Worries & Independent Life
And 5 ways I cope.
Nit-picking has been an occupational hazard for me since forever.
I recall someone from my team coming to me once. The number of tracked edits I had inflicted on her paper was causing her some distress. My answer was not to worry. I was doing the same to everyone else in the team. I assured her that her appraisal would be fine.
I’ve a slight streak of OCD in me. And I suspect it’s time for some karma. Worrying about small things when working a full-time job, especially in MAS, is generally a positive thing. Especially when you are drafting acts, regulations, or clearing contracts involving significant stakes.
And this week was a crazy bad one for this OCD. A talk for the leadership of a Ministry. A briefing to the board of an insurer. A talk for civil service directors doing a leadership programme. Three training sessions. One for a digital asset company. Two for senior leaders of a bank coming to Singapore for an executive leadership programme. Contracts after contracts. The launch of the JobAQ platform I did with Stephen Tracy. I was so tired at the end of a week I crashed and napped and missed a night call with someone from Toronto discussing training for some international regulators.
As an independent, I find the habit of worrying too much to be a bad thing. The stakes are way smaller. But I still worry before every talk. I read every contract twice, pass it through AI, then read again. And then worry about what the other party will think about my pushback. I check the demo the night before and again the morning of. I worry about the increasing number of ‘nos’ I say. These days I even have a niggling worry that something I wrote will be seen as AI generated.
But I think I am starting to learn how to deal with it. Sharing how it looks from the inside of independent life below. And my five rules for dealing with it.
The worry before and after every room
The engagements that stressed me out for the week.
Before the session for the leadership of a Ministry, I kept wondering why my deck, which came from my boring perspectives in the financial sector on AI governance would be relevant. I was quite happy that I connected them to Dr. David R. Hardoon who had a broader and more exciting perspective than me and that he would go first. Though I had secretly wished that they would feel there was no need for me.
Before the briefing to board of the insurer, I was worried about the relevance of my slides to their world. I’m not and have never been a director of a board. While I had staffed the MAS board for two years, that was mostly administrative. The session went smoothly. And there was one win. Someone said that a pre-read I wrote and shared was certainly not boring. But my internal spidey sense told me I had not given them exactly what they needed.
The two sessions for the senior leaders of a bank coming to Singapore for an executive leadership programme was worrying in a different way. The material was familiar to me. But it was a crowd that needed the material to be in Mandarin. There were translators, but conducting training through an intermediary is usually challenging. I tried using my half past six Mandarin (my entertainment diet is usually Mandarin shows on TVB, iQiyi and Viu after all). Was that a win or lose? I was not sure.
Even someone asking for my bank account for the honorarium of a paper on evaluation and testing for Agentic AI I wrote worried me a little. Because that meant the paper was done, and I worried if I had checked it enough.
By the end of the week I was in a heck-it mood. And I told the room of civil service directors doing a leadership programme that my aim for the 30 min talk was to make AI boring to them. And that my secret wish was that AI would become boring and fade into the background so I would not need to do any more of these panels and talks.
And I filtered contracts that could have led to some risks. One only paid for delivery but buried deep in its agreement was one line that would have transferred the rights to my IP to them. And there were other more minor things that needed to be caught.
This is what independent life feels like from the inside. Most probably think it’s freedom. From emails from bosses. From KPIs. From worry.
That’s not the case. All the worries remain. But all of it is yours alone to bear. No team to catch the error. No colleague to sanity check the piece. No institution to absorb the mistake.
So you check. Then you check again. And check one more time.
What I think one can do about it
First. See the stakes for what they are. Most of the time they are not as high as the worry makes them feel. The habit of treating everything as high stakes is a residue of environments where things actually were. Most things aren’t. Be clear about the real stakes. Don’t imagine them.
Second. Diversify. As much as possible. When one thing carries all the weight, the worry amplifies. Spread the load across enough engagements, projects and relationships and no single one becomes existential. It’s not just money that allows one to walk away. Choices help too. This is also just risk management 101.
Third. Detach from the outcome. Deliver the best you can. Then let go. The worry almost never predicted the outcome accurately anyway. The rooms that stressed me most often went fine. The ones I felt relaxed about sometimes went flat. That latent worry is a bad forecaster. Stop consulting it for predictions.
Fourth. Know your redlines. Not everything in a contract or a conversation needs to be negotiated. But some things do. Being clear early about what you will and won’t accept turns anxious reviewing into decisive filtering. For engagements themselves, use money and relationships as the filter. Calibrate your redlines of what you will do and not do based on how much you like the person vis-a-vis the remuneration. The more you like the person, the less money matters. And vice-versa. The worry shrinks when you know exactly what you’re protecting and why.
Fifth. Lose yourself in something that has nothing to do with any of this. For me it’s a watercolor every night before bed. One hour where presence is required and the worry has to wait. You cannot paint and worry at the same time.
#IndependentLife #Worries #AIRiskManagement #Transitions #Reflections
Try it.
#IndependentLife #Worries #AIRiskManagement #Transitions #Reflections