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Not ready, but I’m doing it anyway

50 metres from the fork in the road I had to decide, “where do I want to go from here?”

To the left was a detour of about 7 kilometres; on the right, a more direct route that would have taken me home in about 3.

It was an exceptionally warm day; I hadn’t ran this far in ages; and I wasn’t feeling great.

My mind told me, “running literature recommends the direct route on the right. You haven’t built up sufficient mileage in recent weeks; you aren’t sufficiently hydrated; and the weather’s only going to get warmer.”

In short, I wasn’t ready for the detour on the left.

But I took it anyway.


When I applied for my first job, I was asked if I knew pivot tables. “Yes,” I said. “Great,” the recruiter replied. That night I spent an hour researching what pivot tables were and another hour practicing it. I aced the interview test on pivot tables and eventually got the job.

I wasn’t ready. Did it anyway. And then I was.


When I applied for my second job, the job description that was provided me said, “MBA preferred,” among a list of other nice-to-haves that I did not have. I didn’t feel ready. Not by a long shot. I applied anyway.

I passed the first round of interviews; and then the second. And then a third. At each round of interviews I learned more about the job. The more I learned about the job, the more I learned what was required. The more I learned what was required, the more I knew where to focus my attention on. With each round I’d become a stronger candidate. I got the job.

At the end of all the interviews, I had on hand a much clearer idea of what success would look like in this role. In the weeks leading up to my starting the role, and in the months following, I continued studying and researching how best to carry out my role. It’s been six years now, and sometimes I still don’t feel “ready”, but I think I’ve done decently well.

I wasn’t ready. Did it anyway. And then I was.


In one of my first major projects I was tasked with developing a forecasting tool for the Sales team. It would be used by the whole sales force, from frontline to senior management. There was a laundry list of requirements and it needed to be done by a date weeks earlier than I would have liked.

“Sure,” I said, a million doubts singing at the back of my mind. A few weeks and many overnight programming escapades later, I released the tool, and it’s been in use for almost five years now, and has been one of the most successful projects I’d ever done.

I wasn’t ready. Did it anyway. And then I was.


And similar stories emerge when I took on a management role; when I introduced machine learning to the sales team; and when I emceed at the company’s year-end event and the Sales Kick-off a few months later. Or even when I ran a marathon last December – when I signed up I definitely wasn’t “ready”.

In all the most important and exciting challenges that I’d put myself in, I’ve never been ready.


Still, it hasn’t been easy ignoring my mind who cowers instinctively from such challenges with a “but you’re not ready!”

  1. On the pivot table question I panicked after I said yes – I almost said no.
  2. On the application to my second job I was filled with self-doubt and constantly second-guessed myself – I almost gave up pursuing this opportunity.
  3. On the forecasting project I pushed back hard on timelines and only agreed after making very sure on the scope – I almost gave in to the temptation to say this was something IT should be doing.

I’m glad I took the detour on the left. Because now if I had to do it again, I’d be ready.

Categories: Career Psychology Running Self-help

Donn Lee

I love to read and write. Professionally, data science, technology, and sales ops are my thing. In my non-professional life, I aspire quite simply to be a good person, and encourage others to do the same. For those who care, I test as INFJ/INTJ (55/45?) in the MBTI.

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