Looking In: How to look inwards to determine what matters to you in your career

Mollie’s last project at IDEO involved one of her all-time favorite topics: the future of urban mobility. Her client, a car manufacturer, had an opportunity to enable smooth commerce in cities through new models of transportation while also creating jobs and improving equity in lower-income areas. Mollie and her team couldn’t wait to get started. They had so many ideas already!

But there was a critical step they needed to take before hitting the pavement: they needed to understand the specifics of what their client wanted and what they were good at. They started by interviewing a dozen people across relevant parts of the organization, asking questions like, What are your team’s current objectives? What capabilities do you have in-house that you’re eager to utilize in this work? What can you not do well and will need to outsource? What constitutes a good return on this investment, and how much budget do you realistically have to spend?

From this research, they painted a picture of the client’s competitive edge and priorities, and saved valuable time that might have been spent on ideas the company would struggle to complete. At IDEO we call this type of research Looking In. It’s the process of understanding the client’s strategy, goals, key metrics, and core competencies to ensure we don’t pursue an idea that isn’t the right fit.

Slow down to speed up

When it comes to careers, Looking In is a critical first step, however, it's also the most forgotten. We rush into combing job postings and submitting resumes because it’s exciting, and it makes us feel like we’ve taken action.

We’ve both done this too many times to count.

Like in high school, when Charlota, unsure of what the right job was for her, asked her career counselor for help and received a long list of standard professions which she dutifully researched, wondering when the spark would hit.

Or Mollie, not knowing how to determine what she wanted to do after college, followed the free wine and cheese to the campus recruiting events and wound up working in accounting (a great place to start her career, but not the best match for her interests).  

Mollie’s career exploration upon leaving business school looked a lot different. Guided by her coach and her crew, she took the time to reflect on her past work. She thought about when she’d felt the proudest, the most driven, and the most in-flow. She also considered when she’d been frustrated, bored, or stuck. She wrote everything down, and she tracked her engagement and emotions over several weeks to see what kind of work was sparking joy. This audit didn’t give her the answer, or even concrete ideas for jobs, but it did identify a few themes and constraints.

For example, she realized her favorite days were the ones where she had lots of meetings with different teams. The energy-filled discussions and the variety of topics covered in conversations with different parts of the organization (in this case London Business School) made her feel connected to her peers and immersed in campus life. She realized she needed a highly collaborative job, and one with a lot of variety within each day. 

How do you look in to discover what you truly want in your career? 

There are so many fun ways to do this! Here are a few of our favorites, including some from the Crew coaching program:

1. Start a work journal

Get yourself a new notebook or find your favorite digital tool and carve out ten minutes every evening to write some key findings from your day. Note down your favorite moments from the day, the times you felt energized, the types of activities you were doing and how they made you feel, and any times when you felt annoyed or checked out. It’s up to you what you capture. The goal is to be more conscious of what’s making you feel fulfilled and happy, and what’s not.

Be detailed.

We suggest doing this for three to four weeks so you capture a variety of days and activities before stepping back to look for themes. 

2. Conduct a calendar audit

Look back through your calendar for the past two weeks and count the number of hours you spent... 

  • Working alone vs. working with others
  • Doing vs. thinking
  • Focused on one task vs. multi-tasking
  • Using your existing skills vs. doing something for the first time

Now, with some numbers in your hands, capture if this time ratio felt right to you.

Would you rather spend your time working alone, focusing on one task, getting in-flow?

Or maybe you feel energized when planning and strategizing rather than executing?

Capture which activities left you satisfied and which left you flat. 

3. Ask others to describe your strengths

It’s often difficult to have a clear view of our own strengths. They can get muddled up with what we like doing or think we ought to be good at. To get a different perspective, ask a handful of friends and colleagues to share what they think your strengths are. 

Here’s a prompt you can use:


I’m working on gaining a better understanding of my career strengths and interests. I consider you a good friend / a colleague I enjoy working with – and I would really appreciate your honest feedback on these questions:

  • Which five adjectives would you use to describe me?
  • Which activities and skills seem to be easy for me that others might find hard? 
  • Can you tell me about a time you saw me excel?

Give them the freedom to be honest and thorough. Perhaps send them the question in advance and then take them out for coffee. Capture what they tell you in their words, try not to synthesize it yourself as you write it down. Once you’ve done several of these, ask yourself what themes are emerging.

What’s similar or different to how you viewed yourself?

An example application of Looking In

A recent crew’er, we’ll call him Jordan, is a successful designer and strategist. Throughout his career, he’s been approached many times by friends and former colleagues offering him jobs that he’s been pleased to get and has said ‘yes’ to. He joined Crew because he was starting to realize that, while happy to receive such great offers, he’d never stopped to think about what he actually wanted from his career before saying ‘yes’ to the next thing. By doing the important inner work (including the activities described above), he learned “to know when to say No,” and decided to search for jobs he wanted instead of accepting the ones that came his way. This led him to apply to a dream role at a crypto company, which he got!

When do you use Looking In activities?

These activities are useful to repeat whenever you find yourself at a decision point in your career. For example, when pondering things like:

  • Should you take that promotion at your current job that comes with a new set of responsibilities?
  • Whether to take a leap and start your own business.
  • Do your days at work feel dull and predictable, or too fast and exhausting?
  • At this point in your career, do you want to optimize for income, status, or freedom? 

Looking In activities offer a great recalibration that will help you make sure your next career decisions are in tune with your wants and needs.

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