Start Now, Suck Later: What I’ve Learned Since Finally Hitting Publish
How one scared-to-commit dude went from overthinking his newsletter to making it the best thing he’s done all year.
Haven’t we all thought about starting something and just stayed in the planning phase because planning is easier than doing? No? Just me? I’m the only one? Ok, Substackers, we know that isn’t true. 🙂
That was my exact experience with this newsletter.
I’ve always known I needed something, I even dabbled with a few different things: a section in our company newsletter, some longer-form content on other platforms (Facebook performed the best, followed by LinkedIn, then all the rest for medium-form written content, by the way). But I kept saying, “I know I need a newsletter... I know, I know.”
But I never started.
Looking back, the thing that held me back most was fear of commitment. I’m not someone who usually starts and stops things. I try to do a few things well, and when I commit, I really commit. That created a kind of resistance. “Do I really want to write all the time? How many times a week should I post? Should it be on Mailchimp? Substack? Something else?” (Shout out to Joe Manning for pointing me in the right direction. Substack has been amazing. More on that later.)
Then I finally said, “OK, it’s time.” I got started. And wow, what a ride it’s been. Here are a few highlights:
Writing has been (mostly) amazing.
The exercise of writing has been amazing. There are still times when I think “I have no idea what to write about today,” so I just bang on the keyboard like an over-caffeinated gorilla for thirty minutes without much to show for it. And I have had other sessions where my fingers can’t keep up with my brain, and the words are just pouring out. I don’t love the gorilla sessions, but the can’t keep up ones are pretty amazing. I find writing things really helps me organize my thoughts. I have to lay them out in a way in my mind that I can unpack and explain them so it becomes this great feedback loop where I can better understand my own thoughts on a topic or situation. Even if you never publish, I think starting a journaling or writing practice could help anyone organize their thoughts, and you’d be better for it.
You can’t predict a banger.
I’ve written some that I think “ooooeeee… I’m ‘bout to break the internet,” and I’ve written others that I think are good but just more basic. And the break the internet one gets some interest, but not much, and the more basic one, people “love”. This isn’t about “going viral,” this is about developing an audience and regularly sharing your thoughts, views, and such with them. Don’t worry about the likes and restacks, just write for your people, the rest will take care of itself. Looking back, my best ones are probably ones where I am just “talking to my tribe” without much in the way of editing or trying to “make good content”. The only caveat to that is timely publishing. When there is a big economic headline or real estate headline, and I can crank out something overnight, those are always the best performers.
Learning lesson: speak on the headlines.
There is a learning lesson here. I know I have said this in many of my articles, but the power of publishing a timely, thoughtful opinion on a big headline works. Period. So why don’t we do it more? Why are you not being the voice for your sphere of influence for real estate or mortgage? In this rapidly changing environment of consolidation (hello, Rocket and Redfin), consternation (every headline seems bad right now), and chaos (more people are confused than ever), there is a hunger for a voice to help it all make sense. You might not be able to be that voice for million or even thousands of people, but you damn sure can for the hundreds in your life who already know you, trust you and love you. Please start here.
Consistency wins, every time.
A lot of people have started an email newsletter. Some people have even kept it going for a few weeks. Very few keep it going for a few months, and almost none will keep it going for a few years. THAT is where the magic is. I am still at the beginning of my journey with a lot to learn, but I promise that in two years, you’ll still be getting my brain into your email inbox. It isn’t easy to come up with a minimum of two pieces per week. Start. Never stop. And you will win. You do need to decide if writing is “for you,” but after that, just know it’s a part of your life on a daily basis, and you will win because almost everyone else will quit, most of them really quickly. Plus, you also train your audience to look for it. I had a few people email me saying, “When are you going to write about (blank headline)?” Those are the things that tell me this is working, and I am finding my tribe. Your business is no different.
Freedom to create.
This one for may be less enticing for my 1099 crowd since you’ve got a lot of freedom (I’ve even written about how that is part of the problem here) but for me as a “corporate guy” a lot of what I have to do is through other people, building consensus, meetings, committees, etc. My email newsletter is just that: mine. It’s rare to have a place in one’s life where you can be the shot caller, sole decision maker, and arbiter of all things. If I decide I don’t want to write about something, I don’t. If there is a topic I’m passionate about but not everyone else is (10-year treasuries and mortgage rates) I’m going to write about it. Everyone won’t dig it. Some will move on. And that’s ok. But the ones who stay are here for… well, me I guess. And isn’t that what we all want in this business, a group of humans who will show up for “you”?
Substack is lit(erature).
I freaking love the community at substack. Maybe its because it started as a sort of writers forum, and when you put your personal writing out into the world, it is a little scary, but dang it if people are kind, thoughtful, nice, willing to share, willing to debate. It reminds me of old school Facebook days, but with a lot fewer photos of people’s breakfast. Again, I don’t know why, and I kinda don’t care. I just know I am enjoying the experience over here quite a bit.
To wrap it up:
Writing is good for your soul, try it.
Don’t chase viral, just make cool sh*t.
Consistency is a superpower.
Freedom to create is a blessing.
Substack is lit.
So, what have you been thinking about adding to your life, personally or professionally? What’s holding you back?
Is it time to get out of the planning phase and into the doing?
For me, starting this has been the best thing I’ve done in 2025. Not just for my “brand,” but for my heart. Reconnecting with people. Getting my thoughts organized. Sitting down to write about what matters, it’s done more for me than I expected.
Let me know what you’re thinking about starting. I’d truly love to hear.
-k
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Great post—appreciate the nudge. I agree that if you want to draw readers in, you need to be timely and take a stand. That’s what starts conversations, and in a world full of noise, conversations still matter.
Back when I was developing STEM/STEAM curriculum, I blogged regularly and built an international audience. People sought out my perspective because it was rooted in both experience and thought leadership. Real estate has been a different story. I find that the more academic, reflective tone I naturally use doesn’t always land in an industry that leans toward flashy, fast, and formulaic. Still, I’ve come to see that there’s a place for depth—it just might not look like traditional blogging.
Your post reminded me that maybe it’s not about changing what I say, but exploring how I say it, and to whom. So thank you—for the encouragement, and for helping me rethink my approach without losing my voice.