#80: Uncertainty training

#80: Uncertainty training

This week I discuss how years of confronting OCD have prepared me to handle change and uncertainty.

These weekly updates share life with OCD as part of my Mental Work Health project to reduce stigma around mental health, especially at work.


This past week brought some major changes, which were not completely unexpected, but still surprising. Since the beginning of the year, I have been working for a new educational startup, Factor. We are clear and convicted about the problem we want to solve—helping teenagers prepare for life after school. Exactly how we were going to do that has been something of a question.

The problem is that we had assembled a team of eight amazing people to help figure out how we were going to tackle this. My friend, and our founder, last week realized that we had skipped some major steps and needed to make some adjustments. He needed to figure out more about how we were going to approach solving this problem, and make sure that we understood the problem completely before starting to build something.

In a reflection of his kindness and leadership, he came to us and shared with the whole team what he was grappling with. He hadn’t yet made a decision about how to approach things, but wanted to let us know what he was thinking and meet with each of us to get our thoughts.

As someone who struggles pathologically with uncertainty, this was difficult.

And at the same time, I felt calm and peaceful. I have complete confidence that we will be taken care of in the short term, and I trust that in the long term, I will figure things out.

I feel so fortunate and blessed that my skills and experience are in high demand right now, so if it comes down to it, I could probably find a new job easily. I told my wife that if I had to guess how things will go, I will probably contract with Factor for a few months until we have a better sense of what we need to build, and then there would be opportunity for me to go back full-time. But I don’t know exactly what will happen.

At this point, I am going to start moving forward assuming that I need to find some additional contract work to provide for my family. I don’t want to jump into a full-time position somewhere, because my heart is still with Factor. If there is the possibility to work on solving this problem full-time, that is my top choice, and I want to keep that option open for a future decision.

But seven kids and a mental health condition are not cheap. So I’ve got to find some projects to take on.

When I was telling my therapist about the situation, she remarked on how well I seemed to be handling this. I paused and reflected that all my uncertainty training was paying off. Yes, this is scary. But it’s also something I know how to handle. Most of my work in managing OCD is confronting uncertainty and learning to sit with it.

So now that I am faced with a major situation of uncertainty, my brain knows how to handle that. My body trusts me more. I have skills and strategies to approach the uncomfortable sensations.

In discussing with my therapist, I discovered another surprising truth—I’m excited. For years, I have wanted to be independent and self-employed, but the risk seemed much too high for our family. Well, now we are almost forced into the situation. I could certainly just go get a regular job somewhere. But since this is likely to be a short-term period before full-time work at Factor is needed or possible, it’s an ideal time to try this out.

One of the challenges I have been grappling with is how to approach this kind of work. Part of the issue for me is that my interests, and even experience, are so varied. I have worked as an iOS developer for years at this point, and that is probably where I have the most marketable project-based skills. But I also love sketchnoting. And design. And product management. And web development. And writing. And presenting. And public speaking.

So where do I focus?

I’ve been pondering whether it is better to try and define myself more narrowly to make it easier to seek and find specific types of projects. Or whether to just connect with people and broadly discover what kind of work they might know about that I could do.

The funny thing to realize is that it’s fundamentally the same question that I just boasted to be good at handling—uncertainty. My brain naturally jumps to a desire to create order in chaos. To organize the clutter. To find certainty.

Instead, I need to lean in to the uncertainty. I have never done contracting work full-time. I have done occasional projects over the years, but this will be a new experience. Instead of trying to wrap my mind around everything and get control, I need to be curious.

As I used to have to say over and over during my OCD treatment:

I can’t know for sure.


This will be an interesting time to try and put my training and skills into practice in a very practical way. It’s all well and good to write about how I can deal with uncertainty better, but now I need to live it.

One thing that I want to push myself to do is to avoid becoming rigid in my thinking. I can’t settle into a routine that becomes a compulsion. I can find activities and habits that help, but I can’t cling to them.

I need to approach my days with mindful curiosity. What do I feel right now? How can I sit with that?


The challenge that I issue myself, and invite you to accept as well, is to surrender. Stop trying to impose certainty on an inherently uncertain world. Accept that most things will remain unknown and unknowable. Move forward where possible, and be patient with the rest.

Remember to exercise a healthy amount of compassion. Change is hard. Especially for a brain that is pathologically rigid. Instead of getting discouraged, or beating myself up that I am falling back into old ways of seeking certainty, recognize it and adjust.

Be kind. It goes a long way.

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