Dear Diary,
Tom here. Sheesh. It's been a while, eh? I guess it's time for an update...
It's been close to a year since I last posted an update on this blog.
How is that even possible?
Time flies, I guess…
So you might be wondering:
Questions. So many questions. Some are even good.
So here’s the deal.
Over the last few years, I’ve been deep in the trenches, creating and launching products and growing an online education business (among other things)...
My focus for the last couple of years has been to build a business that can live and grow on its own and without my name all over it. I designed this business intentionally so as to avoid creating a 'cult of personality' type business (that, while clearly profitable, always rubbed me the wrong way).
I'm several years into this "quest," which has taken increasingly more time and effort than I expected (but also did kind of expect, if you get me), and I'm pleased to say it's doing well, we've built an engaged subscriber list of approx 50,000 readers, and have served over 70,000 customers worldwide...
…yet in spite of this progress, I still have "promises to keep and miles to go before I sleep" and the journey is far from over...
And so I'm writing to share an update on where I've been, and where I'm planning to go moving forward (in business and life, as well as with this blog and the newsletter).
I think there may be a valuable lesson to share here, so let me start at the beginning...
When I started this blog in 2012, I didn’t really have a plan.
I just wanted a place to share my ideas on life, work, and things that I found interesting. A "dear diary" if you will (haha, get it?).
I published unapologetically for myself, NOT for others.
I didn’t expect anyone to read what I wrote.
But, they did.
And, eventually, my ‘dear diary’ became less for me and more for others.
Soon, my blog, podcast, and newsletter became a place for others to find useful training, tools, and resources to help them achieve their goals (and overcome the army of bad habits and destructive self-talk propaganda that keep so many of us dormant, stagnant, and stuck).
So I decided to keep doubling down in this direction; writing about things that I thought would help the greatest number of people, on the subjects I cared the most about.
(and yes, that was the full extent of my ‘marketing plan’)
Slowly but surely, I attracted new readers and subscribers. I did it all for free, spent thousands of hours on it, and made no money from it.
Of course, "free" is not sustainable, so I embarked on a new quest...
Quest #1. I wanted to replace my income from the military with my writing and publishing work.
I resigned my commission as a Captain in the Army in 2013 (making somewhere around $50 or $60k a year if I remember correctly) and replaced it with a $0/year income as an “entrepreneur.”
Basically, I jumped and then had to build the plane on the way down, so to speak…
My thinking was that if I could replace my previous income with the profit made by creating and selling digital products on my site, I could continue to do this "thing" that I was doing (and, ipso facto, avoid becoming a wage slave).
Fortunately, I reached that goal by the end of 2014, which gave me the runway I needed to keep going.
So I set my site on the next summit...
Quest #2. I wanted to hit that elusive 6-figure mark (annually).
According to a few random business and market reports I found online, only about 10% - 15% of small business owners earn more than $100k per year. Therefore, breaking that number would put me in the 90th percentile of entrepreneurs.
A good challenge.
I felt like if I could earn at least that amount on my own, through my own creative effort, I could consider myself a “legitimate tough guy” (see page 20 of The Art of Instigating -- hat tip Vin Diesel from “Knockaround Guys”).
Through a combination of my own writing and publishing, as well as consulting with brands to help them increase their traffic, subscribers, and sales (and earning a small percentage of the revenue I helped them generate), I crossed that threshold in 2015/2016.
This was a major milestone for me.
It provided the validation that my monkey brain needed that this “thing I was doing” could be sustainable and that I could keep doing it (despite my Dad's plea for me to get a 'real job')…
…yet, it was also a double-edged sword (as success often is). In this case, the other edge of that sword meant bigger, more ambitious dreams, desires, and pursuits.
Needless to say, I set off on a new journey...
Quest #3. I wanted to build a “proper” business
By “proper” I meant an enterprise with more people than just me and a VA, and likewise: something that provided a bigger impact and delivered bigger outcomes for a greater number of people than I could on my own.
Ideally, this "something" could one day run itself or be sold for a profit.
After a few fits and starts, including growing an agency to multiple 6-figures per year (before shutting it down...a story for another time), I finally got something off the ground that worked (and met all my above criteria).
A few years later, we reached the "important revenue goal" and now we have what some might call a proper business.
That's cool because, statistically, close to 90% of small businesses fail after 5 years...
(so again, hitting that 90th percentile, which I'm a big fan of)
What's also been a great experience is building a team and increasing our scale of impact.
Building a team is challenging. People depending on you so that they can put food on the table is even scarier. This is why it's so meaningful to me that we are able to give our team the ability to work for an amazing company on an important mission (no corporate BS, we're not funded by Blackrock so I don't have to force people how to "think right", and because I'm bootstrapped, I don't have to bend the knee to anyone -- we can focus entirely on serving our customers, clients, and team).
I'm proud to say everyone who has joined our team since the beginning has stayed with us -- and I'm hoping for another decade or more of continued success.
With that said:
And of course, the higher heights you reach, the greater the fall (if you fall)...which makes the 'fear of failure' that much greater.
So while it’s not all Bugatis and bling (more like diapers and a 401k), we now have a substantial asset/entity/enterprise that can make a meaningful difference in the lives of people around the world.
It also means...
