Halftime
The game will last longer than you realize
Aging is relative.
When I was 10, I viewed being 55 as starting the ‘fourth quarter’ of your life. I would retire when I hit 65 (because everyone retired when they hit 65) and spend 10 years in the barcalounger watching football games and puttering around the house.
75 was about all you could expect, at least I thought.
Since then, the average life expectancy in the US has crept up to almost 80 years. I was asking AI about this, at my current age of 55, AI told me I can expect to see another 1-3 years added to my lifespan via medical advances. And another 3-5 years would be added to life expectancy due to advancements in AI.
The advancements via AI are very underestimated, IMO. Sure, there will be some improvements to medicine, AI will eventually reach a point where it can reliably help doctors better diagnose and treat illnesses. And at some point, AI can be counted on to even assist or maybe even perform surgeries outright. All of this could also lead to at least marginal improvements in life expectancy.
The one industry that I believe will be completely disrupted by AI is the pharmaceutical industry. As AI continues to improve and become more robust, AI will likely be able to develop medicines more quickly, and with fewer side affects, logically. I am envisioning a near future where medicine and the research necessary to create new drugs, effectively becomes open sourced. The intellectual, policy, and market restrictions will in great part be lessened or removed outright. Which should, in theory, lead to much more effective drugs coming to market and greatly reducing prices in the process.
Which should lead to more people having access to much more effective drugs that are cheaper, with fewer side affects. All of which will lead to extending lives.
Where is This Going?
My point here is that in the course of our lifetimes, our life’s story is being rewritten in real time. Life’s path that we are walking down is having bricks added to the end of it as we speak.
Living to 90 will become closer to the norm than an outlier within a generation, if not sooner. Hitting 100 used to be so rare that it would get its own mention in the local paper. I think in another decade or two most or all of us will be able to point to at least one living member of our family who is at least 100.
The reality is, if you are in your 40s or 50s, your life isn’t at it’s ‘slowdown’ phase, your life is literally reaching halftime. Most of us will still have decades left of meaningful lives where we work, play and build for ourselves, and our families. This is a big reason why I am focused on helping you understand how to not only grow your Substack, but to grow it into a sustainable business. Because I feel like anyone 40 or over not only has time for that, but should expect that. I don’t want us to think of Substack as simply being a source of $50 or $100 a month. I want it to be large enough to eventually become our main source of income, because it has the potential to be just that.
What Your Age Actually Gives You on Substack
Here’s something the Substack growth conversation almost never addresses: the writers who convert free subscribers to paid at the highest rates are almost never the youngest ones in the room.
They’re the ones with twenty years of scar tissue. The ‘second generation’ content creators. We spent the last 10-20 years trying (some succeeding, some failing) to monetize our Wordpress blogs, our Twitter accounts, our YouTube channels.
Think about what you’ve accumulated by the time you reach your 40s or 50s. You’ve made real mistakes in your field and recovered from them. You’ve watched trends rise and collapse. You’ve worked alongside people who were brilliant and people who were frauds, and you’ve learned to tell the difference. You’ve had your ideas proven right and your assumptions proven catastrophically wrong.
That’s not baggage. That’s the exact thing people will pay to access. When I came to Substack, it wasn’t thinking ‘What should I do here?’, it was more about “I’m going to change what didn’t work the first time. On my website, on MailChimp, on Twitter’.
That’s experience, the type of experience that comes from joining Substack at the age of 40 or 50 versus joining at 20 or 25. And for us, it moves the starting line up. It gives us an advantage that we should lean into.
Substack rewards specificity and depth. Both of those compound with age. The writer who has spent twenty years in a specific industry, role, or discipline has a perspective that is genuinely impossible to manufacture. You cannot fake the pattern recognition that comes from watching the same dynamics play out in twenty different contexts over two decades.
Your age isn’t a liability on Substack. It’s your most defensible asset.
The Real Fear (And Why It’s Lying to You)
The fear that keeps writers in their 40s and 50s from starting, or from going all in after they’ve started, isn’t actually about time.
It’s about permission.
Starting something new at 50 feels different from starting something new at 25. Not being you feel like you have less time, but because the stakes feel higher and the permission feels harder to grant yourself. At 25, failure is a learning experience. At 50, it feels like something you can’t afford.
But here’s what’s really happening:
The risk of starting something real at 50 is not that you’ll fail and waste years you don’t have. The risk is that you’ll spend the next fifteen or twenty years exactly where you are right now, watching the window from the outside, telling yourself you’ll start when the timing is better, when you feel more ready, when movement feels more…sure.
The timing never gets better. The readiness never arrives on its own. The window doesn’t close, but the years go by regardless of whether you walked through it.
You have more time than you think. You have more to offer than you realize. And the readers who will eventually pay for what you know are out there right now, looking for someone with exactly your experience, your perspective, and your willingness to show up and share it.
The fourth quarter isn’t coming for another decade or two at minimum.
You’re at halftime.
And this is a game you can’t win if you don’t play.



I started writing a couple of years ago. I will be 56 in a month. Best decision I ever made. I am building a life I want. I couldn't stop writing for anything.
This is such an encouraging post.
Right to the truth. We have more time than we think, and when we act on these desires time does a magical thing where it stretches, and the mind does a wonderful thing, and gives you ideas. Your brain becomes a beacon that finds ways to refine what you know, and how to say it effectively.