Be yourself đ
Enter the judgment-free zone, where career crossroads, impostor syndrome, and crises of faith donât mean the sky is falling
Hi there! Youâre reading the Bonfire newsletter from Kevan Lee & Shannon Deep. Each week, we highlight brand, marketing, and creative learnings from our experience as in-house marketers turned agency owners who think a lot about creativity, our relationship to work, and how all of that impacts our identities. Weâll also feature insights from our digital community of super smart folks (which youâre welcome to join).
Wishing you a great week!
The heart wants what the heart wants
One of the go-to Zoom questions on new calls is the classic, âWhere are you calling from?â And my answerâBoise, Idaho, USAâelicits one of several responses:
Huh?
Polite blinking, followed by quick subject-changing
Praise for the natural beauty of Idaho and the abundance of outdoor activities
Stories about that one time they drove through Boise on their way to somewhere else
Boise is a five-hour drive from Salt Lake City, Utah; it is seven-and-a-half hours to Seattle, Washington, and it is 10-plus hours from San Francisco. We have a cute little airport that requires multiple stops to get to most places of note. Famously, our internet goes out when bears use cell towers as scratching posts.
So needless to say, I did not grow up ensconced in Silicon Valley culture. I am an outsider, posing as an insider, and I spent pretty much my entire career faking it til I made it. When I got my first startup job, I had to look up the definition of MRR.
This outsider status led to some pretty intense impostor syndrome and a persistent case of the âshoulds.â I am still working to overcome both, plus my other ills. The voices in my head stay the same, and their focus has merely shifted from my in-house work to my Bonfire work.
Impostor syndrome: I donât know enough about how to run a successful business. I am no [insert Silicon Valley founder here]!
Shoulds: I should post more on social media, I should be more interested in networking, I should listen to a business podcast for once in my life.
Comparison: Everyone else seems to have their life figured out.
Groupthink: Climbing the corporate ladder is just what people do. Donât be silly.
Fear: What if it all goes wrong?
Mythbusting our toxic thoughts
I was talking to a friend the other day about a decision they made to quit the rat race of tech startups and to instead find a job that ended at a decent hour and left them plenty of time to invest in their hobbies and their family. That doesnât sound like asking too much, right? And yet the decision was weighty. It was hard because so much of this personâs work context has been shaped by the stories that surround us.
How can we unlearn those stories and feel more confident in choosing our own paths?
I am a work in progress, but the thoughts I struggle with most often tend to be assuaged by mindfulness and reflection. Here are some of my favorite thought starters and prompts for silencing the voices in my head.
Impostor Syndrome
That sneaky feeling that you donât know what youâre doing, that everyone else is more legit than you, and that youâre only one mistake away from being found out. One of our most-loved newsletter posts ever was written on this topic.
Prompts:
Whatâs something Iâve learned on the job that Iâm proud of?
What would I do differently if I trusted that Iâm capable?
What would I tell a friend who felt the way I do?
For me, I am guilty of being far kinder to others than I am to myself, and knowing that this extends to my impostor syndrome helps me balance out reality from fiction. I think others are pretty great, even if I doubt myself; others probably think Iâm pretty great (this is WILD to me, some days), so maybe I can try to see what they see in me.
The Shoulds
The endless to-do list of behaviors youâre supposed to adopt to be seen as ambitious, professional, or âgoodâ at your job. And yes, weâve written about this before, too.
Prompts:
Who decided I should want this?
What âshouldâ can I let go of this week?
What do I want instead?
For me: Iâve started turning my âshouldâ into âcould.â Rather than, âI should post more to social media,â Iâve reframed it to âI could post more on social media.â What a relief!
(Thank you to Kira Klass for the should/could recommendation.)
Comparison
Measuring your worth against other peopleâs LinkedIn announcements, highlight reels, or career timelinesâand coming up short.
Prompts:
Whose career am I comparing mine to, and why?
Whatâs something Iâve done that the younger version of me would be thrilled about?
What might my path look like if I didnât need to explain or justify it to anyone?
