All Roads Lead to Home

For over two decades the Chicagoland area was home. I grew up in a northwest suburb, spending most days within a 2 mile radius of my house. When I did venture into the city, I was always with family or on a school trip so we only experienced iconic Chicago:

Michigan Ave., Jordan at the United Center, The Art Institute and Museum Campus, The Willis (read: Sears) Tower, and my Mom’s favorite — Buckingham Fountain. My last event in high school was our post-prom party with views of the skyline from a triple-decker boat off Navy Pier. And to top all those trips, there was a Lou’s across the street from my house.

I was born and raised to love Chicago.

I moved even closer to the city for college, now just a quick L trip away. And every time I went downtown, the picture of what life would be like became clearer: I could rent near (but not in) Wrigleyville. Play pickup volleyball in the summer at North Avenue Beach. Catch the world’s best orchestra every season. Fall in love on the Red line every other week. And Lou’s would still be nearby.

I ran the Chicago Marathon before graduation, and my first thought after crossing the finish line was, “I’m going to retire here.”


Then in early 2011, I landed a gig with a booming startup in California — a dream I didn’t realize I had until I started applying for jobs. Suddenly everything that was familiar seemed easy, and so I told myself what I had to hear to move on:

Zack, you’ll still have an 847 area code.
Zack, the Empire Carpet and LUNA jingles won’t change.
Zack, you’re better off with a challenge away from home.

With 3 suitcases and a carry-on, I moved to Silicon Valley. At the time I had no family or friends within 2,500 miles.

I landed at SFO on a misty, gray day and took a yellow cab to the city. I didn’t have an apartment so I couch surfed across my company for three weeks. It was not easy. My bright blue suitcases stood in the corner of the office where all the fellow new hires could see. On my second night, I sank into a new stranger’s couch, tired, scared and without any leads for an apartment. I curled into a ball and cried.

After three weeks of searching, I moved in with two awesome coworkers who became great friends. Finally, I could focus on work.

ALWAYS BE CLOSING

My main job was building technology to scale our company’s growing sales and service teams. I soon learned the mantra Always Be Closing and the new culture it represented. Regular work happy hours quickly turned into frequent social gatherings. Suddenly I was being invited to dinners, bars, and house parties each weekend. Every executive at my company had witnessed my work ethic, but they’d also seen me tipsy off cheap beer.

Thus I was introduced to work-life in Silicon Valley: the dichotomy of crushing it and cruising; a blur between coworker and comrade.

Sales culture fascinated me especially. Salespeople learn a product, practice pitches, and reach out cold so they can tell you a story. Their work fosters lasting partnerships, solves real business problems, and keeps companies afloat. And they do it dozens to hundreds of times a week. But no matter how much success salespeople can celebrate, their quotas reset at the end of the month or quarter. Each salesperson is a modern day Sisyphus with a cell phone.

Just a standard sales gong

Months passed, and I settled into Silicon Valley life. I loved work, and I loved working. Heading to the office on Saturdays and Sundays was common, and it didn’t feel like work. I was learning faster than ever before, and I respected my team more than anything else. But something didn’t feel right.

Locals would say, “San Francisco is the best city in the world,” and I’d bite my tongue and roll my eyes. Most hadn’t even left Northern California (you could tell because they said “hella” relentlessly). Still, I felt crazy for disagreeing with them. I wasn’t homesick, but my heart wandered. Perhaps I felt guilty for cheating on The Windy City?

Luckily the company’s growth exploded. I was given the opportunity to move back to Chicago to help our remote offices and still travel to California frequently. I didn’t need much convincing this time.

3 suitcases and a carry-on later, I walked into our Chicago office on a Monday morning to open arms.

They’re funny

The sales culture that I loved at HQ had its own blend here in Chicago. Our office was a small family, and I grew to love them as such. Work remained intense, although there were fewer parties with kegs. Remote offices presented their own challenges, but Always Be Closing still rang true.

ALWAYS BE OPENING

After two sublets I moved in with my best friend, an actor and musician. He introduced me to the world of Chicago theater. And surprisingly, here too: the dichotomy of crushing it and cruising; a blur between costar and comrade.

Theatre culture fascinated me. These artists train and rehearse for hundreds of hours so they can tell you a story & get you to feel something. Their work educates kids, makes you laugh, or breaks your damn heart. And they’ll do it 8 times a week (and probably serve your liquor on nights off). Like salespeople, no matter how much success actors can celebrate, their shows eventually close and they must sell themselves again to book the next gig.

I started attending opening night after opening night and meeting brilliantly talented actors, musicians, playwrights, directors, composers — the list went on. It became commonplace that after spending the day building software for a SaaS sales team, I’d come home and spend the night singing and cracking jokes with Chicago creatives.

I had replaced one Sisyphus with another and inspired my inner artist to reawaken. I wrote more. I sang more. I played more. This creative side. This is what I was missing in California.


Then in the summer of 2012, our company was acquired. Chicago was wonderful for me socially, creatively, but professionally being out on my own was hindering my career growth. After four months of internal debate — and a sentimental holiday party at HQ — I made the inevitable decision to move back to San Francisco.

