7 Questions to Ask If You’re Failing One Success at a Time

Are your small successes actually leading you to failure?

One of the more frustrating things about life, work, and business is how easy it is to look back over what you’ve been doing to see that you’ve done a lot but don’t seem to have pushed the ball forward on any major priority. Sometimes we look back and see that we’ve been spinning our wheels, which is itself frustrating, but an even more insidious pattern is when we look back over a string of successes that don’t tie together into a fundamental win.

What makes the pattern of succeeding without getting anywhere so insidious and challenging is that it’s hard not to celebrate the small win when you have something to show for it — it’s not as if you were just sitting there — so it creates a self-reinforcing pattern because of the feedback loop that’s created. Since we all love winning and are praised for doing it, we use the same way of thinking, doing, and being to create more small wins that we get praised for. Conversely, doing something different means potentially failing. If it ain’t broke, don’t fix it, right?

But what can happen is that we end up chasing smaller, more comfortable, and shorter-term wins than we could otherwise pursue if we paused and thought about what we were really out to do and what our biggest impact could be. Our nets end up filled with small fish we have to go out and catch day in and day out rather than the big fish that could sustain us for weeks or months. Sometimes we do this because we believe that someday we’ll be able to go out into the deeper waters, but we don’t have the time, energy, and know-how to get there. Other times, though, we don’t venture into those deeper waters because we don’t believe we can, or we don’t even know they’re out there — we’re stuck in our known world. The known world keeps us fed and safe, after all.

Small Wins Don’t Always Add Up

Before I go on, there’s nothing wrong with staying in the shallow waters if that’s what best serves your individual and inter-related matrix of needs and priorities. If you’ve just learned that you’ll be a parent soon or that one of your parents has come to need additional care, you may not have the bandwidth or interest in going out into those deeper waters. Or, better stated, those projects are going to be your deep water fishing — you don’t need to stack on others. (Remember, if it takes time, energy, and attention, it’s a project.)

But, all too often, when we look back, we see that we’ve in fact been failing one success at a time because those strings of small wins don’t add up to the transformative change or impact that being more focused, patient, tenacious, and strategic with one bigger project would’ve done. While this may seem really abstract, you’ve no doubt experienced that feeling of exasperation that you’ve worked your tail off all week but aren’t fundamentally any further forward than you were at the start of the week — there’s been a lot of motion, but little progress.

Failing one success at a time is a strategy execution problem that many driven, accomplished people fall into.

It’s not that they’re not productive, action-oriented, and engaged people, but rather that they are productive, action-oriented, and engaged — they’re either stuck in an urgency spiral or they’re fixing the plane while flying it without knowing where that plane is going.

7 Questions to Reflect On

If you know you’re failing one success at a time, here are some questions to reflect on:

  1. What would you do in the next ninety days if you knew that your needs would be covered for the next six months?
  2. What major project keeps getting put off because urgent and important projects keep beating it in the project cagematch?
  3. Who can you talk to who has experience, vision, or perspective about the deeper waters that are right outside the edge of your known world?
  4. What one thing, if completed, would make all follow-on activities that much easier? H/T The One Thing
  5. Which of your projects or activities create a lot of work and motion but don’t seem to create real progress?
  6. What mindsets, habits, or routines are no longer serving you or your team? Is it time to leave the canoe behind?
  7. Have you updated your vision (or your team’s vision) of what’s possible for you, based upon your new capabilities? You’re probably better and stronger now than when you set out.

Without knowing your situation, I can’t tell you which bait to use, but I can at least point out places for you to fish. Far better to succeed slowly one success at a time, than to fail one success at a time.


Charlie Gilkey is an author, business advisor, and podcaster who teaches people how to start finishing what matters most. Click here to get more tools that’ll help you be a productive, flourishing co-creator of a better tomorrow.


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