15 Years of Lessons Learned

These are my 15 years of lessons.

It was worth it.

So during the past month, I’ve been sharing some unique content across my blog, videos, and even podcast to reflect on the last 15 years.

I hit the 15th anniversary of my last layoff on August 18th and then 15 years since the humble launch of jonloomer.com on August 29th.

Consider this the last of that series, but I feel like there are some interesting missing pieces that I haven’t yet covered.

This month has given me plenty of time to think about, not only the celebrations, but the lessons learned and possible regret.

Now, I use the word “regret” carefully. I’m not someone who dwells on mistakes because I’m not sure anything is ultimately a mistake.

We all make intentional decisions that we felt were best for us at the time, and they either were or weren’t. There’s life experience and knowledge and personality type that all help determine the decisions we make.

And those choices will help determine what happened next in our lives, some good and some bad.

With that said, I’d say I have some regrets, but they also have plenty of caveats. I understand why I made the decisions that I did.

And while I might wish I’d done some things differently, I don’t know that those decisions would necessarily lead to better outcomes.

Now, I don’t want to spend this entire episode talking about regret because that just sounds depressing. I also want to talk about the lessons I’ve learned, many of which were related to good decisions that paid off.

So let’s start with those lessons.

First, create without judgment.

Something that makes me a little sad is the number of people I’ve seen give up on their businesses over the years, and I’m mostly talking about online businesses here.

My business was built around content creation, and most online businesses will require some sort of content. It could be a blog, short-form video, long-form video, a podcast, or even building a social media presence.

At least one of those things is going to be extremely helpful, if not necessary, to get your business off the ground.

But the problem is that content creation can be a very lonely place. You see the success stories, and you assume that you’ll be like them.

Comparing yourself to others, especially in the early going, is one of the biggest mistakes you can make.

Something I’ve prided myself on is that I create content without getting lost in the metrics. It’s not that I don’t care about whether my blog is driving traffic, my videos are getting views, or my podcast is getting listeners.

But I know that these things can’t be the primary drivers of whether I keep going. Otherwise, I would’ve quit any of those things within a few months.

The lesson I learned, and I recommend this for anyone starting a new content stream, is to fully commit to whatever it is you’re doing.

Instead of measuring success in metrics, you measure it, at least initially, in whether you completed it.

From the outside, I probably look insanely disciplined because I maintain such a consistent publishing schedule. But I can tell you that I’m not that disciplined.

I’m easily distracted. And that’s why I’m obsessed instead with simply creating the thing I want to create without judgment.

I tend to commit to a content plan at the beginning of the year and then evaluate when the year is over. So I still will ultimately need to determine whether doing that thing is worthwhile and it’s helping my business.

But I don’t let that distract me while I’m creating, or it will be very easy to quit.

Something else I’ve learned over the years is that impact from content isn’t only found in metrics.

When I was publishing a video per day, my metrics never got that amazing. But I’d often hear from people who said they found me from my videos.

And even now, this podcast, at least according to metrics, isn’t breaking any records for listeners. But I routinely get people who book one-on-ones with me or join my membership who tell me that they listen to my podcast, and that’s why they’re there.

That’s important!

The next lesson I’ve learned is to build a weekly routine.

Probably the biggest challenge of running your own business is that you are your own boss. You don’t have to work today if you don’t want to.

And while it’s certainly important to take time off, what you want to avoid is a chaotic approach to your day that has no structure.

For me, this applies both to my content creation and any other task I complete for my business.

Videos on Mondays, blog posts on Tuesdays and sometimes Thursdays, and podcasts on Wednesdays. Strategy sessions and welcome meetings for members on Tuesdays, webinars on Wednesdays, one-on-ones on Thursdays.

And I apply a similar routine to things like tasks around the house and my running routine to stay in shape. I write everything down in a note, and I know what I need to do on a given day.

And to be clear, I was absolutely never like this before, and it took a lot of work to make it a habit.

