Getting to know my should-self.

What I’ve learned from doing a job I’m really bad at for the last 6 months.

For the past six months I have been working in an extraordinary and fast-growing tech company, doing a job for which I am totally unsuited.

Six months earlier, at the end of 2016, I was just a few weeks into a role at independent creative agency, For The People. I was doing great work with smart people. I had found my feet and a sense of belonging. I was happy.

Despite all this I’d been interviewing on the side at an up-and-coming, IPO-tipping, $2.5bn-valued, sparkly unicorn. And to my surprise I was offered a sales role in one of the company’s most successful teams.

I said goodbye to For The People and flew back to the UK for Christmas with my family. I was back on a flight, this time from London to Salt Lake City on January 1 2017 to start training. Even then, sitting on the plane, I knew in my core that I’d made a bad decision. Over the next few weeks and months, I verified that instinct.

Trained up and back in Sydney. I found myself doing a job for which I was simultaneously under-qualified and over-experienced, and had little real interest in doing. I put my head-down, charging towards my metrics, and trying to learn much as I could about the sales process from skilled and supportive colleagues. But I knew it wasn’t sustainable. I finished up after just under six months in the job, at the end of last week.*

So what had led me to make such a bad decision?

Long before this point, I had decided that I needed to get into a top-tier tech company before I turned thirty.

Taking into account previous experience, I’d narrowed my focus on B2B SaaS companies. But beyond this, I had done very little reflection on what type of work I wanted to do or why I’d set this goal in the first place. It was a thin ambition but it had built up in sticky layers over time:

Several of my friends and previous colleagues were, and still are, working at the like of Google, Facebook, LinkedIn, and Airbnb. Over the last few years, I’d listened in awe and envy to their tech tales of training trips to the US, product launches, bumping into Sheryl in the corridor. My bookshelves read like a who’s who of women in tech. My Twitter and podcast feeds were jammed with Silicon Valley and start-up handles.

In near unconsciousness, I had written a career plan and vision — not on what I enjoyed or was good at — but on the basis of what I thought I should be doing.

– “That’ll be your should-self” my wise friend said as I sobbed pathetically down the phone mid career crisis. 
– “My should-self..?” 
– “Yeah, you let your should-self take over.”

We all have a should-self

S/he is the best version of you as told by your inner-critic. S/he’s based on a thousand little observations, influences, comparisons, and measurements.

S/he can influence all aspects of your life; work, relationships, parenting, how you spend your free time and where you spend money. In every scenario, there’s a gap between where you are now and where you think you should be.

Of course, your should-self probably does great work. Setting the alarm for 6am yoga; keeping you connected to old friends; putting his/her hand up for new projects and challenges. But left unchecked can lead you into the position I found myself in — disconnected, miserable, and utterly confused about the fact I hadn’t found my professional utopia.

When I reflect on my decision-making process six months ago, it’s obvious now that I was listening in blind faith to my should-self rather than, well, myself. To the point where everything I told myself and others supported what I thought I wanted. So much so that even my closest friends were thrilled for me when I walked into a job that was a terrible fit for my skills and personality.

For a time, I was pretty embarrassed about the predicament I’d got myself into; I even considered sticking it out for a year or 18 months so that I didn’t have to admit my mistake to coworkers, friends or family.

I got over this with a big gulp of pride and a several conversations with some very generous old colleagues and mentors.

The last six months have been the worst of my career, but they’ve also been the best. I’ve learned about what type of work I’m good at and what enjoy. I’ve also closed off some options and come to terms with a few things I’m definitely not going to do with my life and career.

Of course, I also got to know my should-self.

She’s still there now, making recommendations in the background. Some of them great, some of them a little questionable. At least now I know when to pay attention.


*I wrote this in June 2017, the week after I left aforementioned unnamed tech company. A week later I rejoined For The People and for the last three months, almost to the day, I’ve been doing great work with smart people, happier than I’ve ever been at any point in my career.