Yesterday, I broke in a new pair of kitten heels. They were a perfect color for early fall, nude with a touch of faux snakeskin for texture, an ideal complement to my floral pants and orange sweater. But by the time I reached the office, the pain in my heels was unbearable. I spent the first 30 minutes of my workday doing emergency first aid on my feet. I bought socks and went shoeless at my coworking space all morning to recover.

By lunch, I knew I wouldn’t last through the day, let alone happy hour. So, I headed to DSW at Union Square, with one clear goal: find more comfortable shoes that still matched my outfit, and ideally, a pair I could wear again.

The second floor was a palatial showroom of 1,000 shoes—flats in one corner, sneakers in another. Boots lined the middle, with dainty heels dotting the edges. As I browsed, I realized there were at least 20 pairs that would fit. Sandals to avoid friction, backless wedges for fall, or boots to cover my bandaged feet. The possibilities were overwhelming. 

I asked myself: What are you looking for?

I ask this question nearly every day of the week, to job-seekers in my personal and professional network. What I’ve noticed is, this is a really hard question to answer.

I tend to get a lot of varieties of response:

• “More autonomy.”

• “More money.”

• “More flexibility.”

• “More mentorship”

• “Less micromanaging.”

• “Less stress.”

• “Less travel.”

• “Honestly, I don’t really know. I just want something different.” 

This last one is the most common. I get it. But, much like a shopkeeper trying to help you find the right pair of shoes, it doesn’t provide enough direction to narrow down your options.

In a way, searching for a new job feels a lot like shopping for shoes. There are countless options—companies, careers, and directions that could fit. But the sheer number of possibilities can make it hard to know where to start. This feeling is compounded by the societal pressure to find one “right” answer, as though a career is a train track or a ladder heading in a single direction.

Instead of seeing your job as a singular career path, why not think of it as the pair of shoes you need right now?

I wandered through DSW in my socks, heels dangling in one hand, slipping on shoes and wincing as each one further irritated my feet. It became clear I needed something with soft, flexible fabric to avoid more pain. I passed on ballet flats that weren’t in my size, clogs with rigid seams, but refused to ruin my outfit by opting for running shoes. 

After one full lap around the store, I had only one contender: A brown wedge with an open back. Not my usual style, but you know, desperate times.

On my way to the register, I spotted one last pair of loafers and tried them on. They were surprisingly comfy and complemented my outfit perfectly. At the register, the name popped up on the screen, and I had to double-check.

“Wait, what’s the name of these shoes?”

The shopkeeper checked. “They’re called the Bethany Loafer.”

“Oh my god.”

“What? Is Bethany your name or something?”

“Yes.”

We both doubled over in laughter. She insisted that I keep the box.

If you’d asked me, “What’s your dream shoe?” yesterday, it wouldn’t have helped me make a smarter decision at the DSW. I would have described something far-fetched and fantastical, like a mid-heel with flower vine straps. But what I really needed yesterday was a functional, comfortable shoe to walk in.

Rather than seeing your job as a single, linear path, think of it like shopping for shoes. There are many pairs that will fit your feet...er, career goals. You can wear one pair for a season, another for a night, or stick with your favorite sneakers until they fall apart—then get a new pair and do it all over again.

The nice thing about shoes? Your size doesn’t change much. You can always keep them in your closet, ready to wear again. Jobs are the same. Don’t stress so much. Just find the pair you need right now. Who knows, maybe your name is already written on the box.

Yesterday, I broke in a new pair of kitten heels. They were a perfect color for early fall, nude with a touch of faux snakeskin for texture, an ideal complement to my floral pants and orange sweater. But by the time I reached the office, the pain in my heels was unbearable. I spent the first 30 minutes of my workday doing emergency first aid on my feet. I bought socks and went shoeless at my coworking space all morning to recover.

By lunch, I knew I wouldn’t last through the day, let alone happy hour. So, I headed to DSW at Union Square, with one clear goal: find more comfortable shoes that still matched my outfit, and ideally, a pair I could wear again.

The second floor was a palatial showroom of 1,000 shoes—flats in one corner, sneakers in another. Boots lined the middle, with dainty heels dotting the edges. As I browsed, I realized there were at least 20 pairs that would fit. Sandals to avoid friction, backless wedges for fall, or boots to cover my bandaged feet. The possibilities were overwhelming. 

I asked myself: What are you looking for?

I ask this question nearly every day of the week, to job-seekers in my personal and professional network. What I’ve noticed is, this is a really hard question to answer.

I tend to get a lot of varieties of response:

• “More autonomy.”

• “More money.”

• “More flexibility.”

• “More mentorship”

• “Less micromanaging.”

• “Less stress.”

• “Less travel.”

• “Honestly, I don’t really know. I just want something different.” 

This last one is the most common. I get it. But, much like a shopkeeper trying to help you find the right pair of shoes, it doesn’t provide enough direction to narrow down your options.

In a way, searching for a new job feels a lot like shopping for shoes. There are countless options—companies, careers, and directions that could fit. But the sheer number of possibilities can make it hard to know where to start. This feeling is compounded by the societal pressure to find one “right” answer, as though a career is a train track or a ladder heading in a single direction.

Instead of seeing your job as a singular career path, why not think of it as the pair of shoes you need right now?

I wandered through DSW in my socks, heels dangling in one hand, slipping on shoes and wincing as each one further irritated my feet. It became clear I needed something with soft, flexible fabric to avoid more pain. I passed on ballet flats that weren’t in my size, clogs with rigid seams, but refused to ruin my outfit by opting for running shoes. 

After one full lap around the store, I had only one contender: A brown wedge with an open back. Not my usual style, but you know, desperate times.

On my way to the register, I spotted one last pair of loafers and tried them on. They were surprisingly comfy and complemented my outfit perfectly. At the register, the name popped up on the screen, and I had to double-check.

“Wait, what’s the name of these shoes?”

The shopkeeper checked. “They’re called the Bethany Loafer.”

“Oh my god.”

“What? Is Bethany your name or something?”

“Yes.”

We both doubled over in laughter. She insisted that I keep the box.

If you’d asked me, “What’s your dream shoe?” yesterday, it wouldn’t have helped me make a smarter decision at the DSW. I would have described something far-fetched and fantastical, like a mid-heel with flower vine straps. But what I really needed yesterday was a functional, comfortable shoe to walk in.

Rather than seeing your job as a single, linear path, think of it like shopping for shoes. There are many pairs that will fit your feet...er, career goals. You can wear one pair for a season, another for a night, or stick with your favorite sneakers until they fall apart—then get a new pair and do it all over again.

The nice thing about shoes? Your size doesn’t change much. You can always keep them in your closet, ready to wear again. Jobs are the same. Don’t stress so much. Just find the pair you need right now. Who knows, maybe your name is already written on the box.