How not to ask for help (Ricky Weekly #32)

This is where I share 3 things every week with my friends and anyone else interested.

A picture from my life:

Lots of restaurant and cafe restrooms have this extra lock, especially Asian restaurants. Why? Is it because the lock on the door handle breaks too easily? Do I really care to know? 🤷‍♂️

Thing on my mind:

I got “feedback” from a friend this week because I asked for an intro without asking if he wanted to catch up first, and he didn’t like that. We haven’t talked in about a year, but I’ve known him for a while so I didn’t think too much about it. He said that I should’ve known because he’s a relationships-first guy, and maybe it’s true I should’ve known especially because I think of myself as a “people person” so I should’ve been able to discern how to best approach each person.

These things are tricky though. Sometimes I’m on the receiving end of it. People have asked me to catch up, and then I find out they’re just trying to get me to send them to someone else. If I like the person and the reason is a good one I probably would’ve been happy to help over email or a quick call. That’d be way more efficient for both sides. Sometimes when I don’t think I know the person that well, I’d want to catch up first and remind myself why this person is awesome, and if they don’t offer to do that I get a little annoyed. It also depends on timing - sometimes I’m busy and I can’t get back to all the people asking me for help. Other times I feel like my head’s above water and I can take a few phone calls or coffees.

I haven’t done a deep reflection here but off the top some variables are: 1) how well you know the person 2) how fresh is the relationship 3) do you have a personal interest 4) what’s the objective of the meeting (eg quick intro, catch-up or a deep-dive on strategy) 5) what method of connecting is best for the objective (eg two friends catching up is probably best done in-person) 6) how well you can communicate the objective without warming up the relationship 7) what the person prefers 8) what you prefer 9) how well you can communicate your preferences, etc. There are probably a lot more variables and that makes this a pretty complicated problem. Some people have strict policies like only email or only calls, but if you want to do that you’d need to get comfortable making, say, a big investment decision over email without ever meeting the person. Some people like Mark Cuban can do that, but it requires work and probably lots of trial and error.

Piece of content I recommend:

I coached 101 CEOs, founders, VCs and other executives in 2019: These are the biggest takeaways by Leo Widrich

Helping founders is mostly playing therapist (or “coach” if you’re too alpha for therapy), but not everyone does it well because they haven’t been in the shoes of a founder or they just don’t have the right kind of empathic powers. Based on this essay I think Leo Widrich has found his calling. Some quotes I loved:

What I’ve learned is that most of our problems occur when we don’t see our own power anymore.

The question I often like to ask then is: What do you have to accept to step back into your power in this moment/relationship? Frequent answer: That the answer might be “no”.

Whether it’s fear, anger or hurt, what I started to practice with my clients is to let these things come and as they come, notice how they don’t want to stick around if we really agree to them:

  • The sadness wants to become tears and flow and become tender thereafter

  • The anger wants to punch, ball hands into fists and then fizzle out through the arms and legs

  • The loneliness wants attention, to be held, embraced and just sat with.

  • The fear wants to be felt, receive attention and permission to flow through the body, only to leave a trail of energy and aliveness behind.

Enduring gets us far, but I don’t think that’s what life is for. To let go of that belief and to allow a new one to emerge, often one rooted in love and joy, is scary and takes courage. Especially when endurance has helped you build a massive company or another successful thing.

As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My latest essay is called From Socialcam to TikTok: How we figured out video social in a decade