I’d been wanting change for a while, although I didn’t know what it was that needed changing. There were just more weeks where I got to the end of them feeling drained, and those weeks seemed to be becoming more common. I’d looked at roles in other organisations because that felt like the obvious thing to do if I wanted something to change, but nothing I saw was enticing enough to make me want to leave for it.
Then I had another one of those weeks. My husband and I spoke about it one afternoon and, by that evening, I was mentally working through Tim Ferriss’s fear-setting exercise. The next day I sat down and actually wrote it out, and by the time I’d done that, the decision felt surprisingly solid.
That still feels slightly strange when I think about it because I’m usually a planner when it comes to things like this. Not so much for organising outings, trips or even meals! I prefer structure and knowing what happens next, at least at a high level, and I’m generally much more comfortable when I have a rough idea of the process. If I’d given myself another month to think about resigning, I’m certain I wouldn’t have done it. I probably would’ve analysed it more, found more reasons to wait, and stayed because staying was familiar and comfortable, even though by then I knew something needed to change.
The fear-setting helped because a lot of the things I was worried about had been sitting together in my head as one big unknown. Once I wrote them down and looked at what could happen and what I could actually do if it did, they became much easier to deal with. My husband’s support mattered too. Whatever I decided, he would support me, but he also thought resigning was a good idea. After I left, he told me to take a few weeks and decompress.
That was good advice. I just wasn’t very good at following it.
For the first couple of weeks, I felt as though I needed to be busy all the time. If I wasn’t working, then I was cleaning, doing things around the house, tidying something in the garden or finding something else that needed doing. If I sat down and read for a while, I felt guilty. The strange thing is that I already knew being busy and being productive weren’t the same thing. I’d said it to other people often enough. I also knew that having space to think was important.
But knowing it and actually doing it are very different things.
The need to be doing something was so ingrained that I hadn’t really noticed it. Even when I suddenly had the time and space I’d said was important, my instinct was to fill it. It was only after I’d had some time to decompress and process what that space was actually for that I started using it intentionally. Instead of treating thinking, reading or simply not doing something as time I needed to justify, I started making space for it deliberately. That shift has taken much longer than I expected, and I’m still learning to do it.
Once the need to constantly do something started easing, I began doing some self-coaching. I wanted to understand myself better and work out where I was heading. I really thought that would take a day or two, maybe a week at most. Through this journey, I’ve found that proper self-reflection takes time. It’s a process, and it can be difficult because you really have to think and answer yourself honestly rather than trying to just arrive at an answer. After years of working, that was very different from sitting down with a notebook, answering a few questions and expecting clarity to appear.
One of the things I started thinking about was how many of the roles I’d taken on over the years had come about because someone else had said, “Kirstin can do that,” “Kirstin would be good at that,” or “Kirstin could move into that role.” That isn’t to say I didn’t have a choice. I did, and I learnt a huge amount from those roles. But I didn’t stop often enough at different points and deliberately ask myself: where am I actually heading, and is that where I want to go?
Looking back, I suspect some of that thinking had already started before I resigned, even if I couldn’t articulate it properly at the time. I’d had opportunities to work beyond the boundaries of my formal role, including across different teams and on a global initiative, and I really enjoyed that kind of work. I liked being able to contribute where my knowledge or experience was useful, help solve problems and move across different areas.
The organisation I worked for was also unusually good at not pigeon-holing people into narrow roles. Even the formal roles were often broader than the traditional equivalents elsewhere, and the boundary didn’t stop at the job description. A tester, for example, wasn’t expected to hand over their test results and consider their part done. If the team was falling short somewhere, people collaborated, stepped in and helped. I valued that enormously because it gave me opportunities to learn, contribute in different ways and work across areas that interested me.
The downside was that it also made it very easy for me to keep taking on more.
I was stretching myself too thin without really understanding why I was increasingly feeling that my actual role wasn’t quite what I wanted anymore. When I started trying to work out what I wanted next, I found it much easier to answer a different question first: what don’t I want? That was surprisingly useful. I realised I didn’t want to lead permanent teams or spend most of my time dealing with day-to-day operational issues. I wanted more freedom to move between problems, contribute where I could add value and then move onto something else.
Knowing what I didn’t want didn’t suddenly give me the answer, but it was still an answer of sorts.
My view of career growth changed many years ago after reading Sheryl Sandberg’s Lean In. She describes careers as more like a jungle gym than a ladder, where you can move up, down, sideways or diagonally. That idea had always made sense to me. There didn’t need to be one straight route upwards, but throughout my career there had always been another place I could move towards.
This time, there wasn’t.
After resigning, I started exploring some of the ideas that had only been loose thoughts before. Board work was one of them. Business acquisitions was another, along with a few other possibilities. At first, I think part of me was still waiting for one of them to become the answer. I was used to there being another role, another organisation, another problem to solve or another part of the jungle gym to move towards. Surely if I explored enough things, one of them would eventually reveal itself as the obvious next move.
The self-coaching gradually pushed me towards a much bigger question though. Instead of asking myself what job or career I wanted, I started asking what kind of life I actually wanted. For me, a lot of that came down to quality of life and flexibility. I wanted to be able to decide when I worked. If I wanted to work at night, I could. If I needed time during the day for something else, I could take it. If there was a day when I didn’t want to work at all, I wanted to be able to make that choice too.
That was probably the point where I started realising I wasn’t necessarily looking for another conventional job or career. I’m not opposed to having a job. If I found a role that genuinely allowed me to work in that way, I would consider it. I just haven’t seen many job descriptions that say: work when you want, step away when you want, explore a few completely different things at the same time and decide for yourself where your attention goes.
The financial side still mattered too. I hadn’t suddenly decided that income or maintaining my independence wasn’t important. It was. The challenge became working out how to create both: financial independence and a way of working that gave me more control over my life. That is something I’m still working out.
And, if I’m being truthful, it can still be awkward when someone asks me what I’m doing now. I can say I’m building a portfolio career, but then the obvious question is: what does that actually mean? At the moment it means I’m exploring several different things. Some may become meaningful parts of how I work in future. Some probably won’t. If something reaches a point where I don’t think it’s going anywhere, I can stop and move onto something else.
There are moments when saying all of that out loud sounds unfocused, even to me. When there are several things on the go at the same time, I sometimes wonder whether it sounds as though I’m all over the place rather than deliberately exploring different paths. For most of my career I could answer the question very easily. I could give someone my job title and they immediately had a reasonable idea of what I did. Now the answer takes longer.
But I’m beginning to think that the difficulty of explaining it doesn’t necessarily mean there’s something wrong with it.
When I resigned, I thought having time away from my old role would eventually help me work out what I wanted to do next.
Instead, having the space to think changed the question.