How to Fail and Still Win Big

Like anyone else before starting a commission-only job in sales, I questioned whether it was the right decision to try it. I’d had a few months experience of a lead generation job, but I’d never made a sale in anything in my whole working career to date.

So I played through a few outcomes in my head. What if I didn’t do very well? What if I made no sales? What if I came out with less earnings than if I just stayed in my current job working at the front desk of a hotel?

I came to the conclusion that it was reasonable that I would find the job very difficult, and there was a chance that some of those outcomes could indeed come true.

But even if I did “fail”, and earn less than what I would have had I stayed in my job at the time, in what areas would I still win? I would probably at least make a few friends, I would have travelled to new parts of the country, I would have learned at least a few transferable skills, and I would surely have practiced overcoming objection. Even if I made the slightly less money than before but still achieved the other things, I would still have counted that as a big win. At the very worst, I would potentially learn to never do a sales job again.

In the end, I did find it even harder than I thought it would be. There were whole workweeks where I didn’t get paid a single cent for my time and effort. At one point in the year, I went 20 working days without making a single sale – not a single commission. But overall, I had some better periods and I ended up making about 1.5x what I would have if I stayed in my hotel job.

What’s even better, as is the nature of commission-sales, I ended up getting better and better over time, meaning in my second year doing the job I ended up earning just over double of what I would have in the hotel. In my third year, I ended up earning about 5x what I would have in the hotel – I doubt the hotel would have given me a 4% increase in my pay within that time, let alone 400%!

The idea of putting yourself out there to potentially “fail” in order to still win big is sort of related to Robert Kiyosaki’s rule of “working to learn, not to earn”, but also can be applied outside of decisions at work too. Failing to hit a 45 minute goal for a 10 km run still means that you completed the race faster than the average runner, and you still get to reap the rewards of the fitness built up through weeks or months of training. Failing in a relationship, but coming out of it learning more about who you are or what kind of partner would suit you the best is still winning big in the long-term.

Which life situations have you flirted with failure and still won big?

Back to Square One or Back to Base Camp?

Failure is inevitable throughout life. But when failure occurs, we can sometimes think of giving up on our goals or go straight back to square one. But we don’t have to go all the way back to the start.

Instead, we can imagine it more as if we were climbing Mt. Everest and weren’t quite able to summit. Instead of going all the way down the villages at the foothills of the mountain, we can simply regroup at base camp. That way, we can stay acclimatized to the high altitude, and try again to reach the peak quickly instead of going all the way down the mountain, losing momentum and wasting energy.

When we pursue goals in life, we usually learn so many things on the journey that build on our skills, mindset and experience. Just like in mountaineering, we become acclimatized and fitter both physically and mentally. If we then fail, it doesn’t mean that all the development and progress has been completely lost – as long as we pick ourselves back up. If it’s really a worthwhile goal, have the resilience, grit, and determination not to go back to square one.