And maybe most importantly of all:
It's proof that with the right mindset, dedication, and a pinch of audacity, it's possible to turn your creative or entrepreneurial dream into reality.
(if my attention-deficient, cave-man brain can start with nothing and bootstrap to success, I have to believe it's possible for just about anyone to do it)
Waaaaayyyyyy back in 2014, I wrote a blog post called “The Entrepreneur’s Journey." In this post, I wrote about how I envisioned the pursuit of anything creative or entrepreneurial.
I depicted this journey in a classic fantasy format (because -- paraphrasing C.S. Lewis -- sometimes fiction can be "more true" than non-fiction because no one can be deceived by it).
I was so into the idea of it, that I even ‘illustrated’ what that journey looked like in a PowerPoint slide (just Tom being Tom, investing an absurd amount of hours into the "important" things 🤣)…
Long story short -- in an unintentionally prophetic way, my story + illustration about “The Entrepreneurs Journey” ended up being accurate.
In particular:
Once you've conquered one summit, it's natural (dare I say: automatic) to set your sights on the next summit...
That desire for the ‘next great height’ I believe is in all of us -- certainly it's in the heart and blood of creators and entrepreneurs…
And that’s why I’m writing this today.
I'm fueled by the desire to push further and to ‘test my chops’ in this next phase of work, business, and life...
But I've changed...
My thinking has changed...
The world has changed...
And the things I'm "up against" now are bigger and badder than before...
Bottom line: this path I'm walking is very different than what came before (with a lot more riding on it than ever before).
So I say this with some trepidation around this next phase of life...this next quest, this latest pursuit, this new height in front of me...
Just because I haven't fallen doesn't mean I won't. This is the everpresent reality of business, writing, and life in general ("nothing gold can stay" and all that, since we're getting poetic in today's blog post)...And while I think somewhere in my heart I was hoping to someday be completely over that "fear" of failing...
...the reality is that even with experience, wisdom, and a "track record" of success -- it still feels like I'm at square one...
Which leads me to...
Quest #4. What's coming next...
Over the coming months, my hope is to reignite this blog and my newsletter with a renewed sense of purpose and what I hope is a wealth of lessons learned from my last decade "in the trenches"...
I want to share the good, the bad, and the ugly; what's working and what's not, based on real-world experience...
And I'm also interested in exploring new projects and ideas, like how to use an "A.I assistant" to create simpler and more profitable businesses (especially for solopreneurs and those looking to stay lean/agile), how to tell meaningful stories (that attract readers, customers, and clients), and more...
BUT! -- I only want to share what's useful and meaningful for YOU.
Since I'm over the need for an online 'dear diary' and this blog/podcast/newsletter has served its purpose for me...unless what I write is useful to you, I might as well shut it all down.
And that may be what I do.
But before I metaphorically "nuke the site from orbit," I want to hear from YOU!
What do YOU want me to write about?
What do YOU want me to share, teach, or explore?
Leave a comment below and tell me what would entertain or inspire you? What would make you come back to read my next blog post or newsletter?
For those who have been following me for a minute; what has kept you coming back all these months and years? Or what would be “Tom returning to form” for you?
All ideas are welcome.
Even the crazy ones.
(post anonymously if you have to, but DO make sure to leave at least one comment!)
P.S. Listen, I know it's 2023, and people don't really comment on blogs anymore. It's likely if this was a TikTok post with me pointing at floating text on the screen while I carefully gyrate my hips to the latest Nicki Minaj track, this would get more views (how couldn't it?)...
...But I believe there's still value in blogging, and there's still a place for long-form content in this world, at least for those of us who can read above a 6th-grade level.
I also believe in the value of being able to have a dialogue outside the policed echo chambers of today's mainstream platform...
Bottom line: I want to hear from you so leave a comment below! Right now!
If you've never commented on any of my blog posts before, make this your first.
And if you're a returning reader; an OG who's been commenting for years -- your feedback is especially important to me and I want to hear from you!
Your words and feedback fuel me, and I’d love some energy moving into the next phase of this journey.
Thanks, and as always: stay frosty.
Last year, I did my first ever year in review.
That was a really fun, albeit time-consuming essay to write...
And this year's year in review (or After Action Review, as I like to refer to it) was no different.
2015 was a jam packed year and 2016 is off to a crazy start, so this essay took me many hours to write.
My hope is that you can learn from my successes and my failures.
But before we get to this year's review, I want to explain WHY I do these.
This essay took a while to write. That said - I'm so glad I wrote it; and I encourage you to review and write down your reflections for the past year.
Here's why:
Bottom line: conducting a year-end After Action Review (AAR for short) is a great thing for anyone and everyone to do. So go, do it now if you haven't (and share in the comments your wins from last year and goals for this next year).
Last year, my AAR consisted of a single evaluation of my entire business / life / projects.
This time, I wanted to give a bit more reflection to individual elements of what I've done, so I'm conducting a series of area-specific AAR's for this past year, and my overall goals for 2015.
I hope this makes it easier to follow and understand what went well and what didn't go well in each area (as well as where I hope to improve)
If you don't know what an AAR is, I explain it in more depth in last years AAR here.
Check that out if you're curious about conducting your own AAR.
For now, just understand that an After Action Review is conducted by answering the following series of questions for a particular event, project, or mission:
Alright, now that admin is out of the way, let's get to it...
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