Hi there! You’re 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. We’ll also feature insights from our digital community of super smart folks (which you’re welcome to join).
Wishing you a great week!
How to plan your future, your way
When I was in my early twenties, trying to figure out life, I turned to my parents for advice because I really admired the life that they had built. Specifically, I wanted to know how they planned ahead and set goals for where they wanted to be in three, five, ten years.
Their answer: They never set a single goal, much less had a five-year plan.
I was aghast.
My very accomplished parents were more chill about the future than 20-year-old me had ever been. What gives.
Fast forward to the early days of my startup career, and I was again in my feelings about the future. I was sweating over my five-year plan, clearly having taken none of my parents’ advice about goal-setting. In a 1:1 with my manager, we began talking about career development, and I admitted that I did not have a crystal clear picture of what I wanted. Turns out, I was not alone. I was normal even! Not everyone has life figured out, to my surprise. We talked through two very common perspectives on the five-year plan:
Roadmaps. In this perspective, you have a clear idea of where you want to get and the directions on how to get there. You are Mapquesting your way through life.
Lilypads. In this perspective, you hop from lilypad to lilypad when and as you see fit. There is no single, “right” path through the lilypads, and you can traverse at whatever pace and in whatever direction you want.
The five-year plan was a spectrum: Mapquest on one side, froggies on the other.
Fast forward one last time to our fall Bonfire retreat, which we just wrapped up (much more detail to come on this; stay tuned!). As part of our programming, in a session led by Rachel Korb from
, we invited people to hop into a time machine and journey three years into the future to observe the life they’ve built. People had very different experiences of this exercise. For some it was easy to imagine three years ahead; for others it was difficult. Some people had clear milestones they hoped to reach, while others were more obscure with details but clear on how they wanted life to feel in three years.Turns out, there is no “right” way to dream.
Sorry to my parents for how much grief I gave them back in the day!
Why do we feel like we need a five-year plan?
Clearly I felt (and still feel) a lot of pressure to have a plan. Without a plan, 20-year-old me felt like I was doing something wrong with my life, missing out on a better future because I was procrastinating on my Nintendo 64 when I could have been making vision boards. The pressure is real, but it’s also a result of the society in which we live. There’s nothing wrong with having a five-year plan; the problem begins when we presume that a five-year plan is the only way to go, the one right answer to solve everything. Life is a little more nuanced than that, but you’d be forgiven for thinking otherwise.
Here’s what we’re dealing with:
Capitalism loves a roadmap. We’re conditioned to think in timelines and linear growth through our jobs every single day. If something as inert as software can have a one-year OKR roadmap, then surely I can (should!) come up with a yearly set of goals for myself. Capitalism rewards efforts to become more efficient and more goal-oriented because the pursuit of these goals reinforces key ideas about insufficiency, which motivates people to work harder and spend more in the pursuit of being whole.
Comparison is an effective motivator but a terrible analyst. It’s incredibly tempting to see other people’s success and then to build goals for ourselves to “keep up with the Joneses.” The problem: We have no idea what it took for the Joneses to get where they are. I have been guilty of building career roadmaps to keep me on track with my peers, albeit having zero context on how my peers got where they got: Were they lilypad-hopping carefree up the corporate ladder? Did they catch a lucky break? Did they grind for 10 years in an MBA program? Is their dad the CEO? No matter. We see success on LinkedIn, and we are tempted to keep up.
We are worse off than our parents. Millennials are the first generation to be worse off financially than the generation before. Those are some big odds stacked against us, so it’s no wonder that we can be inclined to build plans to mitigate the macro regression of our generation. The thinking: Maybe a five-year plan will help us be an outlier from the otherwise wrecked curve.
Mediocrity is a dirty word. In a very tangible way, mediocrity is punished in tech by businesses failing, GTM leaders getting ousted, and boardrooms getting super angry. I get the shakes thinking back to the “code red” moments at work when revenue was anything other than hypergrowth. Static growth is mediocre, and mediocrity is unacceptable. The solution, of course, was to plan and hustle your way out of the mediocrity mire. There’s nothing a well-articulated goal can’t fix.
All these points speak to the tricky world in which we live, and also when society isn’t working against us, then science is: Our nervous systems crave security, and having clear plans for where we’re headed goes a long way to soothe our lizard brains.
