Work Backwards - #22

Destination is determined by direction, not intention.

First, Happy New Year. I hope you’re off and running on your 2026 goals.

That said, this newsletter may throw a small wrench in your plan.

Every year, most of us sit down and set goals. Some do it thoughtfully. Others do it quickly. But after reflecting on the process, I’ve realized that many people aren’t failing to keep their goals because they lack discipline or motivation, they’re failing because they’re setting goals that don’t fully align with what they are looking to get out of life.

We tend to start with the near-term:

• Make X dollars this year

• Lose or gain X pounds

• Get the promotion

Those goals aren’t wrong. But they’re incomplete.

The more important question is this: What’s the ultimate goal, and do these goals actually move you closer to it?

When you look back on your life, will these achievements matter? Or were they just milestones that kept you busy?

High, Hard Goals Aren’t Far Enough Out

High, hard goals are meant to be moonshots, beyond stretch goals, beyond comfort. But even those often aren’t far enough out to force real clarity.

Ask yourself: If you double, triple, or even 10x, your income this year, does that actually get you closer to a life you’d consider a success when it’s all said and done?

That’s an uncomfortable question, but it’s the right one.

This requires a somewhat grim exercise: Imagine the last day of your life. What do you want to look back on and know you did well? Who did you show up for? What did you build? What mattered?

Once that picture is clear, work backwards. From that endpoint, determine the steps required to get there.

You may realize that some of the goals you’re setting today don’t actually move you closer to that final outcome at all. They’re just motion.

Beware the Course Creep

Two examples illustrate how easy it is to drift.

First, aviation. A pilot who’s just one degree off course will end up roughly 20 miles off target over a 1,000-mile flight. One degree. Barely noticeable in the moment, but massive over time.

Second, a recent viral trend with AI. People asked AI to recreate an image and “change nothing,” then repeat the process 100 times. Each iteration looks almost identical to the last, but by the end, the image is completely unrecognizable.

No big mistakes. No dramatic shifts. Just tiny deviations without course correction.

That’s how people end up far from where they intended to be. Not through bad decisions, but through slightly misaligned steps repeated over time.

Direction matters more than effort.

Rebuild the Goals

With this in mind, it’s time to rebuild.

Start with the end. Define what success actually means to you, not socially, not professionally, but personally.

Then rebuild your goals so they align with that destination.

Finally, make sure you keep that end goal in mind to stay on course.

When goals are rooted in purpose, they carry weight. They’re harder to abandon. And they’re far more likely to lead you somewhere meaningful.

Final Thought

Goals matter. But why you’re chasing them matters more.

Don’t set hollow goals that look good on paper but create no real value in your life.

Decide where you’re going. Then work backwards, and adjust often to stay on course.

Additional Resources

• Book: Four Thousand Weeks by Oliver Burkeman – Buy here

• A reminder that time is finite, and direction matters more than optimization.

• Podcast: The Knowledge Project – James Clear: How to Build Good Habits & Break Bad Ones – Listen here

• Stoic Quote of the Month: “If one does not know to which port one is sailing, no wind is favorable.” — Seneca

• Effort without direction is just drift.