how to figure out what you want - by Hilary Gridley
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how to figure out what you want<br>stop looking inward. instead, go collect one hundred data points.
Hilary Gridley<br>Jun 30, 2026<br>∙ Paid
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The summer cohort of How to Be a Supermanager with AI starts in one week. Over 300 leaders have taken it to sharpen how they manage with AI, and at 4.8 stars it’s one of the highest-rated courses on Maven. Enroll today.<br>Level up your leadership<br>I graduated from college with a literature degree and an understanding of the job landscape that was largely based on the career tracks you read about in Richard Scarry books.<br>Everyone in my family worked in architecture. My older brother showed early talent for drafting; he landed in a prestigious firm right out of school and has been there ever since, an impressive 15-year run with one employer. This talent did not trickle down; when I played The Sims, designing the house always felt like unnecessary tedium standing between me and my ultimate goal: creating a series of bizarre situations for my Sims to navigate. So with architecture off the table, I set out to develop a concept of “jobs.”<br>My research consisted of exactly two coffee chats.<br>The first was with a family friend who worked in publishing, a line of work that seemed fitting for a young English major. He sat down and looked over my resume.<br>“It doesn’t look like you have done any internships,” he observed, correctly. “Because you were…teaching scuba diving in the Caribbean?”<br>“Yes,” I chirped. “I learned many transferrable leadership skills. Did you see I was also a bartender? I am good under pressure.”<br>He gazed into the distance, as if looking into the future and finding it grim.<br>“Listen, Hilary. This industry is tough, and getting tougher. There are maybe ten good jobs available to new graduates, they are very competitive, and they do not pay well. You will not make any money for the first decade of your career, and you will not have job stability. Perhaps you should reconsider.”<br>So reconsider I did.<br>The second coffee chat was with a senior executive at National Geographic, a meeting generously arranged by my brother’s then-girlfriend, who used to babysit the executive’s kids. Despite recognizing my good fortune at the connection, I did not rise to the occasion. He asked me why I was interested in working in TV, and at that moment it crossed my mind that, come to think of it, I was not particularly interested in working in TV at all. The conversation stalled out from there.<br>I graduated on the heels of a recession, in 2010, so I was not alone in struggling to find a job. Maybe, I decided, I would be better off traveling around the world for a year, and then giving employment another go when the economy picked up. Then, by a stroke of luck, my dad told me that someone at his office had received a mailer for an organization called Ocean Conservancy, and he suggested I email them about an internship. How clever! If my burgeoning scuba career did not qualify me for a glamorous role in book publishing, here’s something it did qualify me for. I sent the webmaster a cold email, and soon enough, I was the new webmaster. I made $40,000 a year, and as long as I fired off five tweets about the ocean every day, nobody gave me much trouble.
When I got engaged, I set out to find a wedding dress. Prior to my engagement, I had not thought much about what I would wear to my own wedding. I browsed Pinterest a bit, located a variety of local bridal ateliers, grabbed my best friend, and tried on a couple dozen dresses over the course of a weekend. I ended up deciding between two wildly different dresses, and ultimately went with the very first one I tried on.<br>I loved my wedding dress, and I loved my first office job, but when I made those choices, it felt a little like spinning a globe and picking my destination with my eyes closed. This is destabilizing for me, as someone who likes to have a strong point of view, and enjoys the work that goes into developing one. So over time, I started studying how people develop a strong point of view about what they consider good.<br>What I have found is that their approach is remarkably consistent, even across domains.
I am often asked for advice on getting out of a rut. People come to me and say some variant of: I feel like it is time for a change. What should I do next?<br>And I say: Well, what do you want?<br>Rarely does anyone have an answer to this question. It’s not for lack of trying. I don’t know, they say, but I’ve been trying to figure that out. I’ve journaled, I’ve talked to people, I’ve meditated, I’ve thought a lot about it.<br>These efforts have usually driven them in circles, or worse, into the warm glow of some Tik-Toker. Either way, they lose confidence in their own judgment, because none of these activities actually help you develop a clear point of view.<br>The people who have good judgment and a clear sense of what they care about all share one thing:<br>They have...