Ewa Jodlowska: from certainty to startup founder

As a founding member of the Sidebar community, Ewa has been a constant source of inspiration since the beginning. In her Journey, we explore taking great leaps, how she finds comfort in uncomfortable times, and the distillations of great leadership that can push any organization forward.

Sidebar: You immigrated to the U.S. (Chicago) from Poland when you were 5. Growing up, did you get any sense of how you fit into the world?

Ewa Jodlowska:  We immigrated to Chicago shortly after the Berlin wall fell. As a 5-year-old, I remember being shocked by being in a completely different place with completely different people. But I picked up the English language fairly easily by watching Sesame Street. No joke.
When you have immigrant parents coming to the U.S., there’s this expectation for achievement – to do better than they did. But I never had a push from my parents to do something innovative or entrepreneurial, like many parents might do. My family is actually very content, they don't necessarily attribute their success in life to their work. They work hard, but there’s a different sense of pride and how work fits into their life goals.
So where I'm at – midlife, changing careers, starting a startup – is very hard for them to believe. They’re supportive of my journey but they’re like, why would you do that? You had a job.

Sidebar: There's beauty in that contentedness too, right?

Ewa: Yeah, there really is.

Sidebar:  As a kid, did you have any idea of what you wanted to become?

Ewa:  I struggled a bit with that. My cousin – who is like a sister to me – is a teacher, so I thought I’d try that.  I enjoyed interacting with the kids, but I didn't love it. My job after that, I was exposed to programming, and that really set up the rest of my life. I got my bachelor’s in computer information systems, then took some masters courses in Denmark (I have dual citizenship). In reality, I learned the difference between what school was teaching and modern day development – it was like a five to ten year difference, especially what I was taught in the US. Fortunately, in tech there's so many people who have made successful careers never having gone to school, or changing roles midlife. It's all about networking and having the right people to support you through the process. And from there,  you can get wherever you desire on your own determination and follow through.

Sidebar: And that follow through led you to working at the Python Software Foundation for almost 14 years, topping out as the Executive Director. Most people I’ve interviewed have shifted jobs every 2-4 years.  I'm curious to hear your perspective on longevity with an organization.

Ewa: I started by programming registration sites for PyCon US, then helped with meeting planning. I took on more and more responsibility, until one day, I was at the top and there’s nowhere to go. You become the person who has the most knowledge – it's a great thing and also not such a great thing, for both myself and the organization. Every organization eventually needs a change of leadership that bring new life and ideas.
But I'm a normal person, and the fear of changing careers midlife was real. But so was the fear of being stuck. Eventually I found myself in a place where I wasn’t challenged anymore. At that point,  it was just time, and I could walk away happy that I got to be there that long and leave the organization in better shape than I found it.

Sidebar:  I love that answer, really self-aware. So you got to the top, you wanted something new and rather than going to another established organization, you decided to become the co-founder and CEO of your own startup. That feels like a pretty big jump… a risky reinvention, which is admirable. How has that transition been going?

Ewa: Reinventing myself was a big struggle at first because you go from being an expert at something to mediocre, at best. That's a huge, huge shift comfort wise, and the imposter syndrome sneaks in. Fortunately, my partner is in the same industry, and their encouragement and belief gave me strength. It’s much easier to reinvent yourself when you have a strong support system.
So it was a struggle at first, but when the client engagement part of the business kicked in, I was so rejuvenated and inspired. Those conversations underlined that there was a real need in the market, and we can make a big, positive difference in vendor security.

Sidebar: What are the must-have qualities of a great leader?

Ewa: A leader is only as good as the people around them. A great leader’s primary job is to help and support the people they're leading.
I’ve met the CEOs of some large companies in-person, and I’ve realized they don't have magical, unattainable skills. They’re as ordinary as everyone else, possibly with extra experiences. A major difference is they have really great people working for them, and they support those people in a way where they can actually retain them. A great leader puts their vision out to the right people, supports them effectively, and keeps them around. Any organization can get where it needs to go with that formula.

“A great leader puts their vision out to the right people, supports them effectively, and keeps them around. Any organization can get where it needs to go with that formula.”

Sidebar: I'm curious what you view as your biggest accomplishments?

Ewa:  I’m proud of gaining the knowledge to be comfortable with cutting edge technology. It’s become a lot more complicated than running your application from a data closet.  It's a huge, theatrical performance in my opinion - many small components need to work in unison in order for anything to work.
Also, my contributions to the Python Software Foundation have had a substantial impact on the community and the language itself. So that’s the major accomplishment. But I believe my startup will eventually become my big one.

Sidebar: And you just ran your first marathon, right? So that's got to be in there somewhere.

Ewa: Yeah! I've always been an active person. A friend of mine convinced me to run a half marathon with them this past June, and it was the hardest thing I’ve ever done. But after that I was like, I’m all trained up, I should just do a full marathon. Outside of rethinking that decision at Mile 22 of the Chicago Marathon, it was the hardest and best thing I’ve ever done. Now, I want to do the six major marathons around the world and then I'll call it a day (Chicago, New York, Boston, Berlin, London, and Tokyo). I haven't publicly announced it yet, but I will be running the 2023 Berlin Marathon for TEAM PAWS. I don't foresee myself being a lifelong marathoner because it's a lot –  you have to commit to a lot of training (not just running), you have to say no to friends that want to hang out on a Friday, and a lot of other sacrifices.

Sidebar: Go get them! So you're a Sidebar member, which means you're committed to growing as a leader. Any initial impressions?

