Turning 35 and Quitting My Job

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Last month I turned 35…. And I quit my job.* 

Tomorrow is my last day at the company that I helped build with my parents and the only job I’ve known for my entire adult life.** And after? Well, my family is going on a three-week South American adventure in a few days. But when we return in early February, if I haven’t found something, I’ll go into full-time job search mode. Wish me luck!

No, seriously, Ashley. You quit your job? What the hell are you thinking?

This was not an easy decision. It’s been on my mind for a long time. A year at least. Maybe longer. But not working for SAC was always one of those things that seemed unrealistic — how could I possibly quit the family business? — so I never let myself entertain the idea, and always shoved it aside. I had too much work to do, besides, and not enough mental bandwidth to consider something that would obviously never happen. But you go to therapy for work-related stress enough times and you finally have to look the elephant in the eye and ask the question: is it time to do something else?

Some people are unaware of the fact that our little family business was purchased by KnowBe4, Inc. at the end of 2016. After being courted by a few other companies in the space, my dad decided that KnowBe4, then still relatively new and modest in size, was the perfect fit for us. We became their first acquisition, and the rest is history.

Since then, we’ve doubled in size — and KnowBe4 has more than quadrupled! — and a lot has changed. Technology, vulnerabilities, elearning capabilities, client needs and budgets, and our own day-to-day operations. The industry itself has gotten denser, with more companies joining forces, merging, acquiring one another; the security awareness business looks vastly different today than it did 3 years ago, and even more so than when I officially came on board 11 years ago.

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While the spirit of SAC has prevailed through all of these changes, and we continue to deliver the engaging content we became well-known for, this is no longer a mom-and-pop shop. SAC is no longer my family’s company. We are part of the KnowBe4 family of publishers, and get to reap the sort of benefits that my parents could never have afforded to give our employees. And with great corporate benefits come great corporate responsibilities. The stakes are higher now; we have millions of eyes on our content, from around the globe. Client-needs are more diverse and complicated. The translation projects are larger in scope and frequency. Modern accessibility requirements compete with users’ desires for more robust gaming options. AR is entering the corporate training world, and VR might soon follow. No day is like another, and it’s all rather exciting!

But the messaging is the same as it has been for as long as I can remember. Security awareness has not really changed since my dad entered the business in the early 90s. Use strong, unique passwords. Be skeptical of things that seem too good to be true. Backup your data. Think before you click, and don’t click on stupid shit. 

And my heart’s just not in it anymore. I’m burned out. I don’t want to do this indefinitely. I’m ready for a new start. 

In the 11 and half years since graduating college, I’ve had so much fun working with my parents, and this job has given me tons of amazing opportunities for growth that I never planned for. I went from being the entire creative department to being the creative director of a very talented team; I’ve spoken at conferences and given webinars; I’ve unintentionally become a security awareness program expert, a skilled client liaison, and a member of upper management. But I’ve only done it all in the context of the safe, familiar, comfortable world of my family, how we work together, and the team we built. I’ve literally worked for my parents’ company, in some capacity, since I was a kid.*** I’ve never stepped out on my own, worked with people that I didn’t hire, or worked on projects that weren’t, in some way, my idea.

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In other words, I’ve never left the nest. I’ve just built bigger and more nests nearby. It’s time for me to spread my wings and see how far I can go.

Those I’ve  told about this decision have asked what I plan on doing next…. and that’s a great question. Because I don’t know! I guess it’s time to figure out what I want to do when I grow up. I love the logistics of managing remote teams and the challenges of nurturing remote culture. I thrive in fire-fighting mode, finding creative solutions to balance client needs with the abilities of my team. Refining workflows to improve inefficiencies is incredibly satisfying to me****. And I believe in hands-on leadership, jumping into the trenches to help my team whenever necessary. No task is too small and no hat is too big; if it needs doing, I will get it done. Furthermore, I’m industry agnostic***** but I want to work for a remote-first company that embraces the power and flexibility of distributed teams. 

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I didn’t expect to but I have felt liberated since making this decision in November. Lighter. I sleep better. The day I told my parents, a huge weight was lifted off my shoulders. The day I told my staff was much harder and very emotional — for many of them, SAC was their first job out of college or freelancing, and I was their first boss. But at the end of the day, after many conversations and hugs and tears, I could finally see the light at the end of the tunnel for the first time in a very, very long time. And I felt relieved.

In some ways, I feel like I’m going through a divorce — an amicable one, but it’s still emotionally draining and there are dozens of loose ends to tie up. I won’t be talking to these people every day, seeing what they create, helping them put out client fires. I have to let go of my creative control, and no longer have a say in anything that SAC does going forward; like I said, it’s no longer my family’s business, and I think I might grieve that for a while. But I’m also single and ready to mingle, metaphorically. For the first time ever I’ve had to make a resume. I’ve been the interviewer dozens of times, but I, myself, have never had to answer the same questions! It’s all so scary and exciting and nerve-wracking and thrilling, and I can’t wait to see where I land.

I know that SAC will continue being a leader in awareness content and one of the premier publishers of the KnowBe4 family. I know everyone at SAC is going to continue kicking ass in their roles, and that the people I’ve gotten to brainstorm and create and work with all of these years are only going to thrive. I am 100% confident in the abilities and talents of my successor; Kayley was my first full-time employee, the first person I hired, and she’s helped me grow so much over the years (both professionally and personally). It’s been amazing working with someone who just gets my brain. It’s been so rewarding to have the opportunity to grow in our roles, together, over the last 8 years, which is not something many people get to do. I’ll miss working alongside her side, having her as a constant sounding board for my half-formed ideas, and not having to explain when my language breaks because she already understands what I’m trying to say.

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When I went full time at SAC in 2009, it was supposed to be temporary until I figured out what I wanted to do with my life; I did not plan on that role blossoming into a career. But here I am, a decade later, incredibly heart-burstingly proud of the small but mighty company that my parents and I built together. My mom retired last month, and my dad is off playing with brain science and VR to improve adult learning, and this company is no longer ours. I’ve learned a ton since the acquisition, and grown in my leadership more than I thought I could, but I’m ready to move on. I’m proud of what we built — the content, our reputation, the team I hired and trained and grew — and I am ready to see what else I am capable of building on my own. 🙂 

But first, I need to pack for a three-week trip with my parents and brush up on my Spanish. ¿Dónde están los pingüinos?

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Footnotes:

*Technically I quit it several weeks before turning 35.

** I worked two months at Books-a-Million in 2008, had a few short-term video editing gigs and freelanced graphic design for many years post college. Aside from those brief professional endeavors, I have worked for what was my parents’ company, literally, since I was a teenager.

***Not even kidding. I remember many an afternoon in my pre-teen years folding, stapling, and labeling physical newsletters to be mailed. I helped my mom pack hundreds of boxes of my dad’s books to be shipped. As soon as I had a car, I became responsible for all shipping of said boxes. Before I graduated high school, in the pre-Twitter and RSS feed days, I became responsible for writing the weekly news digest we emailed to our clients, something I was usually rushing to finish late Sunday night. And I can’t tell you the number of powerpoints I had to dress up for my dad’s presentations. 

**** I do this in my personal life too. No joke, one of the *most* satisfying things to me is to take a long list of errands, and figure out the most efficient and timely path in which to get them done. I give myself bonus points if the journey ends with a fun lunch or cocktail somewhere. Justin can attest to the many Saturdays we have spent accomplishing my to do lists with Swiss-like efficiency and how happy that makes me.

*****Though I’d really love to leave cyber security.