3 - Deciding When To Start A New Startup
My last post covered how I decided whether to start a new startup. The next question was when to start. Answering these two questions overlapped, with the final decision of when to start only being possible after deciding whether to start.
Here’s how I approached the when to start question.
Creating Space
I left Chaser in July 2020. My daughter Alice was born five months later. Jess and I agreed early on that there was only room in the house for one new baby at a time, so a new startup would need to wait until the second half of 2021 at the earliest.
Alongside this family imperative was a personal imperative to create space. One of the most impactful books I’ve read in the last year is Transitions by William Bridges, which carries the informative straplines of: making sense of life’s changes; and, strategies for coping with the difficult, painful and confusing times in your life. He distinguishes between change and transition. Change being situational; transition being psychological. With transition being about inner reorientation to incorporate changes into your life. Without it, change is just a rearrangement of furniture. In seeking to replace missing elements as quickly as possible, we treat ourselves like appliances that can be unplugged and plugged in again. In doing so, we forget the importance of fallow time, winter and rests in music. We miss out on the fallow and fertile time between endings and new beginnings, which he calls the neutral zone.
This resonated with me. I’d been doing Chaser for seven years. As a rule of thumb, I apply the following equation:
It was then about creating that space. When I left Chaser, I speculatively mentioned in my post on LinkedIn about being available for consulting work. Responses from there and generous recommendations from my network gave me the bridge I needed. A lesson for me was how easy it can be to take your own knowledge for granted. We all have skills and expertise that can valuably benefit others if we use our resourcefulness and initiative to find the opportunities.
Time in the Neutral Zone
The first step of making the most of time in the neutral zone was letting go of the old. Outwardly, this was pretty straightforward. Inwardly, it was more complicated. It was about changing a definition of who I was that had grown seven years of roots. My advice to anyone in a similar situation would be to be patient - there is only so much you can do to truncate this process. Getting frustrated with yourself is only going to be counter-productive. And secondly, to help yourself by going cold turkey as much as possible. Stop following on social media. Observe your thoughts and challenge yourself. For example counting and then trying to reduce the number of times you think about the no longer relevant old, or lengthening the gap between thinking about.
Then in terms of seizing the opportunity of time in the neutral zone, the following activities helped me:
Working with a coach as a thought partner
Writing and journaling to organise my thoughts
Reading - I’ve been really fortunate to tap a rich vein of works in philosophy, psychology and success literature. I won’t post the list here. When I see reading lists like that it intimidates me with an “oh no, more books I haven’t read” reaction. And my Amazon wishlist promptly gets even longer with books I’ll never get a chance to read. But if anyone is interested please either reply to this post or email me on davidtuck1983@gmail.com. I’ll be really happy to share.
All of these activities underpin and support the process of reflection. Seven years is a huge body of raw material. Steve Jobs talked about how you can only join the dots going back. I think that’s especially true as an entrepreneur. There is a huge opportunity for perspective at the end if actively seized. The neutral zone is the opportunity to turn that raw material into insight and growth.
New Beginning
There is a lovely line in Transitions that I have found to be true:
“When you’re swimming underwater, the longer you can hold your breath, the more interesting a place you’ll eventually pop up”
I’m so grateful and excited for where I’ve popped up. But if there is a science to when it’s time to do so, I don’t know what it is. It’s a qualitative “when you know, you know” situation. Some observations from my own experience that can serve as indicators of when it’s time for the new beginning:
When I described myself to Jess as feeling refreshed, refactored and ready. Refreshed is a point I haven’t covered. But suffice to say, running a startup is draining. It’s key that the battery is fully charged. Refactored is a software engineering term for improving the internal structure of the code to make it run more efficiently. And ready is, well, ready!
I’ll endeavour to avoid quoting the same person multiple times in future posts. Jobs said about his first departure from Apple: “The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life”. I really identify with that lightness and creativity; seeing tantalising new opportunities in familiar places. You know it when you feel it.
At the end of March 2021 as I started to see the end of the neutral zone on the horizon, I set myself the goal of deciding on a problem space for my next startup by the end of the second quarter (June). And to have wound down all consulting work by the end of the third quarter (September). I’m glad I gave myself those forcing factors. For whilst the neutral zone was a rich and invaluable experience, there is a risk of procrastinating and drawing out the time there.
The process of deciding what that startup would be will be the subject of my next post. Thanks for reading and stay tuned!