Making big personal decisions

They are just not.. objective”, said Lumi.

She was right. Indeed, friends and family are not always helpful when you need objective feedback.

I had met Lumi a few weeks ago at an event where I mentored her on how to become a tech conference speaker. She wanted to give a talk to share with others her technical experience and knowledge acquired at Zendesk where she worked. While I expected our catchup to be on her progress with her becoming a speaker, the conversation changed direction and became personal.

At the Dublin Global Diversity CFP Day at Zendesk. Lumi and I are in the front row. I’m in the middle and she’s on the right.

Never go to your mom

“I don’t go to my mom for advice as much”. Her words reminded me of the book on customer validation for startups called The Mom Test. It explains that if you go to your mom and tell her you have this idea about whatever, digital broccoli, she’d say “omg, fantastic ideat!” Yes, your mom is lying to you. She wants to be encouraging and doesn’t want to hurt your feelings. The book advises how to avoid such conversations when you are validating your startup idea, as people don’t want to hurt your feelings.

Something similar happens when you go to your parents for a big decision. That’s even more likely when the decision requires courage. For example, if you are to change your career and start from scratch or if you are to separate with your spouse. The unknown that scares you happens to scare them even more.

Again, your mom would like to protect your feelings getting hurt. She could try to keep you in the known, the safe, and thus discourage you from making the change.

“Who broke up with who?” It was important for my mom to know who initiated the separation between my long-term ex and I about a year ago. She seemed upset, disappointed, and irritated. I can only guess what caused that reaction. Yes, it meant that grandchildren were getting postponed. It also meant that I’d probably be exploring new relationships and that means not being as safe as in an eight-year relationship.

Sometimes don’t ask your friends

Whenever I have shared about changing a job, moving country, moving in with a partner, my friends have always been encouraging.

It was different when I shared that my ex and I were separating. I was excited, while the reactions I got were —

“Oh, come back to me in three weeks. This is temporary.”

“I think you are trying to convince yourself that you are happy. I mean you were to get married in a few months..”

“I am.. so sorry to hear that.”

That was the majority of the reactions.

I also did get a few “I’m so happy for you, I could see that you were not being fully yourself in that relationship.”

When my ex and I decided to separate we didn’t discuss it with anyone. Or at least I didn’t. And I’m glad we did it this way, because only we had the context.

On a Friday morning we were chatting in the bedroom. I had made a list of the things that didn’t work in this relationship and read them out loud. She agreed. They were the type of things that you can’t work out. Putting them down helped me a lot to be objective about it. I still have the list in my phone notes somewhere. Having that written down gave me clarity and I never questioned if we made the right decision.

Lumi’s brilliant approach

I shared some of that story with Lumi. She was entertained by it. “I went through something similar a year ago.”

While the story made me feel really close to her, as there were a number of similarities, something else stood out.

“I don’t really ask friends or my mom for advice as much anymore.” Then, she revealed with me her approach. She writes down a question to herself. Then she answers it. Then, she asks herself another one. By writing it down, she creates a distance that allows her to be objective. And she keeps doing that by the moment she gets to the answer and makes the decision. The key thing is that she manages to ask herself the right questions.

My eyes went wide open. That’s like doing a Q&A with yourself. Brilliant!

Being objective

It’s not only objectivity that we need when we go to ask someone for advice. We need acceptance, guidance, and encouragement. If you don’t want to trade one for the other, I could help — vessytash.com

I can create an environment where you feel comfortable sharing, help you structure your thoughts, and ask you the right questions.


Curious how you can reconnect with yourself, especially at times of making big personal decisions?

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