Ten year plans used to be normal then five year plans took over. Then three years became the horizon most small businesses could actually hold onto.
I don’t think that horizon exists anymore.
The last two years alone have made a three year plan feel more like fiction than strategy. Most agency owners I talk to, myself included, are working off something closer to a one year plan now that is revisited often and held loosely enough to survive contact with reality.
But a plan on its own isn’t enough.
A plan tells you what you already know is working. It won’t tell you what to do with a pattern you’re only half aware you’re noticing, or when to say no to the safe, familiar option in front of you.
The uncomfortable part is what separates a bet from a strategic plan. A plan is usually built on things you already know. A bet requires saying no to the safer, more familiar option in front of you, and choosing the one you can’t fully justify yet.
That discomfort is the point. If it felt safe, it wouldn’t be a bet. It would just be the next obvious step.
A few years ago, my coaching and consulting practice was solid. Steady clients and revenue, nothing broken. The safe move was obvious: keep doing what was already working.
But I kept noticing something underneath the client work.
Agency owners weren’t just asking me for strategy, they were describing something closer to isolation. Nobody in their world really understood what running a small agency felt like day to day, and I saw that pattern surface again and again.
I didn’t have proof that a community built specifically for small agency owners would work. Other agency communities existed and nobody was building it for small agencies. I just had a pattern I trusted and a direction I couldn’t stop thinking about.
So I made the bet. I sized the time I’d give it. I said no to putting that same time into more billable work, which was the safer, more predictable choice.
That became Agency Together.
I see this same shape showing up in the businesses I coach.
An agency owner I work with has two projects going right now that both ask her to advise rather than execute, no design work, no production, just strategic input. Neither one is guaranteed to turn into anything beyond the immediate scope.
We talked through both before she said yes, because when you’re in the middle of a strategic bet, it’s hard to tell the difference between a pattern worth building toward and a distraction that just feels exciting.
Having someone outside it who can look at it objectively is how she knows what to keep and what to drop.
That’s a bet too, built the same way mine was. She can see the pattern clearly, even without proof the direction will pay off, and she’s choosing it over the safer, more familiar version of client work because it’s more aligned with where she wants to go.
That’s the real question heading into next year. Whether you’ve let yourself make a real strategic bet lately, one uncomfortable enough that you had to say no to something safer to make room for it.
I went deeper on what actually separates a strategic bet from a random side project, and how to size one so it can fail without taking your business down. Read more here.
