Last weekend I was asked to come back to my alma mater, Indiana University, and give the closing keynote at their annual Women in Business Conference. The theme for this year was “The Thought Unknown” - which means that it is oftentimes so much easier to claim what we aren't good at or unable to do because claiming our strengths opens us up to vulnerability. The event aimed to cultivate conversations about claiming strengths and leading with empathy to develop professionally and personally.
Writing the speech ended up taking much longer than expected, as I went through iterations to distill down to a clear and impactful message. Looking back on my 11 years of experience post-IU, I found I had learned a lot about myself and had a lot to say for someone who is also an introvert. Below is the transcript I used, and which I should likely continue to read as a reminder that things often end up working out in the end.
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I wanted to thank Olivia and the club for this opportunity to come speak at the WIB conference - I graduated from Kelley in 2009 and credit my experience and time spent here with launching my career and setting myself up for success.
As I was thinking about what I wanted to say today, I truthfully went through several iterations. And I spent a little bit of time looking into Meg Jay and her work, since I know that was an influence for you all.
In her book, Jay talks about "The Defining Decade" and how the choices you make during this decade are much more important than you ever thought. Jay says that instead of giving advice she likes to ask her 20 something clients questions like "what is it that you want?" and "where do you want to be in ten years?" - the problem is, that is an often insanely hard question to answer - ten years ago I could have never predicted where I am today, nor that I would be happy doing it. Looking back it feels unreasonable that I was stressed about it, and unfair that adults put so much pressure on that without much help to figure it out.
At the start of this decade you haven’t actually been out in the workforce to try things out, test out your hunches. So I believe that when you are 20 you won’t know what your strengths and interests will be when you’re 25. But by the time you get to 25, you’ll have a much better idea of what those strengths and interests will be when you’re 30.
Why do I think that happens?
When you are deliberate about taking risks and exploring, you build the confidence to know what you’re good at and what you like. That’s when you get in the flow.
Let’s think about this as a metaphor: let’s say you step into a river on a paddle board. You’ve got a specific destination in mind and know you just need to paddle and stay afloat to get there. You’ll start heading down river even if you’re just sitting on the paddleboard, because there’s a current. As you gain balance you’ll start paddling and building some of your own momentum. Then you’ll see something on one side of the river that catches your eye, and you paddle over to check it out. You take a look but then realize maybe it’s not that interesting, so you get back in the main current. Next you veer off center and get stuck in some weeds for a bit. So you struggle, and after a while break free and get back to the middle of the river. By now you’re a stronger paddler and moving with, if not faster than, the current. And you actually pass by that original destination because you’re feeling good and want to see where the river takes you. And though you may stay in the middle the rest of the way, you know you can perform any number of maneuvers and get back on track.
Today I’ll share some stories from my twenties about being on that river, making deliberate choices to explore new areas, and ultimately becoming stronger and more confident in heading down this winding river of a career path.
As I mentioned, when I graduated I had a pretty clear path. And for a long time I was following that path. It was traditional, recognizable and felt important. I was going to work at Deloitte Consulting for 3-4 years, then get sponsored to go to business school, go back to Deloitte for a few years, and then by the time I was 30 I’d be moving into a more senior role in “industry.” Oh, and I’d probably meet my future husband in business school and potentially be married by 30 so I could hit that fertility peak in my early 30’s and start having kids.
Looking back at that plan now that I’m 33, overall quite a bit of that actually happened at a high level.
But there were many things I did along the way that helped me gain the confidence to make some bigger deviations from that in the past two years, most recently joining a small startup in an industry where I had zero experience, signing the offer letter less than a week after meeting the CEO.
At the time I may not have been able to tell you I was doing little experiments to discover and test out my strengths and interest areas. In fact, I actually felt bad about myself for not fully pursuing those trips to the side of the river to check out something interesting. Why was I going back to the center of this big boring river?
When I was 24 I had two friends get diagnosed with cancer. I was simultaneously struck with panic and motivation to go immediately pursue my growing interests in design and innovation. I was not happy in management consulting and I saw this news as a sign that I was meant to get out. I started researching design masters programs and decided to apply to a school in London in late winter. When I got in I was ecstatic. But as it got closer to making a matriculation decision, I wasn’t making any moves. I hadn’t thought about financing the tuition, visas, nothing. Doubt was steadily creeping in that this wasn’t the right decision - what would be my career options after? Was it a useful degree?
