The middle is where strategy goes to die

I've sat in enough rooms where a team needs to make a big strategic call and instead of choosing a direction, they try to take a little from both sides. It feels smart. Balanced. Low risk. Then six months later the business is slower, more complex, not achieving the results you'd expected, and nobody can explain why.

A committed strategy collects all the pros. A middle-of-the-road strategy collects all the cons.

I come back to this all the time.

Commitment is what unlocks the upside

Every strategic direction has trade-offs baked in. Real pros and real cons.

The pros only show up when you commit. You have to go deep enough for it to actually work, because the cons are there from day one no matter what.

When you go all-in, you pay the cons once and stack the pros over time. You build systems around the hard parts and get good at managing them.

When you hedge and play the middle, you pick up the cons of both directions without going deep enough in either to see the upside. You end up with the worst of both worlds and nobody realizes it because it felt like the safe choice.

I've lived this many times. There are countless examples where I've been a part of teams who have made this mistake, but one that sticks out is when we were looking to move from DTC into retail. We built the business on DTC, but growth pressure started building and so the logical next step was channel expansion. On the surface it sounded like we could have it both ways. Keep our DTC playbook, keep doing high-low pricing, skip building out a real assortment, and just start selling into stores. In reality we'd be taking on all the operational weight of retail without giving it what it actually needs to work. Plus, we'd be pulling focus from DTC without getting any of the real upside of being in stores.

After fumbling around in the middle for too long, we finally landed somewhere that worked, but we collected all the cons and none of the pros for a while. This concept of aggregating pros or cons is front of mind for me because I've felt the drag firsthand.

The real work

Choosing a direction is the easy part. Most people get stuck when they have to be honest about what that choice actually costs them and then commit to the direction. We don't like naming what we're giving up. So we try to engineer around the cons. We hedge. And that's how we end up in the mushy middle.

Good strategy is "here are the pros we're collecting" followed by "and here are the cons we're okay with." Both specific. Both written down. If you can't do that, you haven't actually made a decision yet.

The best strategies feel lopsided from the outside. People will ask "but what about X?" and the answer is "we know about X. We accept X because it's the price of Y and Z, which is where we win." When your team has that clarity, they make faster calls on their own. They know what to optimize for. Hedging kills that. When the strategy is "a little of everything," every person prioritizes something different and nobody builds real depth anywhere.

There are always downsides. You just need to know what they are going in and decide they're worth it. Most teams never get that far.

P.S. If your team can't name the cons they've accepted, you shouldn't move forward with the strategy.