100 conversations on meaningful work: 5 things I learnt in the process

Photo by Roven Images on Unsplash

In January 2018 I set myself an ambitious goal: to have conversations with 100 different people about the work they do and how they find meaning in it.

After two years of freelance and remote work I felt adrift. I no longer knew what I wanted or what made me feel fulfilled at work. I had been thinking a lot about purposeful work and had got so tangled in my own thoughts and ideas that it was hard to make sense of anything. My ‘process’ of finding my direction had become uncomfortably cerebral and lonely. I decided to start a few conversations with others to see how other people think about the work they do.

On a trip to Japan I found a daruma doll, which the Japanese use for setting their intentions for the year ahead. You colour one eye when you set the intention and promise to give the daruma its second eye when you complete your goal. Never one to keep things simple, I set myself a serious of SMART (specific, measurable, achievable(!), relevant, time-specific) goals….

         Have a conversation with 100 different people about the work they do

         Record an insight from every conversation (250 words minimum)

         Run at least five discussion events about purposeful work

         Publish 20 articles (500 words minimum)

The actual completion of all these goals turned out to be a bigger task than I expected – especially when you factor in fear, perfectionism, writer’s block, more fear and several relocations (San Francisco, London, Berlin).

But I was curious about the subject of purpose, and being someone who is usually terrible at finishing anything for myself, I was determined to see the project through to completion.

Here’s what I learned in the process:

* Getting outside your own head is always a good idea

Some people are predisposed to thought over action. This includes me. Much of the time I am convinced I can think myself to a solution. In reality, I tie myself in thought-knots. Having conversations with others freed me from the confines of my own brain! In the process I found like-minds and divergent minds, and in every conversation I learned something new.

* Don’t wait for perfection, or even anything close

You’ll be waiting forever if you do! Start where you are. Run the event and finish the article even if it’s not as good as you hoped.

Ira Glass said it best:

‘Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions.’

– Ira Glass on creative work

* Every (wo)man is your guru

I sought out a few particular people to speak to about meaningful work - those who I thought were in the best position to teach me. But I found some of the wisest pieces of advice in the least expected places. There are great rewards to staying open to conversation, to new people and challenging ideas.

* Intuition is a muscle, and it’s worth developing

We’re always told to trust our intuition, but it’s not always that easy! Sometimes it’s hard to know what exactly your intuition is telling you. But it works like a muscle, the more you use it the stronger it gets.

* Ambitious goals are worth reaching for

Setting goals that were just a bit bigger than I thought I could easily achieve nearly backfired – I am completing the last tasks on New Year’s eve! But in the process I forced myself out of my comfort zone and found I could achieve more than I thought.