Entrepreneurship | Life Lessons

On Failure, Entrepreneurship, and Next Steps

Os Ishmael
7 min readJul 9, 2024

Reflecting on business setbacks and the lessons they teach you.

Image by author via DALL-E

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There is nothing quite like a setback in business to transport me instantly into being an entrepreneur experiencing the first flush of disappointment.

The sense of failure that you will feel like this forever, that you won’t be able to stop thinking about it, that competitors will move on quicker than you will, that you will see them succeed and your heart will sink.

But as bad as it feels, somewhere in there is a sense of pride that I tried, that I yet again put myself out there even though it’s hard, as well as an immovable knowledge that however much my heart aches, that I will be okay, and will thrive and be well. This is not how I felt when I was starting out, and certainly not in my twenties.

Are we any wiser?

Age gives us wisdom, however, it’s still not easy. If I want to reflect or strategize, I have to look no further than my failures, which hold the lessons, and the timeline of my efforts to now.

But then again, when people want to reflect, they’ll find a way regardless. When I was younger, if I wanted to…

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Os Ishmael

Fractional Chief Communications Officer embracing life's wisdom | By day crafting strategic communications and narratives | At night, asleep.