Why we need to fail more deeply, not widely

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“So how has your year been?”

Time appeared to freeze as soon as those words left her lips. It wasn’t a difficult question to answer, but at that moment my mind went into a time-warp as images of key events in the past 12 months flashed across my mind. I think I might have relived the past year in about three seconds.

Cool cool cool.

If I’m being honest with myself, this is probably the first time in my life that I can confidently say that I’ve had a good year. No scratch that, I’ve had a great year, both personally and professionally.

This year, I’ve tried and experienced many things; I started to develop my own personal brand, took up a writing course, added 20 more books to my reading repertoire, started and sustained a weekly exercise routine, consulted for a local start-up, started my life coach training, took up leadership courses, and started to build my own private coaching practice on the side, just to name a few.

However, there’s a whole lot more that I’ve done but actually failed at. In fact, some of the successes above also had a flip side to them, and this was perhaps the most important lesson that I’ve learnt from all of these experiences: these wins were a result of not just failing more often, but also doing so deeply.

Signpost at a water park with too many directions
Photo credits: twenty20photos

We’ve got 99 problems, but we can’t solve all of them

The way I see it, winning in life is pretty much a numbers game; the more things we try (input), the more results we will get (output). It’s simple arithmetic.

Now, I’m not suggesting that we pounce on every single chance we get to try something, new or old. No, we have got to be smart about it.

Transitioning from my 20s into my 30s taught me two lessons (so far).

Firstly, we only have limited time, energy, and physical and mental capacity to actually work on things in our lives. Jay-Z wasn’t kidding when he said we’ve got 99 problems to deal with. Maybe more, maybe less, but you get the idea.

And this brings me to my second lesson: we need to choose our battles wisely. We have to focus our limited resources on personal projects like how a magnifying glass focuses the Sun’s rays into a single spot. Scattered efforts make little progress, so it will be better for us to focus instead if we want to make meaningful progress.

Personally, while other people make impulse buys on clothes, electronics, or whatever catches their fancy, I make impulse buys on online courses that teach subjects that I might be interested in – investing, digital business management, online marketing, and leadership, just to name a few.

So earlier in the year, I signed up for four online courses. However, I still had a couple of courses “leftover” from the previous years. Long story short, while I spent a considerable amount of time going through parts of the courses, I didn’t complete them, and hence wasn’t able to fully apply them into my life since the learning was incomplete.

It wasn’t until I decided that this has to stop and I should see a course through to its completion did I start to see changes in my life. When I doubled down on a particular topic, I could appreciate it in its entirety, and that led to results.

Black dog sitting at the start of a fork in the road in the middle of a huge plain
Photo credits: Mint_Images

Don’t change course when we fail the first time

“Failure is the opportunity to begin again, only more intelligently.”

Another takeaway from my experiences in the past year was that I was too “flaky”; the problem many of us run into when we’re trying to achieve something is that when we fail, we turn around and move on to the next thing.

Here’s why this does not serve us at all: When we’re too eager to switch courses when the going gets tough, we deprive ourselves of the opportunity to reflect on what truly went wrong and what steps we can take to achieve better outcomes when we try again.

Now, if we choose to stay the course, we get to test our assumptions and hypotheses again and see what works. It’s like how Thomas Edison made 1,000 unsuccessful attempts at inventing the light bulb. If he hadn’t persisted, we’ll probably still be living in the Dark Ages today, literally.

You might not know this, but I’ve changed the tagline on the homepage of this website at least 20 times now. And that is totally fine because I’m still in the process of discovering who my ideal coaching clients are so that I can best serve them to the best of my ability.

Eventually, things will work out. And not only that, our wisdom is now so much more robust because we also now know what doesn’t. Treat each failure on the way to achieving the goal as a necessary stepping stone in the journey. Stay focused. Stay the course.

Young girl dribbling a basketball in front of a sunset with style
Photo credits: Mint_Images

Failing forward, hard and fast, to greater success

Going into the new year, I’m making a promise to myself that when I do fail, I will do so more deeply instead of widely. Hopefully, this would translate to more wins along the way.

It wouldn’t hurt to think a little more about the things that we’ll be investing our time and efforts into. Consider what does it mean to us objectively, but don’t discount how we feel about it as well.

Best-selling author Seth Godin once said, “One of the rules of this game is, the person who fails most wins.” I’m nowhere as wise as this amazing person, but for me, I’d think that the person who fails most deeply wins, not widely.

Here’s to more lessons and more wins in the new year. Cheers!

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About the author
Terry Toh

Terry Toh

Terry is an aspiring life coach working towards his accreditation by the International Coaching Federation. He loves to read about personal development and entrepreneurship, often with a nice cup of coffee or G&T in hand.
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