What if you had to graduate from your job?

Matt Ragland
3 min readDec 9, 2017

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Photo by Cole Keister on Unsplash

At ConvertKit, we will regularly have big team discussions about non-traditional topics. The kind of things that aren’t normal to talk about at work.

For example, here’s a question posed to the team recently…

If we told you you have to graduate out of the ConvertKit team after five years of working here, and we could magically make sure you can start any business or land any role you want, what would you want to do after leaving?

Similarly, if you were independently wealthy, what would you do for work? How can your work help you on the path to doing that work in the future?

It’s an interesting and thought provoking experiment. When you see the Bureau of Labor Statistics report the average job tenure is 4.2 years, the experiment becomes realistic.

Thinking about your current role and how it aligns with future goals is important. If the work you’re doing now puts you on track for opportunities later, then work in the present will improve.

Ironically, I think that if more directors asked this question and helped their employees develop these skills, it could lead to less turnover. I have a lot of respect for the leaders at ConvertKit to be willing to ask a question where the end result of the thought is “then you may decide to leave”.

If I had to graduate ConvertKit in 5 years

I would be happy going in a couple directions.

  1. Going back to the beginning and leading a success team in a similar position to ConvertKit when I came on.
  2. Working as a product designer or manager that also has a big hand in customer research and development.

What I really enjoy is working with people to help them grow, take action, and succeed, then working on a product to help them make progress. The primary way I’m doing that now (and can continue) is by using my experience with customers to help design solutions within the app & supporting resources.

I love to learn, which is good because to get any kind of job in product or design I’m going to need to spend the next 3 years learning how to do it!

If I was independently wealthy, I would honestly keep doing many of the things I do now. The big exception is if I decided I was tired of spending most of my time looking at a screen and started a business rooted in a physical location. It could be a co-working space, fitness gym, or teaching center. I love giving people the space and structure to reach their own goals.

A longer term goal is that I’d like to start a semester-at-sea or NOLS style program that serves 18–25 year old young men. It would provide mentorship, skill development (if you wanted to focus on coding/writing/whatever for 4 months), and service (partner with NGO’s in other countries). To be honest that’s probably 10–15 years away and I’m fine with that.

Aligning your career with your company

Hitting publish on those words for the rest of the company to see was still a little nerve-wracking. The biggest worry I had was “finding out” that goals I had wouldn’t match the needs ConvertKit had for me. What happens then?

It turns out that this worry was unfounded. At a company like ConvertKit, which values employee development and growth, if they don’t know where I want to go, how can they help me get there?

Defining my goals in the ConvertKit world has already been a healthy experience, it’s allowed us to be on the same page about how my career development aligns with ConvertKit’s needs. I’ve begun working on my first real in-app project with onboarding, you can check out my progress at my YouTube channel!

Defining your goals can be scary at first, because you’ll be planting your flag and saying “this is what I want”. But without clear communication of where you want to go, you won’t have much help getting there.

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Matt Ragland

Onboarding Lead at ConvertKit. Started a weekly vlog this year to teach everything I know, check it out: https://www.youtube.com/mattragland