I was scared, nervous, sad, embarrassed to admit to myself that I wasn’t going to be pursuing this opportunity to a) study and work in innovation, b) live in London, and c) set myself up for working in the creative industry in Europe. I was nervous this was the only opportunity I would have to do those things.
The tipping point came in early June when I had to tell Deloitte whether or not I was going to apply for MBA sponsorship. Applying for GSAP, as it’s known, feels a little bit like applying to college – everyone in your start class is expected to apply, it’s a very public process. So if I didn’t apply for sponsorship, it would become clear to the entire office that I wasn’t planning to be at Deloitte much longer.
With much wringing of hands, asking advice of trusted peers, introspection, and some tears, I came to the conclusion that pursuing a MBA would set me up for many more future options. It would provide me a strong network, I would get some of it paid for, as a woman I felt particularly drawn to the idea of having a MBA should I ever have to leave the workforce. In some ways it felt like an insurance policy. Which, maybe felt boring?
So a few months after getting that acceptance letter, I sent in my decline, and then turned around to hunker down and start studying for the GMAT
In the vein of this metaphor, I had pursued what could have been a tributary, something leading me away from my original destination. I had proven I could get to the start, and it looked inviting, but ultimately too much was unknown about what happened down the line and I went back to the main river, a little crestfallen.
Fast forward to business school, and I was thinking about what I wanted to do for my summer internship. Unlike in undergrad, where I knew sophomore year what career I was going to pursue, and had my internship (and thus FT job) locked in the spring of my junior year, I was making a conscious decision to do off campus recruiting and pursue something less traditional. In a months-long exercise of telling myself “you’re doing the right thing, all the most interesting internships come in the spring!” and “don’t worry, you can always go back to consulting!” I was able to avoid giving in and applying to jobs through the career center, for the sake of safety and having something, anything locked in for the summer. As a type A Kelley grad who was used to having all of my career decisions made well in advance, it was anxiety inducing.
Come April, I did in fact see three different internship offers roll in. Venture Capital – which I had been pursuing, an ecommerce startup, and a luxury ecommerce company in Milan. That Milan opportunity really felt like it was out of the blue – they had reached out to me despite the fact I had zero experience in retail or luxury. Though I always found it alluring, I had almost dismissed it as a career because I just assumed it didn’t pay enough. Why would I take an internship in something that had zero ties to my future plans?
For one of the first times in my life I took a chance on an opportunity to pursue something just because it was interesting and unique and perhaps once in a lifetime. I was able to put aside, or perhaps ignore, the fear and anxiety that this wasn’t going to serve as a stepping stone. There’s always a way to spin a resume, right? It also wasn’t permanent. Relax Kendall! Go spend the summer in Milan.
Did I end up realizing luxury fashion was my true calling and move to Europe after graduation? No, though I did get a FT offer. Did I end up learning Italian and being swept off my feet by a native Milenese? No. Was it an often lonely and frustrating experience? For sure. But I proved to myself that I could move somewhere without knowing anyone, the language, or the industry, and be fine
I learned that not every work, educational, or personal experience has to have a predetermined purpose. It's about building that "identity capital" as Jay puts it. Something that adds value to who you are. Even almost six years later I am able to draw on that experience in both personal (cool first date story) and professional (proving 'resilience' in job interviews) situations
I had taken a little side detour on a creek by myself, had some fun, but then willingly came back to the main river, and was much better for it.
When I went back to Deloitte after graduating from business school, I networked my way into a group called Doblin, which was a small innovation and design firm Deloitte had bought while I was away at school. They were founded in the early 80’s and were using design thinking – similar to what Jess was talking about earlier – to help companies become more innovative and build innovative new business lines.
Remember back to when I thought that by not going to London for grad school I was giving up my only opportunity to pursue innovation consulting? Well, here I was after all, three years later.
It turned out that innovation consulting sat at the intersection of what I liked and what I was good at. The people were great, and largely very different from the management consultants I was used to working with.
