Why I'm terrified—Making hard decisions

As I write this I’m on a flight to a destination I have no particular business being in—San Francisco.  I’ve felt like I should be there for quite some time now that I finally decided to give it a shot. 

Some of you may already know, but for those who don’t, I recently left the startup I was working at and moved out of NYC. 

Not for any negative reason, it’s actually the opposite. I served my purpose while there and am on to figuring out what’s next for me with the support of my former team. 

Fortunately, I’ve managed to leave all of my previous work engagements on good terms. I’ve realized leaving on good terms is a skill in of itself. 

Saying no to an opportunity is almost always harder than saying yes. The reason is if you say no, the other person may become ‘better off.’ 

Yeah, it’s counter-intuitive. What we’re afraid of is not the person becoming ‘worse-off’ without us but ‘better-off.’ 

To feel good about ourselves, we tell ourselves that we’re worried about the other person losing out more often than is the case. 

This illusion causes us to commit to things we don’t entirely care about or to stay in situations we don’t want to be in longer than we should. This applies to all forms of relationships, romantic, family, friends, etc…  

Ripping off the bandaid hurts. Saying no, hurts. 

This is why making hard decisions is, well, hard. 

What I’ve learned is that it doesn’t have to hurt as much or be as hard. 

Here’s the secret: 

Through awareness that you’re worried about the person becoming ‘better off,’ you can catch yourself. Instead, you focus on finding a way to make the person you’re saying no to better off. 

It may not always be possible to do this though. However, what matters is that you try anyways. The effort isn’t wasted because you’ll feel better having done it than not. 

Let’s use an example, you’re thinking of leaving your current job. 

Help find a replacement. If you can’t, create an instruction manual for the next person to do the job better. Your employer is now better off without you and you assisted in making them so. 

An example where it doesn’t work, you break up a long term relationship. 

Tell the other person what they were doing wrong. They may hate you for it but it’s better they know the truth than not. They may even appreciate you for it in the long run. You’ll also feel lighter for letting your emotions out.

Now back to the story, why am I going to SF and what am I going to do? 

The simple answer is—I’m figuring it out. 

For those who’re inclined to learn more: I don’t have a job offer and no one’s expecting me there. I am working on a side project that may turn into something more but that’s to be determined. 

I plan to travel for the foreseeable future as I figure out what I want to do. 

I’ll be back in Seattle from Sept. 21st onwards.  

Lighting a Match

A post I’ve deeply enjoyed learning from, maybe you will too.

“I used to be afraid a lot. Many of my childhood memories consist of days spent in a perpetual state of worry over one thing or another. I dreaded going to the dentist and going to get vaccinated. I wouldn’t talk to the girl I liked in my class because I was scared the other kids would find out I liked her and tease me. I’d come home from school alone and stalk around the empty house looking for intruders, scared and yelling in my most intimidating ten-year-old voice. As a teenager, I was scared I’d get laughed at in gym class because I didn’t look as manly as some of the older guys. Wherever there was a possibility of something unpleasant happening, I was there, worrying about it – often many days in advance.

I felt guilty. If there was a chance I might have hurt someone or misrepresented the facts even slightly in something I’d said, it would eat me alive. I wouldn’t cross the street anywhere but a crosswalk, even if all my friends did, because my parents had told me not to and I knew how badly I would feel about going against their wishes.

I never skipped class. Not even once until my junior year of high school. It was like the possibility didn’t even exist in my head. I didn’t smoke or drink in secret. I had to get the right grades, I had to get into the right school, I had to… because if I didn’t, then… then what? I didn’t even dare think about it, but surely something unfathomably horrible would happen and everything would be completely miserable forever.

After graduation, I went into business for myself. It consumed my whole life. I had to make money, because without lots and lots of money, I was sure I’d never have the kind of life I wanted. I wasn’t happy, and as far as I was concerned, I would never be happy until I was rich. I hated the work I forced myself to do, but the fear of what kind of life I would have to face if I didn’t make money spurred me on like a slave driver. I thought of it as “determination” at the time, but it was fear. I wasn’t so much running towards where I wanted to be as I was running away from where I was.

I wasn’t alone…

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  • In San Francisco from the 7th to the 21st

  • Going to be in Seattle from the 21st onwards

  • Recently hired an executive coach, have learnt a lot about myself in the process

  • Back to reading and writing a lot