My simple Wednesday ritual could turbocharge your career

July 3, 2026 — 5:01am

I have this weird little ritual where every week I email someone who’s out of my league, out of the blue. I call this Shoot Your Shot Wednesday (SYSW) and it looks something like this:

The Sunday before, I pick my person from a very long list of publishers, journalists, authors, founders, creators, thought leaders, dream clients, etc. On Wednesday morning at 9am, I draft the most riveting, intriguing, well-researched, personalised email I can possibly write, not a word from AI in sight.

I blast my most upbeat song du jour (currently 12 to 12 by sombr). I whisper “here goes nothing” and press send. I move on with my day.

I’ve been doing outreach like this for as long as I can remember and even though I’ve had countless misses, it’s also generated some pretty incredible results. There was the time I emailed NY-based artist CJ Hendry asking if she would be a guest on my then little-known podcast.

I dropped the name of a mutual friend (her ex-boyfriend, my former housemate) in the email, and my flabbers were ghasted when she responded and said yes. I quickly jumped on a plane and spent two full days in the Brooklyn studio of one of the coolest artists in the world.

Then there was the time I emailed two former colleagues turned founders of Aussie skincare brand Ultra Violette, which turned into an almost two-year consulting project in which I helped launch the brand into 600 Sephora stores across the US.

The idea of pressing send on a cold email makes most people want to curl into the foetal position and shake their fist to the sky.

Through this practice, I’ve won dream clients, landed press opportunities and even made friends with people I previously admired from afar, and it’s no exaggeration to say that it has changed the trajectory of my business and life.

Last month, I shared this concept across my social channels, and it quickly went viral. Comments flooded in from people sharing stories of their own shots taken: “this is how I met and worked with Esther Perel for 2.5 years!″⁣, and “my first New York Times acceptance I sent at 10pm, 3 days before Christmas. I got a quick yes. Just go for it folks!”

I think it struck such a chord because the idea of pressing send on a cold email makes most people want to curl into the foetal position and shake their fist to the sky, but SYSW feels achievable.

It’s one email, one act of bravery, once a week. People also instinctively feel that in an increasingly uncertain world, being brave and creating your own opportunities is the only reliable career strategy there is.

We all have conflicted feelings about doing the hard things in life. Reaching out cold, posting online, having a tricky conversation, setting a boundary, raising your rates, saying no, making an impossible decision – all of these things objectively suck.

But if you want to make them suck less, why not rebrand? Name your terrifying action, commit to it as a weekly habit and ritualise your courage. For example, make posting online TikTok Tuesdays. Make raising your rates Ask For More April.

If you want to become the unapologetic, courageous, bold person you know you can be, you have to teach yourself that the Earth doesn’t stop spinning with a swing and a miss. Your fear doesn’t register in the hearts and minds of people who saw your email and didn’t have bandwidth to respond. They simply don’t care. No one does.

And once you’ve figured that out, you’ve won.

Anna Mackenzie is a start-up adviser, mentor and creator of The Portfolio Career Build Method. She writes a weekly newsletter at annamackstack.substack.com.

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