Another lesson I’ve learned during the past 15 years is that you need to embrace change.

Now, this can be contradictory with everything else I just said, so you shouldn’t be surprised that change is hard for me.

It is very difficult for me to change my routine or abandon something I’ve always done.

On one hand, the relentless stream of new Facebook and Meta ads features and changes were good for business, and I embraced that change.

But what was hardest for me was embracing a required change to my routine or approach.

I spent months and years refining my processes and figuring out what works best for me. That’s why for years, my content focus was based mostly around my blog.

It’s where I felt comfortable. It’s why I was mostly only active on Facebook during the first decade or so.

I’d create a presence on Twitter or YouTube or LinkedIn, but I didn’t spend that much time there. I only created an Instagram account for the ad placement.

But when my business started declining, I realized that these tried and true methods no longer worked as well as they once did.

That’s why, as painful as it was, I got into short-form video. I published a video per day for nearly two years because I needed that level of commitment to be able to fully pivot.

I brought the Pubcast back because I knew I needed to diversify my touch points. But I’m doing it in a way that’s easier for me to create.

And during the past several years, I was confronted with the reality that my focus on remarketing and microtargeting was no longer relevant.

And that may have been the most difficult pivot of all because those targeting strategies were a big part of why my business exists today.

So embrace change or expect your relevance and impact to fade.

Okay, so those were some decent lessons, but let’s end on a couple of regrets.

The first is that I’ve completely lost the network of people who helped me navigate the challenges I faced in those early years. It honestly pains me to admit that that’s the case.

Now, as I said at the top, there are caveats to regrets because I also understand what happened.

I am not a naturally social person, and building and maintaining relationships is not easy for me. I’m the person who goes to a conference, but spends most of the time by myself.

But I did build some friendships and business relationships in those early years, and they’ve mostly faded away.

While there are lots of reasons for that, I have to blame myself. I did not handle things well when things got noisiest.

When my profile was at its highest, I had a lot of people reaching out and wanting something from me. Maybe it’s a humble brag, but I also stopped trusting people.

I realized that every relationship was a transaction, and while that may have always been true, I didn’t like how it felt.

Social media also became toxic before it was flooded with bots and AI, so I’ve reacted by pulling back from interacting with people at all in most cases.

It’s a sad story, I know.

I know these aren’t good for my business or for me personally. I know I need to build and rebuild relationships because you can’t go through these challenges alone.

So one big regret is not doing more to build and maintain relationships over the years.

And the final regret…

My business name.

Jon Loomer Digital LLC.

Recall that I didn’t know that I was starting a business when I purchased the jonloomer.com domain. I still didn’t think I was when I started the Jon Loomer Digital Facebook page.

I only added the “Digital” to differentiate it from my personal profile so my friends knew which was which.

The problem is that when all of this started, I was 36 and I wasn’t thinking about the future.

I’m 51 now, and I know that I won’t be doing this forever.

So, what’s my exit? Do I sell jonloomer.com?

I’m sure I’m not the only one who’s ever been confronted with this, but I don’t see how I could ever do that.

So it feels like a bad mistake that I built a business around my personal brand, and without an umbrella name that didn’t include my own.

Is that a regret?

Kinda.

I also realize that I may not be doing this 15 years later if I didn’t focus on a personal brand. I know that creating a broader brand name that sticks is also no simple task.

What would I call it?

In the end, I sure wish it could have gone down differently, but it is what it is.

So here’s the bottom of the glass.

15 years of experience, starting at 36 and being 51 now, provides plenty of opportunity for lessons learned and even some regrets.

I truly believe that a relentless commitment to creating without judgment and a structured routine are the main reasons I’m still here today.

But that same structure and reliance on consistent processes also made me resistant to change, which certainly put my business at risk.

Ultimately, I’m grateful to still be here to share these lessons with you.

My hope is that I’ll be better about the relationship side going forward, whether it’s another 5 or 15 years.

Or who knows?

Thanks for listening and for being part of my journey.