The Strategic ‘Yes’: How to open doors to unseen possibilities

Hey friends,

2 quick things before we get started – firstly, my team and I are working on a new tool to make it easier for content creators to brainstorm fresh ideas and turn them into first drafts. We’re looking for 50 beta testers. Please click here if you’re interested 🙂

And secondly, we’re hiring 🙂 We’re looking for two full-time Operations Specialists to join our team. If this sounds interesting, check out this link where I recorded a video with more info.

Anyway, this week I wanted to share a conundrum I often struggle with… In work and life, we’re constantly presented with opportunities – some obvious with a clear path to return, others more opaque where the potential payoff is unclear. How do we decide which ones to say ‘yes’ to?

A few months back, I got a DM from Nathan Barry, the founder of ConvertKit, asking if I wanted to speak at their Craft & Commerce conference in Boise, Idaho. It was a cool opportunity, but one that on the surface, didn’t seem like an obvious win. I wouldn’t be paid, I’d have to fly 16 hours there and back, and it would be a major hit to my productivity. The few days I’d spend there could’ve been spent making more YouTube videos which would’ve added $100k+ to our business revenue.

But almost as soon as he asked me, I said ‘hell yes’.

Why? Based on my experience, I’ve learned that some of the biggest growth opportunities come through saying yes to things that aren’t obvious wins. It’s the “wooden doors” – opportunities where you can’t see what’s on the other side until you put in the effort to knock and go through (I got this reference from an episode of My First Million a few years ago).

The obvious wins more like “glass doors” – you can see exactly what’s there, it aligns with your current roadmap, and the payoff is tangible. Creating another YouTube video or working on one of our paid products are “glass doors”. They’re important, but by nature tend to be more incremental.

Increasingly, I’ve found that it’s the wooden doors that lead to the unexpected connections, perspectives, and realisations that can be real trajectory shifters for your business and life. They can get you out of your existing mental models, which can have impacts beyond what you could’ve predicted.

For example, at the ConvertKit event I ended up:

1. Meeting two awesome entrepreneurs (Barrett Brooks and Darrell Vesterfelt) who my team and I are now working with as coaches for various aspects of our business.
2. Getting a tonne of useful marketing, branding and product strategy advice from other speakers at the conference (who are way better at this stuff than I am) that’ll definitely improve the courses arm of our business – shoutout to Bonnie Christine and John Meese for being insanely helpful.
3. Randomly connecting with Russell Brunson, author of one of my favourite business books DotCom Secrets, hanging out at his company ClickFunnels’ office, and gaining his mentorship on a few different areas I was struggling with.
4. Recording an impromptu episode of the Billion Dollar Creator podcast with Nathan Barry where we riffed on a new structure for our business that feels exciting and aligned with my life vision.
5. Meeting a bunch of people who I’d previously only known through Twitter and Zoom (eg: Justin Moore, Shawn Blanc and others) – and getting some helpful advice about balancing business with family life.

Beyond all these more tangible outcomes, it was also just really fun to hang out with other creators and entrepreneurs, and to talk business and life.

None of those were even remote possibilities I could have predicted going into the event. The potential upside was hidden until I put in the effort to go through that particular wooden door.

And the value has already paid off tremendously. One piece of advice from the connection with Russell Brunson for example, could add millions in value to our business if implemented. It filled in major “unknown unknowns” for me in a way that would have been impossible without that face-to-face interaction.

That’s the nature of wooden doors – you don’t know what’s on the other side until you expend the effort to go through them. It’s opaque upfront, with only the potential for an outsized payoff. But the downside is that not every wooden door will lead somewhere valuable. It’s impossible to predict which ones will be magnitude-changing prior to going through.

When you’re just starting out, it’s generally useful to default to saying yes to just about everything. Go through as many doors, both wooden and glass, as possible.

But as you achieve a certain level of success, you need a more refined framework for what you say yes to. With so many inbound opportunities, you have to become much more selective or risk spending all your time just opening doors and never actually executing.

My current framework for saying yes to the right opportunities:

• Does it energise me or will I dread it?
• Could it potentially lead to new relationships / perspectives / realisations?
• Is the asker someone I want to build a relationship with even before knowing the full outcome?

If I get two “yes” signals out of those three, it’s likely worth pursuing the opportunity. Even if I can’t see through the woodwork, there’s potential upside that can’t be predicted or quantified upfront.

The key is that for any yes, even on a wooden door, you have to commit to showing up fully. Relentlessly building relationships, asking for advice, gaining new perspectives. That’s what unlocks the potential value on the other side.

So while consistency and focus are critical for any creator business, don’t discount the overlooked opportunities where the payoff isn’t immediately obvious. Say yes to some strategic wooden doors, expend the effort, and you may be surprised by where they lead.

I’d love to hear from you – what’s an example of a wooden door you walked through, where the outcome on the other side was way better than you could’ve predicted? Please do hit reply and let me know 🙂

Have a great week!

Ali xx

❤️ My Favourite Things this Week

📚 Book – Simple Marketing for Smart People – Released this week by my friends Tiago Forte and Billy Broas (both of whom were internet friends for years before we met IRL). I had the honour of writing the forward for the book when it was in draft format, and I’ve been enjoying re-reading it to remind myself of the key lessons and to realise: “damn I really should be implementing more of this advice lol”.

🎙Podcast – I absolutely loved this conversation between Andrew Wilkinson and Jason Fried on Andrew’s new podcast, Never Enough. I’ve been following both on the internet for 10+ years, and vibe with both their philosophies around business. Jason’s take on anti-goals, building businesses slowly, focusing on profitability and enjoying the journey have especially resonated with me over the years, and formed the basis for a lot of my own perspectives on business and life.

📚 Book – Getting Things Done by David Allen – This is probably the most iconic productivity book, first released in 2001. I’ve read it a bunch of times over the years, but I’m doing a re-read to (a) remind myself of the key ideas, and (b) apply the 5-step GTD method to the current projects and tasks in my business and life, which are quite different to what they were last time I read it. With a few more years of experience under my belt since the last time I read the book, I’m finding new insights that I totally missed (or didn’t appreciate the importance of) the first time around. In fairness the book is a bit of a slog to get through, with lots of things to action, so I’d consider it more like a textbook to study “properly” rather than a casual book to read cover-to-cover. At least that’s how I’m approaching it this time around 😊

📺 TV Show – I don’t normally watch TV shows. In fact, one of my rules for myself (which I’ve had since med school) is that I don’t watch TV on my own. This year, in honour of the fact that I’m now a 30-year old man, I’ve decided to make an exception when I’m on planes. So over the past couple of months, when I’ve been on United flights, I decided to watch *The Last of Us.* My goodness, it’s incredible. I’m around 7 episodes in (so please, no spoilers) and it’s the most I’ve enjoyed solo screen time for a very long time.

🎥 YouTube Channel – I’ve been a recent binge of Alex Hormozi’s latest stuff. I used to watch him a lot last year, and then a few months ago his content shifted to more ‘generic’ stuff and away from ‘business’ stuff, and so I stopped being interested. Turns out he and his team had this feedback from hundreds of entrepreneurs, so they’ve recently done a pivot and gone back to straight-up business educational content. And it’s been ridiculously useful – Alex seems to be uploading videos every single day, and they’re all insanely useful if you’re growing a business. My team and I often send each other the videos, only to find the reply is “yep just saw that this morning, it’s a banger”. If you’re an entrepreneur (or an aspiring entrepreneur) and you’re not already Hormozi-pilled, Alex’s channel is one to have on repeat on YouTube 😃