Women in Leadership: Kristen Holt

This is the second blog in a series we are calling Women in Leadership.  The goal of this and future blogs are to introduce you to women in all stages of their career. To get a sneak peek into their insights and frustrations. Our hope is these interviews will provide you with a connection, an insight that will support you in your career. Please reach out to us with your thoughts at  


Kristen Holt is the CEO of GreenPath Financial Wellness, which is a national non-profit that supports people’s lifelong financial wellness through holistic financial education and coaching. In this interview, Holt details her career and her philosophy of trusting that things will work out even during difficult times. A truly inspirational woman, Holt emphasizes that women leaders are put on this earth for a reason, and we are so thrilled that she is a part of our “My Career Matters” initiative as an Act III – Who Runs the World (Working Women!) Ambassador.  

What is your current position and how long have you been with GreenPath Financial Wellness?  

I’m the CEO at GreenPath Financial Wellness, and I have been with the company for almost three years. 

Did you have a plan when you started planning out your career?  

I thought I did, but I didn’t think big enough about my career when I first started out. My original goal, as a CPA, was to one day be a controller. And then I landed my “dream job” at 23 as a controller, so I realized I needed to set bigger goals and have more confidence in my capabilities.  

Tell us about your philosophy of believing that things will work out?  

I have always believed that everything happens for a reason.  And, looking back at my life, I always can see how all the dots connect. Steve Jobs talked about this during his 2005 Stanford commencement address, and it really resonated for me. He said, you can’t connect the dots going forward, you can only connect them going backward. For example, I can see now that when I thought my life was going to take me to Boston to run a company, but then the deal fell through, it was because 3 months later I was going to meet my husband, and we have now been married 15 years and have two amazing daughters.  If life had taken me to Boston, this never would have happened.  It is easy to connect the dots going backward.  But, while you are in a challenging situation, it doesn’t make sense and it is scary.  But after you are through it, it all makes sense and the dots connect – hindsight, right? My whole life, looking backward, I can see the dots connect, and it has confirmed my belief that everything happens for a reason. What I have had to learn is to trust that it will work out even when you can’t see how that is possible.  

Has your connect the dots philosophy always held true during your career?  

In hindsight – so far, yes! As I said, I have had to learn to trust that this is true! I had a very successful career, at a young age.  By 28, I was senior vice president and chief financial officer at a global, growing, entrepreneurial company. I was the youngest officer in the history of the company, and I loved my job. I had reset my career goals by then, and I was determined that I was going to be CEO there one day; I was going to retire from there with 40 years of service – I actually used to calculate it!  But, as time went on, it went from being my dream job to a job more about survival until retirement. I had lost my passion for the work and I didn’t feel like my work mattered. But I was convinced this was my only option. I had invested my career here, and the thought of making a change was terrifying. And, as everyone knows (but I guess I didn’t), when you are working in a place of fear, without passion, it shows, and it affects your performance. You can’t keep this a secret. And so, inevitably, at 38, I was fired from that same company, and I thought my life was over. 

I couldn’t see an alternate future.  You can’t connect the dots going forward, and I didn’t trust that things would work out. Now, looking back, this too worked out for the best.  

Tell us more about how getting fired was a good thing for you.  

If I hadn’t been fired, I wouldn’t have taken the time to discover my own personal passions and learned that I could live them every day. I wouldn’t have learned how energizing and fun work can be, and that it should never be about surviving. I would have missed the opportunity to work with an amazing leader in an impactful non-profit where I learned about using human centered design to solve real problems that affect real people – by learning more about what people need and working to meet their needs. And I wouldn’t have been led to my current role, as CEO of GreenPath. 

I can honestly say, over the past six years, since making the job change that was not originally my choice, I have grown more as a person than I did in the first 17 years of my career. I have learned so much, and I am so much happier.  

You spoke about passion earlier; can you talk a little bit more about this?  

Well, until 2012, I never thought about finding my passion. I now realize how important finding your passion is. You go to work every day and spend so much of your life at work. It shouldn’t be something that you are doing to pass the time until you retire. I learned that I needed to get clear on why I am here on this earth. And that by being clear about this, I can live a much more intentional life, a much more fulfilling life. By being clear on my passion, I am a better mother, a better wife, and a much better leader. 

My own family, and close friends, notice a real difference in who I am as a human. I am happier and energized, and it is because I am doing work that aligns with my passion and values.  

How do you go about finding your passions?  

So how – well it starts with understanding your strengths. At United Way, I was introduced to Gallup’s StrengthFinders. The principle of strength-finders is this: the secret to success and happiness is knowing your strengths and being able to work on your strengths every day. When you work on your strengths, you are energized, you lose track of time, you have fun, you enjoy life. I took the StrengthFinder assessment and discovered one of my strengths is called “Significance”. What it means is that I have an inner need to leave a legacy, to do work that has a profound and lasting impact. And, it is also a rare strength, the 2nd rarest strength to show up in the millions of people who have taken the assessment. By understanding this, everything clicked for me. I was able to connect more dots – looking backwards of course. I was able to understand why having meaning in my work was so critical for me. It wasn’t just a desire to do good things or to help people – everyone has that. This was something bigger – doing work that will leave a legacy is what drives me internally; I believe it is why I was put on this earth. And if I’m not working to fulfill that purpose, I’m not at my happiest. And knowing it is a rare strength motivated me too – I feel like I owe it to the world to fulfill this rare strength I was given.  

Can you explain a little bit more about this philosophy?  

For me, my “no matter what” in life is simple – I want to be happy. But how do I live this “no matter what?”  Well – it makes me happy to work on really big, nearly impossible problems that matter to people, to work on problems as a team, to ideate, to try, to take risks and chances, to fail along the way, to learn, and to, over time, get some big wins to celebrate. This is when I am working and using all my strengths at the same time – that is powerful! By having this “no matter what”, it helps me gut check every day. If I’m not happy, I need to understand why, and then figure out what am I going to do about it. I’m no longer going to wait for it to happen to me, for my change to get forced on me, I’m going to make the change every day. It’s also about spending meaningful time with my family, connecting with them, and not being so stressed at work that I make my family unhappy by bringing that stress home. And it’s about knowing I have to take care of myself, before I can take care of anyone else. I measure my happiness mostly by how well I’m sleeping at night. That is my easy metric, and if I’m not sleeping well, I need to make an adjustment somewhere.  

What advice can you give to other women in the professional world?  

My advice to other women – go take the StrengthsFinders assessment. Read the report. And see if through it, you can identify times in your life where they were truly energized and excited, lost track of time, happy. And see if you can connect the dots to your strengths. And then, try to do that work, every day. Don’t do work that doesn’t give you energy. You will be most successful, and happy, if you are working from a place of strength. Have courage, take action, and trust that it will work out for the best. Even if you don’t take the assessment, you can probably identify times in your work when you have felt this energy, and times when you have not. Try to figure out what caused you to feel good and energized – and do more of that.