However, despite being happy and doing well, I never made the full jump to be formally a part of, aligned to, Doblin. Even though I wasn’t planning to spend my whole career at Deloitte, I was still nervous of closing off opportunities and relinquishing my identity as a “strategy consultant.” I kept one foot on the Deloitte traditional strategy side, and one foot on the Doblin innovation side.
It was as if I was paddling down the river, feeling strong, with the Doblin team on a cool pontoon party boat floating next to me. I was asked to join the party and knew I’d fit in, but ultimately ended up staying on my paddleboard, taking some of the artisan food and drink with me as I sped out ahead of them.
Right around the time I turned 30, I joined New York Life in their corporate venture capital team. I had recruited for VC in business school and had now again decided that this was an eventual goal. I was very deliberate in how I sought out the job – I wanted to do innovation or new product development, and I had seen from Doblin that companies in financial services were willing to spend money on innovation. Within financial services, I had done work in insurance and actually found it pretty interesting. So, I decided on corporate innovation or corporate venture capital teams within insurance – both of which seemed like a good opportunity to step out of consulting, flex the innovation muscle, and work with startups. All of this would surely set me up to get into traditional venture capital.
In the year that I spent at New York Life, I learned a few things: 1) corporate venture capital is not a stepping stone into traditional VC, 2) innovation within a big company is only as successful as the CEO wants it to be, and even then, is a real uphill battle, 3) I missed my consulting colleagues. Needless to say, I feel like I spent the year banging my head against the wall.
This was one of the first times it was as if I had paddled towards what was a surefire, perhaps shortcut, to my end goal and gotten stuck. It was like a combination of shallow rapids and weeds. And what made that even more frustrating was that I was now 31 – I was supposed to have figured this stuff out now! I had made a decision on what I wanted and made what I though the right choice was to pursue it as a stepping stone. Turns out that stepping stone was instead slightly submerged rock and just ended up blocking my way. Help came in the form of the CTO, who essentially pushed me out of the weeds and back into the main current.
Once I decided to leave New York life, I also decided to leave the corporate world. In talking with others, I knew it would only get harder to get into the startup world as I got more senior. I started interviewing for consumer startups, largely in the fitness and wellness world. Think Peloton, Mirror, Bombas. Cool names with cool products, and I was getting out of insurance.
One day I was contacted by a headhunter that I knew, and he suggested I go in and talk with this real estate / insurtech startup. I told him that I wasn’t really interested in insurance stuff, but he pushed me to consider it. At that point I didn’t have anything else seriously lined up, so I went in.
I thought this was just a “meet the CEO, see what they’re about” type of deal. Instead, I ended up staying for almost three hours, met with four different people, and realized I was actually in an interview for a job I hadn’t even realized existed.
I left the office and later that afternoon the CEO emailed me and asked if I wanted to come in next week to talk about an offer. I was shocked. But also excited. Did they feel that confident about me, after only meeting for a few hours? Was this just how startups worked?
The following week I went in and ended up signing the offer a few days later. I knew nothing about real estate, had barely any time to do due diligence on the company, and had an extremely light weight job description. But surprisingly, I felt very confident in taking this leap. I realized that I was excited at the opportunity to figure it out as I went, and truly wasn’t sure what my next step would be after – but I knew that it would open a whole host of doors I didn’t previously have access to, or knew existed.
It was as if I had a destination in mind, but had paddled right on by with the comfort in realizing the river was much longer and winding than originally expected, and there were many more port cities to be discovered.
A lot of people will tell you both in college and upon graduation that you have to lean into, state your interests and goals and go pursue that. But that can be hard to do! And interests change, especially throughout your twenties. So be kind to yourself – over time you will build up the awareness.
And sometimes you have to really consider when people take notice of you and tap you for something. It could an opportunity you hadn’t seen yourself, or that you hadn’t considered for yourself. Those don’t come often and can lead you to discover new paths.
Little by little, by deliberately taking these small experiments further each time, you create the confidence that you know who you are, you know what you’re good at, you know what interests you.
The “defining decade” sounds intimidating, but I’m excited for you all and know you’ll be able to look back on it with recognition it all turned out in the end.