Ewa: It was the perfect time for me to join Sidebar when I did, because I was going through a reinvention of myself, and the imposter syndrome was sneaking in really hard (as I mentioned earlier). It was the perfect time to meet great people and hear that I'm not the only one going through these things. Honestly, if that's the only thing I get from Sidebar…  knowing there are other people going through similar things, it’s already worth every dime and minute that I spend with my group.

Sidebar: I love hearing that. It's helpful to feel like you’re not alone. I wonder what you're working on improving with your group?

Ewa:  Number 1 is goal setting. When we did the group goal setting exercise, I noticed that I was focused mainly on fairly short-term work goals. There were a few people who knew their five year goal, ten year goal, fifteen year goal, and life goals. I was just like wow I gotta work on those goals. So that’s definitely been an eye-opening experience, in a good way. As a follow up, prioritizing goals is a huge one. I tend to get lost in goals, and from time to time need to reset my focus as to what is most important right now.
Number 2 is having a group that holds each other accountable. My field requires staying on top of things and giving myself permission to learn new things, which is very easy to put on the back burner while running a startup with things always on fire. But keeping that time blocked for myself is super super important, and I'm very grateful that my Sidebar group is helping me stay accountable to that.

Sidebar: Related question: can you think of a specific instance, where something you learned in your group changed the trajectory of your work or home life?

Ewa: As a group, we talk about different topics and someone inevitably recommends a book on the subject. Before you know it, all of us are reading the book. Prioritizing is a big thing – my to-do list grows faster than I can cross things off it. One group member recommended The One Thing. The book motivated me to get serious about long-term goal planning with my startup. Creating a roadmap is so much easier when you know where you want to arrive. I use my goals to refocus my attention and prioritize my time better – not just for my startup but also for my personal life. A recurring question in our Sidebar group is “What is the end goal?” I’ve noticed that I now ask myself that question regularly. It prevents me from overcomplicating things and getting bogged down by all the details.

Sidebar:  Have you had any life-defining moments or epiphanies that have shaped you into the person or the leader that you are today?

Ewa:  Getting out of my comfort zone has been a huge one. I notice that anytime I push my self out of my comfort zone, I grow. For example, at Python I had to get comfortable talking in front of 3,500 people. That took time – years – but I am sure that’ll help when it comes time to talk to investors.

Sidebar: That’s interesting, most people actively avoid discomfort but it seems like you've taken a growth attitude towards discomfort?

Ewa:  This is not something I've actually discussed with anyone, but throughout my life I changed from being an extrovert to an introvert. I can still be an extrovert, but it's on different terms. For example, after a big event, I need time to myself. Likewise, I won't schedule more than two social outings in a week because it drains me. Maybe I've mastered the art of putting myself out in uncomfortable spaces, but then also finding the space to heal and be ready for the next time. Creating that space has helped me navigate uncomfortable things and find the right blend of outward and inward time.
“Maybe I’ve mastered the art of putting myself out in uncomfortable spaces, but then also finding the space to heal and be ready for the next time. Creating that space has helped me navigate uncomfortable things and find the right blend of outward and inward time.”

Sidebar:  What's the toughest leadership moment you've had to navigate?

Ewa:  One of the toughest moments has been letting people go when they are not a good fit for the team. As a leader, I have a lot of empathy, it’s a positive and negative quality in my opinion. Empathy makes a team stronger and allows others to establish trust with one another. But sometimes tough decisions have to be made in order for the team and organization to thrive. I don’t think that’ll ever get easier either.
I have a notion that a future tough moment will be fundraising and the decision making that comes with it. The way we're approaching fundraising is very selective, and once I get there, I think that will be a very difficult part. I’ve done a ton of fundraising for nonprofits and sourced sponsorships, but VCs and startups are a different world.

Sidebar:  And that’s something your Sidebar group is able to provide inspiration and knowledge about?

Ewa: Yeah, absolutely. We have several people who have gone through the process, and every time they start talking, I'm like, hold on, I'm over here with my notepad writing everything down. I definitely know that when the time comes, they'll be there to support my fundraising efforts.

Sidebar: How are you, misunderstood?

Ewa:  I feel like people have a sense of how others perceive them, but how often is that accurate? In professional settings I have received feedback that I can be intimidating, probably because I can be very direct. I think most of that stems from my 14 years of working in an open source community. My silence probably contributes to that. I am more of a listener and doer than talker.

Sidebar:  What's been revealed since you've gotten to know your Sidebar group better?

Ewa: The best feeling happens when you can create real trust within a group. From that place you can share more honestly than probably anywhere else in life. It was awesome that within just a couple of meetings that trust started to happen with our group. You're hearing other people's stories, and they’re hearing yours, and we're all experiencing something very similar, just in different flavors. You can feel that resonate with everyone, and our group’s growth from there has been really awesome.

Sidebar: Amazing. You’re obviously an incredible person – you have big goals, you’re running marathons, and you're starting your own company. Where do you draw that energy and inspiration to keep growing as a person?

Ewa:  I think it’s just a deep desire to learn and experience new things. I'm sure many people can agree that doing the same thing every day gets boring. I have to change it up every once in a while. For example, I could have just continued doing my regular workout regimen for years and not done the marathon. And that would be fine. But instead, I got to experience something new, learn new things along the way, and meet new people. And that's really where I enjoy being.

Sidebar:  I love it.. Anything else that we didn't cover?

Ewa:  We've covered so much. This has been a fun interview. Best of luck.

Ewa’s Bylines

Ewa’s LinkedIn

Ewa’s GitHub

What is the End Goal?