The Career Question You Need To Be Asking

written by  Ryan Seamons

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Where do you see yourself in 5 years?

This is simultaneously the most common and the worst way to begin a career conversation. It’s not that we shouldn’t make plans. I’m a big fan of long term goal setting—my wife and I have a 30-year plan and I regularly review my yearly goals. But starting career conversations as if we have a crystal ball brings a host of issues:

  1. Many people have no idea where they see themselves in 5 years

  2. Even for those who think they have an idea, reality is often very different than the plan

  3. We expect managers to coach and advocate, but many managers have no idea how to actually do this.

I often had a “good” answer to the question of where I’d be in 5 years. But looking back I was not only wrong—I was magnificently wrong. Had I taken that answer as my only career guidance, I would have missed out on many of the best experiences and opportunities that have built my own career.

There’s a better way to figure out what to do next. It starts with this simple question:

What’s most important to me in my career?

Not what title or company do you want, but what attributes of work do you actually care about?

Do you value autonomy or exploration? Fun or achievement? Inclusion or competition? Reputation or learning?

None of these are about right and wrong. There are certain things we each value more about how we work. And sadly we rarely take the time to reflect on which ones are most important, why they are important, how we tell others, and what action we can take now. Even when we do, it’s a fairly abstract conversation.

This is why I’ve been working on Career Cards. I want more people to have space + direction to reflect on what matters most to them about their work.


The team I work with has drawn from proven elements used by other card sorts including Knowdell, Stanford Values, and Instructure Drivers. We honed our own 50 words, defined multiple exercises, and tested with over 100 people. And then we added what everyone said is missing from existing card sorts: a conversation guide + a premium training series to make the most of the conversation and have a clear plan for what to do next.

I’m keeping the training short (a series of 2-5 minute videos) and packing it with career development insights from my experiences including:

  • working at LinkedIn during the hyper-growth years

  • running my own company

  • having some bosses who sabotaged my progress

  • helping dozens of people get jobs they wanted at top companies (including Amazon, Cisco, American Express, Lamda School, and Google)

  • getting my first internship with no experience

  • switching roles, industries, and companies multiple times

  • getting a job offer from Google

  • managing 10+ teams throughout my career with consistently positive feedback

And most importantly, while I’ve experienced many ups and downs like everyone does, I’ve found fulfillment throughout these experiences.

I’ve had multiple people advise me to price this at $200+. That said, the full price for the deck + conversation guide + premium training will be $97. Before we launch in September, you can pre-order the deck, conversation guide, and premium training for $47.

Early adopters have commented on the benefit not just for a conversation with their boss, but also with peers and even their spouse.

You can check out our website and pre-order at

Regardless of whether this is right for you, I hope you take time to reflect and act on the best question you can ask about your career: what’s most important to me about my work?

About the Author

Ryan Seamons
writes about more human approaches to modern management.

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