusts her north star too much—even when she’s wrong, she feels really right. (See? #relatable) 

While she has a sense of humor about this aspect of herself, she also pointed out that this tendency can be dangerous when you’re in a leadership position—it’s not like people are lining up to tell the boss how wrong they are.

I love Kate’s perspective on this. She opens herself up to feedback and says, “You have to be willing to not have it be an ego dig. There’s nothing wrong with being wrong. I don’t have to be right all the time.

Before I could really process that concept, she continued, “Being wrong in a leadership position is really important—you get to model for your group how you handle it. How can we learn from this?” 

There are a couple of key learnings here. First, it’s okay to be wrong sometimes**.  I know women often feel the pressure to have it all right, all of the time. But, there’s also value in being wrong—it allows us to model for our group how to handle it. There is something really powerful about a person that is able to acknowledge where they went wrong, own those mistakes, and then take the strides needed to right the ship. In addition to setting the tone for others to take risks and make moves, it also builds trust. Because she’s honest with her people even when it’s hard, they know that they can also own up when they’ve made an error.

**Note: Kate and I did talk about how not all company cultures support this, but as a leader, she feels it’s important to set the tone that it’s okay to be wrong—as long as it’s handled appropriately. This may be something to consider when evaluating culture fit at a new job, or something to model if/when you’re in a place of influence.


Heather Dupre

on forging your path and not taking "no" for an answer


Heather is best known for co-founding Egg Strategy– a successful marketing strategy agency that she led for 16 years. She was able to retire last year after growing Egg to include three offices, in Boulder, Chicago, and New York City, and developing an impressive portfolio of cutting-edge consumer insight and strategy work for brands including Hershey’s, Neutrogena, Clinique, and Remy Martin. She now teaches marketing classes to lucky undergrads in the business school at CU Boulder (and will soon be teaching innovation – her sweet spot). 

Her path started long before her time at Egg, though. Her story is one of reaching for ambitious goals, not taking “no” for an answer, and believing in herself against the odds. She had to overcome personal and professional obstacles to create a great life and career for herself, which you’ll learn about below. In addition to her inspiring story, I also got the goods on her philosophies on leaning in and advancing one’s career. Read on…




Heather got married when she was still in college, which wasn’t all that uncommon at the time. A few years later, her marriage started to crack and at the age of 29, she found herself divorced with a little boy to support, and a fairly worthless degree in Art History. She had an urgent realization that she needed to figure out how she was going to support her little family. 

She decided that an advanced degree was in order, so she studied hard and did well on the GMAT, and got into the Kellogg School of Management at Northwestern University. For most of the three years she was in her program, she attended classes at night and worked out of her house during the day raising her son and doing graphic design. (Talk about grit...)

When one of her advisors at Kellogg told her that she was too old to get into advertising, she set out to prove him wrong. Weeks later, when she received her acceptance letter from her target advertising firm, Leo Burnett, she marched down to her advisor’s office and taped the letter to his door along with a note that said, “Don’t ever tell anyone that they can’t do something.” 

Her persistence and moxie remind me of a quote that I recently came across by Oprah Winfrey. She said, “I am where I am because I always believed I could get here.”

She didn’t let setbacks constrict her world around her — she believed in herself and her abilities, and whole-heartedly pursued what she wantedIt would have been easy for her to feel like a victim of her circumstances following her divorce, or to reign in her goals following the discouraging feedback from her advisor, but she doubled down and pursued her objectives with all her energy. 

We all have the power to develop this type of grit in our own lives. It requires making the decision to believe in our abilities over and over, with each new challenge, so that we can keep driving toward our goals. (Remember, beliefs are just habitual thoughts.)



Refusing to take “no” for an answer is a theme in Heather’s career. After excelling at Leo Burnett, she moved to the brand side and had successes with all sorts of consumer products companies, including food, household products, spirits, and pharma. 

My favorite story that she shared with me is from her time at Kellogg’s. 

She had research that showed that people purchase a surprisingly large amount of their Rice Krispies to make Rice Krispy Treats. Given this info, Heather knew that she could grow the brand by encouraging people tomake more treats. Her idea was to create festive-colored Rice Krispies that people could easily use to make even more special-looking Rice Krispy Treats (with that “oooh-ahhh payback factor”) around the holidays. 

We all have Heather to thank for these glorious treats.

We all have Heather to thank for these glorious treats.

History has proven that this idea was genius, but at the time, she got major push back.

But, she didn’t back down. Heather knew that the idea was worth fighting for.

So, without any support from her immediate higher-up, she got the right people on her side to figure out the formulation and how to put holiday Rice Krispies into testing and then production. In the first year — without any advertising — the Christmas colored Rice Krispies flew off the shelves. They became an important part of the portfolio for years. 

Heather’s refusal to take “no” for an answer with the Holiday Rice Krispies resulted in a big win for Kellogg’s, but it was definitely a risky move. 

That brings me to the next takeaway…



Heather has often been called a “change agent” in her career. She told me she thinks that label might be a little strong, but I suspect she is just being humble based on her advice:

 “You need to believe in yourself. Be cognizant of the corporate culture, but be willing to push sacred cows out of the way – in a way that’s acceptable. There are times when getting your opinion out there will result in you being taken much more seriously and respected.”

A lot of Heather’s success has to do with the fact that she spoke up. She bravely stood by her ideas and vision because she knew they would have an impact for the company. Speaking up and advocating for her ideas allowed her to be seen as a leader, and she was able to accomplish great things throughout her career as a result. 

If you aspire to leadership, you need to believe in your ideas and abilities and make your voice heard — and, there is a careful balance to strike

It sure is appealing to zero in on that sexy part that says, “be willing to push sacred cows out of the way”, but don’t overlook the fact that it’s sandwiched between two really important statements. 

It is critical to promote your agenda in a way that is acceptable within your company’s corporate culture. You need to use discernment to know when to push the boundaries, and when to pick your battles.

One more thing on the subject: don’t forget that if you want to make changes, you need to bring people along with you. Heather never could have brought her festive Rice Krispies to market without the support of a handful of people in other departments that believed in her vision. You need buy-in from others to become an effective “change agent”.