Groupthink
The pressure to follow the conventional path because itâs what everyone else is doingâeven if it doesnât feel right for you.
Prompts:
If no one I knew was in this job, would I still want it?
Whatâs a time I made an unconventional choice that paid off?
Where am I following a script I didnât write?
For me, itâs helpful to talk to people outside my bubble, especially people outside of tech, to better understand just how narrow some of my beliefs about myself, the work world, and the career ladder truly are. Go figure: Most people donât know the difference between a Head Of and a Vice President.
Fear
The gut punch of âwhat if it all goes wrong?â that makes any dream feel too risky to even consider.
Prompts:
Whatâs the worst-case scenarioâand what would I do if it happened?
Whatâs the best-case scenario Iâm not allowing myself to imagine?
What would I try if failure didnât count against me?
So, what if you want to do things your own way?
All these toxic thoughts might lead you to believe: Itâs easier to just stay where you are.
The status quo is safe.
Why rock the boat?
Inertia can be an incredibly strong force when it comes to determining how we design our careers. A lot of people stay in the same jobs they started in, never questioning any other paths (plenty of people stay somewhere because they love the job, too, and good for them finding a forever home). In fact, we have so many forces working against us when it comes to thinking differently about work: social media signaling, burnout and overwork, opaque hiring processes, poor job markets, and the list could go on and on. The capitalist machine doesnât really want us cogs questioning whether itâs worth it to remain a cog. The machine reinforces cog behavior in all sorts of different ways, whether itâs through remuneration, status, or peer pressure.
This is why our toxic thoughts can feel so toxic. The system benefits from toxicity. It keeps people where they are.
So when it comes to designing a career of your choice, the key is to keep reminding yourself that you do have a choice. For many years, I forgot this! Sure, perhaps my stifled inner voice might have said that I did in fact enjoy striving toward a VP title at a fast-growing startup; but I stayed on the treadmill without really wondering. I didnât know that people could wonder, were allowed to wonder.
Bless those of you who have given it some thought and intentionally have chosen a path for yourself. Youâre several steps ahead of where I was!
For me, it was a two-step process:
Figure out what you want to be doing
Recognize what you need in order to make it happen
(Step zero: give yourself permission and time and space to figure stuff out!)
For some of you, with step one, the thing you want to be doing will be the thing you are doing right now. Congrats! For step two, you may just need to figure out how to keep doing your work while, say, managing up to a difficult boss or navigating a yucky work culture or setting work-life boundaries.
For others, the step of figuring out what you want might take you in a totally new direction. Also congrats! You are brave and capable and will go on and do great things. In order to make this new path happen, you have a bit more resistance, not the least of which are the toxic thoughts and cultural pressure working against you.
Over to you
Have you spent time thinking about what you really want for your career? Howâs it going? Which of the voices do you have in your head, and how do you deal with them?
Let us know. Weâd love to hear from you!
Want more like this? Join us in Campout.
In Campout, our digital community, we talk about stuff like this on the daily in our channels and a couple times a month in our live events. All supported by exercises and templates to help you craft a career with purpose and intention.
Next month, join us for:
DIY Sabbatical: Design your own recharge. A working session that answers the question: What if you could design a mini-reset that fits your actual life, not the version where you have unlimited PTO and zero responsibilities?
Career AMA (Save the Date). Our very first Career AMA is in the worksâwhere someone gets real about their career journey, the pivots, the wins, the "wait, how did I end up here?" moments, and everything in between.
But wait! Thereâs moreâŚ
Wanna hang out?
Weâre SOLD OUT for our first retreat this fall, but you can join the waitlist for our next one, coming spring of 2026.
Wanna be friends?
If you love this newsletter and wish it were more interactive, youâre in luck! Join us over in Campout, our digital community for creative marketers and the creative curious.
Wanna work with us?
If you need help with brand strategy and storytelling, fractional brand and marketing leadership, and bringing your brand strategy to life in impactful ways, send us an email at hello@aroundthebonfire.com to get in touch.
As always, you can find us on LinkedIn, Instagram, and Threads.