My pro/con criteria used to decide to move (back) to SF

Those closest to me were upset but understood why I was leaving Chicago (again). I needed to do what was best for my career, even if it meant temporarily turning down the volume on my inner artist.

A TALE OF TWO CITIES

Back in SF, I stopped disagreeing with locals when they said, “San Francisco is the best city in the world.” A kid from Menlo Park sees SF the way I see Chicago. And why wouldn’t you?

Both Chicago and San Francisco are havens to creators. Disruptors & directors. Entrepreneurs & entertainers. Programmers & poets.

It’s important to note: both cities have immense work ahead. But hopping back and forth, I’ve learned to appreciate some parallels:

I live with another Chicagoland transplant, a friend from middle school. He’s a salesperson that understands my inner software engineer and inner theater kid alike. Sometimes after reminiscing he’ll ask me: “… so when are you moving back home?” I respond with another question: “Which one?”

ALWAYS BE CREATING

I don’t remember which flight was mine

Last time I was in Chicago I visited the Van Gogh’s Bedrooms exhibit at the Art Institute in Chicago. The three renditions of his bare bedroom represent a mundane but meaningful life in the country, a modest lifestyle with character. A nomad like Van Gogh kept his possessions limited, his appreciation in excess.

What Van Gogh desired most was his own space in which to create — a haven where he could work alongside fellow artists.

I consider myself lucky for having two such spaces. I’m forced to bounce back and forth because my closest friends in Chicago and SF are creative cousins: they connect with audiences on a deeply emotional level by telling stories. They sellsellsell non-stop, even if they’ve hit their quota, even if they’re the star on stage, even if it’s the tenth time they’ve done it this week. They create, and they inspire me to create alongside them.


After being back in San Francisco I regained my bearings. I realized what I had missed the first time and brought my Chicago creator with me. I left my old job, where I was bored and became boring. I gave away nearly everything that didn’t foster creating. And I started a company with fellow creators I respect and admire to help the people we respect and admire.

I’ve spent the last 5 years chasing career, seeking creative asylum, bouncing between two beautiful cities and looking for home. But the truth is all roads lead to home. Not by happenstance but by necessity. We must move to where we find haven. Where we create. Where we can love and feel loved.

For over two decades the Chicagoland area was home. I grew up in a northwest suburb, spending most days within a 2 mile radius of my house. When I did venture into the city, I was always with family or on a school trip so we only experienced iconic Chicago:

Michigan Ave., Jordan at the United Center, The Art Institute and Museum Campus, The Willis (read: Sears) Tower, and my Mom’s favorite — Buckingham Fountain. My last event in high school was our post-prom party with views of the skyline from a triple-decker boat off Navy Pier. And to top all those trips, there was a Lou’s across the street from my house.

I was born and raised to love Chicago.

I moved even closer to the city for college, now just a quick L trip away. And every time I went downtown, the picture of what life would be like became clearer: I could rent near (but not in) Wrigleyville. Play pickup volleyball in the summer at North Avenue Beach. Catch the world’s best orchestra every season. Fall in love on the Red line every other week. And Lou’s would still be nearby.

I ran the Chicago Marathon before graduation, and my first thought after crossing the finish line was, “I’m going to retire here.”


Then in early 2011, I landed a gig with a booming startup in California — a dream I didn’t realize I had until I started applying for jobs. Suddenly everything that was familiar seemed easy, and so I told myself what I had to hear to move on:

Zack, you’ll still have an 847 area code.
Zack, the Empire Carpet and LUNA jingles won’t change.
Zack, you’re better off with a challenge away from home.

With 3 suitcases and a carry-on, I moved to Silicon Valley. At the time I had no family or friends within 2,500 miles.

I landed at SFO on a misty, gray day and took a yellow cab to the city. I didn’t have an apartment so I couch surfed across my company for three weeks. It was not easy. My bright blue suitcases stood in the corner of the office where all the fellow new hires could see. On my second night, I sank into a new stranger’s couch, tired, scared and without any leads for an apartment. I curled into a ball and cried.

After three weeks of searching, I moved in with two awesome coworkers who became great friends. Finally, I could focus on work.

ALWAYS BE CLOSING

My main job was building technology to scale our company’s growing sales and service teams. I soon learned the mantra Always Be Closing and the new culture it represented. Regular work happy hours quickly turned into frequent social gatherings. Suddenly I was being invited to dinners, bars, and house parties each weekend. Every executive at my company had witnessed my work ethic, but they’d also seen me tipsy off cheap beer.

Thus I was introduced to work-life in Silicon Valley: the dichotomy of crushing it and cruising; a blur between coworker and comrade.

Sales culture fascinated me especially. Salespeople learn a product, practice pitches, and reach out cold so they can tell you a story. Their work fosters lasting partnerships, solves real business problems, and keeps companies afloat. And they do it dozens to hundreds of times a week. But no matter how much success salespeople can celebrate, their quotas reset at the end of the month or quarter. Each salesperson is a modern day Sisyphus with a cell phone.

