So heres one of the things that led to this newsletter. Ive been working closely with a few tech/VC brands as part of my consulting practice, and trying to reverse engineer what makes top newsletters and thought leaders in tech/broy realms successful these days.

I realized the best ones are offering what I like to call Male Self Help. Sometimes this is dieting tips and work out mindsets. Sometimes its all the many virtues of microdosing. Sometimes it digital wind downs, putting your phone away at 8 pm.

I first noticed this as a bookseller. Think of some of the most popular business books of late.

Atomic Habits is really male self help. So is Hidden Potential. So is Slow Productivity. So is Super Communicators.

Loads of people have noted that female leadership and productivity books are always put in self help not business. Fewer people had noticed the reverse: That the whole category is turning self-help, no matter the gender or section its in.

I dont talk about this much outside of client strategy sessions, because it sounds like Im making fun of it. Quite the contrary!! I think this is an amazing trend!!!

We have such a crisis of masculinity and leadership and so many people are reaching out for non-toxic ways to live, and work without burnout and ousters.

I think this trend is incredible; its giving people in the tech and start up space in particular research based permission not to burn out; to see their families; to have balance. . .

So part of what I was thinking here with this newsletter was. . . does the reverse of the reverse work?

Like, if business and life hacks and leadership and productivity books are really male self help, and female business books are self help. . . what does a newsletter written with the male self help playbook look like for powerful working women in the second half of life?

Its like how the movie Mean Girls spawned a musical version and then they turned that musical version into another movie.

But heres my problem. Ive been really struggling with: How hard to be on myself when it comes to being healthier.

We all know what to do. And reasons to do it.

And we all know that person who is so obsessed with life hacking that they have no body fat, dont drink, and have sucked a lot of joy out of life. . .

Yes, I want to be a better me. And we are inundated with the joys of being thinner. And I have the willpower to do anything if I care enough.

But you know, I honestly find it hard to care enough.

I work out everyday; I am a great mom; Ive long been a tireless activist professionally for those who need it most for decades; I dont do drugs; I dont smoke or vape; I spend very little time on social media; I dont gamble; Im not unfaithful. I am doing A LOT OF THINGS RIGHT.

And then I think, well I really should . . . how hard would that be?!

Heres what Im going to try: Once a week, Im going to have a SHOULD DAY. This is the day I let myself be a total narc on myself. Ill force myself to do all the things I SHOULD and feel smug for a whole 24 hours. More interestingly. . .do I feel so much better that I want to extend the shoulds to other days? Or is one in seven PLENTY?

Its the reverse of Tim Ferris popularizing cheat days. He gives bros one day to cheat. I give you just one day to engage in allllll the Shoulds. Because you are already doing more hard stuff, I have a feeling, and beating yourself up so much, you should get one unfun day, and six fun days.

Today is my first should day. It is a little hard, because I have my kids, so, lunch, say was not as virtuous as it could have been. . .

But I:

• Didnt eat meat

• Burned 600 calories

• Didnt drink alcohol

• Kept calories under 1200(ish) for the day

• Meditated

I also think you can think about should days in terms of career and life.

I paid my bills.

I pinged my tax people about some unresolved issues.

I had a challenging work conversation.

Its sort of the favors to a future you day. Oh thank God I did that terrible thing on that day I was already sucking things up. . .

I look forward to masking my face, moisturizing my feet, flossing and going to bed at a reasonable hour.