But all hope is not lost!
It might sound like I want to send goals straight to jail, but I do find goals and plans to be quite valuable. They’ve gotten me really far in life, and they’ve helped focus our Bonfire business in a way that’s allowed us to achieve great things. Rather than toss plans completely out the window, I think it’s important that we look to the future according to a timeline and process that is unique to each of us. No all-or-nothing five-year planning cycles. Rather, we can find peace and progress by planning ahead in a more personal way.
Find the right time horizon for YOU
Just like with creativity, you need the right conditions in order to dream of the future. You need safety, stability, and self-trust to imagine a future worth getting excited about. Some seasons of life support that more than others. So instead of defaulting to “five years,” try asking: What time horizon feels generous right now?
When a 6-month time horizon might make sense
There have been many seasons of life when six months felt like an eternity to me. Six months from right now is April 2026. Is that even a real date?!?!
Not only is everyone wired differently but also our comfort level with planning can shift from season to season. Six month goals feel more comfortable and reasonable when you are navigating a lot of personal change and feel unsure where things will land. Six month goals are appealing for people who thrive on spontaneity and require flexibility.
In particular, six-month time horizons might be useful for:
Hopes and dreams at a new job
Business planning for a baby business
Life goals fresh out of school, after a big move, or following a big relationship change (starting or ending)
When a 1-year time horizon might make sense
A year is enough time to try something, pivot if needed, and still feel like you’re making progress. It gives structure without locking you in. And importantly, it often lines up with how the world works — performance reviews, school years, funding cycles, resolutions. No doubt you’ll be inundated with New Year’s resolution content soon enough, which makes for a natural 1-year planning ritual.
A 1-year time horizon is especially great when you have some clarity but still want room to experiment. It’s helpful for setting intentions that stretch you, but don’t overwhelm.
Some good fits for a 1-year plan:
Career growth, specifically with adding a new skill or aiming for a promotion (and in this job market, it might require a 1-year plan to find a new job)
Building habits, i.e. health, creativity, consistency
Setting the pace for a side project or passion pursuit
When a 3-year time horizon might make sense
This is the sweet spot for visioning. Three years is close enough to feel real but far enough that you’re not bogged down in logistics. It’s often where people naturally dream — not what happens next, but what could happen if.
Three-year plans are especially helpful when you’re feeling grounded, curious, and ready to stretch. You don’t need to know every step — just a general direction.
Three-year thinking works well for:
Mapping the future of a business or career shift
Aligning your life with your values (more space, more autonomy, more joy)
Imagining how you want to feel and designing from there
When a 5-year plan might work
Five years is legacy-building territory. So the key here is not precision; it’s permission. When you feel safe and resourced enough to imagine a longer arc, a five-year plan can be a powerful thing. This kind of visioning often shows up when you’ve got a strong sense of self, a clear desire, and the capacity to move toward it, step by step. Think back to the foundations we mentioned at the start: You need safety, stability, and self-trust to really feel good about dreaming ahead five years into the future.
You might be ready for a five-year plan if:
You’re building something long-term (a business, a family, a creative body of work)
You have a strong inner compass, even if the path isn’t linear
You’re craving stability, structure, and deep investment in what matters most
Your future, your framework
The most honest planning often starts with how you want to feel, not just what you want to achieve. We saw this firsthand during the retreat. If you’re struggling to imagine specific outcomes you want in one, three, or five years, maybe you’re more inclined to dreaming about how you want life to feel. If you’re very detail-focused, then perhaps you can benefit from reflecting on how you want life to feel when you’ve achieved all that you’re setting out to achieve.
Regardless of your planning perspective, just know that everyone plans differently and that your plans for the future need not look any more robust than what feels right for you right now.
Just ask my parents!
Upcoming Campout events
Join our Campout community to
DIY Sabbatical: Design your own recharge.
This Wednesday, October 15, at noon Eastern
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 w/ Allison Stadd.
Wednesday, October 29, at noon Eastern
Our very first Career AMA features Allison Stadd, CMO at Ollie and former marketing and brand leader at Shipt, Shake Shack, Sweetgreen, and more. This event is FREE to anyone and everyone. Tell your friends!
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.
But wait! There’s more…
Wanna hang out in person?
New retreat dates are coming soon. 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, you’re 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.
