Why Most Goals Fail — and the Simple Fix That Makes Yours Stick

Most leaders are great at setting goals. We map out the year, the quarter, the month, the week. We look ahead, choose a target, and get excited about where we're going.

But here’s the part almost everyone skips:

Planning for the obstacles.

Not the vague “things might get hard” kind of planning.

The specific, predictable, absolutely-going-to-happen obstacles that your brain will throw at you the moment you start pursuing something meaningful.

Your success doesn’t depend on the goal you set. It depends on whether you’ve prepared for what will try to knock you off course.

A simple example (that you’ve probably lived)

You set a goal:
Work out five days per week. No excuses.

Day 1: Your alarm goes off and you immediately question everything.
Day 4: You’re so sore you walk like a baby deer.
Day 30: You’re traveling and the hotel gym looks like a museum exhibit.

And you tell yourself you don’t need to work out. None of this is a surprise. It’s the human brain doing what it always does: seek comfort, avoid discomfort, conserve energy.

This is why we plan the obstacles on purpose.

Example: Turning obstacles into strategies

Obstacle: I don’t want to get up.

Strategy: Expect this. Remind yourself you made a commitment. Even if you're not at 100%, you still get up.

Obstacle: The hotel gym is prehistoric.

Strategy: Swap the workout: hit a step goal instead of lifting.

Obstacle: I’m too sore.

Strategy: Do yoga or a recovery-focused session.

Obstacle: I stayed up too late.

Strategy: Move the workout to the evening.

This isn’t about perfection. It’s about showing your brain that the excuses are already accounted for — so it can stop negotiating.

Use the same approach at work

Let’s take a goal that feels exciting and challenging:

Double registrations for your customer conference.

You’ll need focus, clean execution, and a team that stays aligned. You’ll also need to anticipate the roadblocks that always show up in any meaningful business goal.

Example: Turning workplace obstacles into strategy

Obstacle: Pre-registration numbers are behind goal.

Strategy: Extend the discount for 5 days, increase targeted promotion, and activate a CS bonus push.

Obstacle: Customers say the cost is too high.

Strategy: Strengthen value messaging for targeted audiences; highlight ROI, outcomes, and social proof so the price feels justified.

Obstacle: Marketing is stretched thin and can’t execute all campaign assets.

Strategy: Prioritize the highest-leverage activities, shift lower-impact tasks to other teams, or temporarily bring in freelance/agency support.

Obstacle: Sales isn’t consistently promoting the event.

Strategy: Provide a simple promo script + one-pager, set weekly targets, and add a short-term incentive to drive follow-through.

The real point

When you expect obstacles, you stop being surprised by them.

You stop letting your brain talk you out of what you committed to.

You become the kind of leader who doesn’t just set goals — you create results.

Ready to make this easier?

I’ve created a simple tool to help you plan your goal, anticipate your obstacles, and build strategies before you need them.

You can download it here — it pairs perfectly with everything we just covered.