When Feeling Like You’re Failing Isn’t Failure At All…

A client recently told me “I constantly feel like I’m failing.” It stopped me in my tracks because every business owner knows this mindset intimately.

As small business owners, that feeling of failure often hits hardest when we’re not seeing immediate results – even when we’re doing everything “right”. We have solid foundations, we’re learning from setbacks, we’re taking calculated risks. Yet the failure mindset persists.

But here’s what I’ve learned about transforming this mindset: Sometimes what feels like failure is actually staying true to your values and business model.

I faced this myself when I had to step away from a major project that promised significant future opportunities. I was so invested in this one client that I’d let other parts of my business slide. The project was consuming my time and resources, and their approach to business increasingly conflicted with my values. I’d drifted far from my core business model in pursuit of potential gains.

Letting go felt like failure. But it wasn’t. It was a necessary reset.

Real transformation in business comes from two things:

  • Knowing when to hold your nerve because your strategic foundations are solid
  • Recognising when you need to let go of something that isn’t sustainable

The key is knowing the difference. This requires both self-awareness and self-regulation – skills that often need more attention than our business plans.

When that feeling of failure creeps in, I now stop and apply the same strategic reset methodology I use with clients:

  1. Identify the real problem
  2. Get to its root cause
  3. Find existing solutions and opportunities
  4. Plot these on an effort/impact scale
  5. Create and implement an action plan

Sometimes what feels like failure is actually just the discomfort of staying true to your path. The real failure would be compromising your values or business model for short-term gains.

Remember: Change takes time. Trust in incremental improvements over quick fixes. They might not show immediate results, but they build something that lasts.

Transform Your Business Mindset

Download my “Sailing Forward” exercise – a practical tool designed specifically for business owners to transform feelings of failure into strategic direction. This visualisation technique helps you identify what’s moving you forward, what’s holding you back, and how to chart a clear course to business success.

[Sign up below to get your free copy of the Sailing Forward exercise]

The sailing metaphor isn’t random. As a country kid, I spent holidays learning to sail on my uncle’s yacht ‘Defiance’ on the Swan River. Every business lesson I teach today started there – but that’s a story for another post.


Follow me on LinkedIn this week for my series “Lessons from a Boat Named Defiance” where I’ll share more insights about navigating business challenges.

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