Just a standard sales gong

Months passed, and I settled into Silicon Valley life. I loved work, and I loved working. Heading to the office on Saturdays and Sundays was common, and it didn’t feel like work. I was learning faster than ever before, and I respected my team more than anything else. But something didn’t feel right.

Locals would say, “San Francisco is the best city in the world,” and I’d bite my tongue and roll my eyes. Most hadn’t even left Northern California (you could tell because they said “hella” relentlessly). Still, I felt crazy for disagreeing with them. I wasn’t homesick, but my heart wandered. Perhaps I felt guilty for cheating on The Windy City?

Luckily the company’s growth exploded. I was given the opportunity to move back to Chicago to help our remote offices and still travel to California frequently. I didn’t need much convincing this time.

3 suitcases and a carry-on later, I walked into our Chicago office on a Monday morning to open arms.

They’re funny

The sales culture that I loved at HQ had its own blend here in Chicago. Our office was a small family, and I grew to love them as such. Work remained intense, although there were fewer parties with kegs. Remote offices presented their own challenges, but Always Be Closing still rang true.

ALWAYS BE OPENING

After two sublets I moved in with my best friend, an actor and musician. He introduced me to the world of Chicago theater. And surprisingly, here too: the dichotomy of crushing it and cruising; a blur between costar and comrade.

Theatre culture fascinated me. These artists train and rehearse for hundreds of hours so they can tell you a story & get you to feel something. Their work educates kids, makes you laugh, or breaks your damn heart. And they’ll do it 8 times a week (and probably serve your liquor on nights off). Like salespeople, no matter how much success actors can celebrate, their shows eventually close and they must sell themselves again to book the next gig.

I started attending opening night after opening night and meeting brilliantly talented actors, musicians, playwrights, directors, composers — the list went on. It became commonplace that after spending the day building software for a SaaS sales team, I’d come home and spend the night singing and cracking jokes with Chicago creatives.

I had replaced one Sisyphus with another and inspired my inner artist to reawaken. I wrote more. I sang more. I played more. This creative side. This is what I was missing in California.


Then in the summer of 2012, our company was acquired. Chicago was wonderful for me socially, creatively, but professionally being out on my own was hindering my career growth. After four months of internal debate — and a sentimental holiday party at HQ — I made the inevitable decision to move back to San Francisco.

My pro/con criteria used to decide to move (back) to SF

Those closest to me were upset but understood why I was leaving Chicago (again). I needed to do what was best for my career, even if it meant temporarily turning down the volume on my inner artist.

A TALE OF TWO CITIES

Back in SF, I stopped disagreeing with locals when they said, “San Francisco is the best city in the world.” A kid from Menlo Park sees SF the way I see Chicago. And why wouldn’t you?

Both Chicago and San Francisco are havens to creators. Disruptors & directors. Entrepreneurs & entertainers. Programmers & poets.

It’s important to note: both cities have immense work ahead. But hopping back and forth, I’ve learned to appreciate some parallels:

  • Jordan & The Bulls. Curry & The Warriors.
  • Avoiding Polk Street on Saturday night. Avoiding Wrigleyville always.
  • Curing hangovers with Southport Grocery Brunch. Curing hangovers with Bacon Bacon Breakfast burritos.
  • A morning run by the Bay. A night run by the Lake.
  • A leisure stroll down Michigan Ave. A leisure stroll down Mission St.
  • Celebrating a ProductHunt launch. Celebrating opening night at the Marriott.
  • Subsequently reading the TechCrunch review. Subsequently reading the Tribune review.
  • Reading a poem at The Green Mill on Sunday night. Reading a poem at the corner of 16th and Mission on Thursday night.
  • The SaaS sales culture. The Chicago Theater culture.

I live with another Chicagoland transplant, a friend from middle school. He’s a salesperson that understands my inner software engineer and inner theater kid alike. Sometimes after reminiscing he’ll ask me: “… so when are you moving back home?” I respond with another question: “Which one?”

ALWAYS BE CREATING

I don’t remember which flight was mine

Last time I was in Chicago I visited the Van Gogh’s Bedrooms exhibit at the Art Institute in Chicago. The three renditions of his bare bedroom represent a mundane but meaningful life in the country, a modest lifestyle with character. A nomad like Van Gogh kept his possessions limited, his appreciation in excess.

What Van Gogh desired most was his own space in which to create — a haven where he could work alongside fellow artists.

I consider myself lucky for having two such spaces. I’m forced to bounce back and forth because my closest friends in Chicago and SF are creative cousins: they connect with audiences on a deeply emotional level by telling stories. They sellsellsell non-stop, even if they’ve hit their quota, even if they’re the star on stage, even if it’s the tenth time they’ve done it this week. They create, and they inspire me to create alongside them.


After being back in San Francisco I regained my bearings. I realized what I had missed the first time and brought my Chicago creator with me. I left my old job, where I was bored and became boring. I gave away nearly everything that didn’t foster creating. And I started a company with fellow creators I respect and admire to help the people we respect and admire.

I’ve spent the last 5 years chasing career, seeking creative asylum, bouncing between two beautiful cities and looking for home. But the truth is all roads lead to home. Not by happenstance but by necessity. We must move to where we find haven. Where we create. Where we can love and feel loved.