Failing Forward

I’ve never been a New Year’s Eve guy when it comes to marking the passing of time, for me it’s all about seeing the leaves back on the trees.

There’s something about spring when it finally hits, it gets me thinking, reflecting over the year gone by and gearing up for the challenges to come.

Each year, I make it a habit around this time to sit down and make two lists:

  • What did I succeed at in the last twelve months and why?
  • What did I fail at in the last twelve months and why?

It’s a useful exercise but beware, it takes a bit of intestinal fortitude to make it really valuable! You have to be prepared to answer both questions truly honestly. The point of the exercise isn’t to make yourself feel better, it’s to cooly evaluate what actually happened in your business and beyond.

And each year, before I start on my lists, I take the time to read back over entries from the last ten years or so. The interesting thing I’ve noticed is that it’s that second list – the failures – that I’ve consistently learnt the most from.

It’s a topic that came to mind while listening to a recent podcast episode of Empire Flippers where they interviewed Dave Schnieder, the owner of In it, he goes deep on some of the choppy waters he’s encountered on his entrepreneurial journey so far.

It’s a great listen and I really appreciated the honesty on display from Dave, along with the earthy good humor Justin Cooke brought to the subject as an interviewer.

I firmly believe a lot of younger entrepreneurs stand to benefit from listening to concrete examples of real-life business obstacles like the ones Dave and Justin go into here. In industry, and as culture, we over-fetishize success and sweep far too many of our failures under the rug instead of sharing them so others can learn.

I’ll be coming back to this subject over the next few months and picking out some classic tales of initial failure and challenges met that have inspired me so stay tuned.

If you have any favorites of your own, let me know in the comments below and I’ll look to include them. Fail forward!


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