CJC Interview: Jesse Hagen, Content Director


“In my career, I want to continue collaborating with people who make me better and expose me to the unfamiliar." 

“In my career, I want to continue collaborating with people who make me better and expose me to the unfamiliar." 

Where do you hail from/live currently? “Rochester, Minnesota; Queens, NY.”

Where do you find inspiration? “My 13-month-old son’s fascination with the world is the best re-energizer when books, music, and films aren’t cutting it.”

How would you describe your personality? “At my best, I think I’m pretty good at supplying memorable moments or funny stories to any conversation. The nicest thing anybody ever said after meeting me was “he makes you feel like you’ve been great friends for years.” That meant a lot to me and I try to exemplify that (I never thanked you for that, @beware4).”

What does being an ‘entrepreneur’ mean to you? “Being an entrepreneur to me means pursuing and planning projects that ignite the fire of your soul, which may exist outside the confines of previously-existing organizations.”

What’s the biggest misconception you face re: WFH? “For me it’s that it’s all recreational all the time. The trappings of WFH can be liberating (sleeping in, setting your own schedule, etc.), but to be productive, you also have to be enormously disciplined. It’s hard when a plethora of recreational fun and domestic needs beckon when you’re bogged down with the less-fun logistics of a project.”

Who was the last person that inspired you and why? “My friend Luke, who I recently had a beer with. He speaks something like 6 languages, and I’m always grateful to witness how different his mind works from mine whenever we catch up.”

What’s your favorite ‘me-time’ or ‘self-care’ activity? “I enjoy crosswords and devouring novels.”

What is the biggest lesson you learned in your 20s? “When it comes to career: knowing when it’s time to forsake stability for passion and principles. When it comes to me: being content with being unable to please everybody, including myself.”

What is your outlook on your future career? Your career industry? “In my career, I want to continue collaborating with people who make me better and expose me to the unfamiliar.  As far as writing or content creation goes, I’m sometimes discouraged by how disposable the work is treated, a regrettable byproduct of the continuous  deluge we’re exposed to on the internet. I hope publishers and networks create mechanisms better designed to preserve the shelf life of slow-burn work that sacrifices a viral angle in favor of being layered, complex, and worthy of repeated reads, views and listens.”

Would you ever go back to a corporate career? “I feel unqualified to be answering these questions because I recently did! That said, I’ve always tried to keep my entrepreneurial spirit kindled whenever I take on a full-time job, whether through side projects (I co-penned a webcomic during my previous job) or trying to expand the definition of my job description in unexpected ways.”

What’s your favorite quote?  “During a lecture, an Oxford linguistic professor noted that while English had several instances of a double-negative connoting a positive, there was no language he knew of in which a double-positive connoted a negative. In a thick Brooklyn accent, Sidney Morgenbesser sarcastically piped up from the back of the room, “Yeah, Yeah.””

What is the biggest contributor to your personal, inevitable self-doubt? “Not measuring up to my heroes. Not being as accomplished as I hoped I’d be at my age.”

If you could give one piece of career advice what would it be?  “Losing a job is like a forest fire. The blaze feels all-destructive in the moment, but the flames also refertilize the soil, preparing it for regrowth.”

Who do you find in business, a personal mentor or celebrity figure to be most intriguing? “I have a lot of  admiration for my mentor and friend Woodie Wentworth (IG: @woodiemoon), who I find to be singularly talented in every project she does, particularly her latest, 24/7 Perspective. John Gotty (IG: @johngotty), the first person who ever took a chance on my writing, is another one. He continues to innovate and evolve in novel ways no matter the channel. His “The 5” stories on Instagram is the cleanest use of the feature I’ve seen. Uncomplicated. Direct. Contemplative.”

If you weren’t pursuing your current career, what would you want to be doing? “Probably some romantic pursuit that isn’t as fun as it is in my imagination, like working on a fishing boat. I remember driving from MN to NY for the first time thinking it was going to be some Kerouac-esque journey of enlightenment, only to discover miles of gray superhighway.”

If you could give younger self any piece of advice what would it be? “Be more succinct (still applies).”

How do you define success? “Eliciting  laughter, joy, discovery, nostalgia, or intrigue in a manner that sticks with people.”

What are your greatest strengths/weaknesses as an entrepreneur and/or WFH? “I’m a dreadful procrastinator and a middling self-editor with too little patience. I’m sour and resentful (probably a little vindictive too) when it happens, but I’m honestly much better when someone deigns to question and challenge my work.”

What do you believe most prepared/inspired you to work solo—i.e. corporate experience, college, friends, family, etc.? “Starting to write with a collective of sharp people who were blazing their own paths in my senior year of high school definitely fueled my independent streak. It endures because those people continue to accomplish such captivating and impressive things.”

What is your favorite Instagram to follow? Favorite brands on social? “Of the people I haven’t shouted out, I’m biased but justified in my appreciation for @ben_vogel, who exhibits a very keen and clever eye. I love how he deconstructs and reconstructs image fragments to render something fresh and unexpected.”

What’s something few people know about you? “I delivered pizzas for a spell. Interesting work.”

The Crackerjack Collective is a series of informal interviews for These New Walls, featuring my entrepreneur and/or work from home network that continuously inspires me. These interviews are meant to, in turn, inspire others looking for similar insight on what we do and the motivation to get started. x Kate, Founder, TNW