Business Mistakes: 5 Things I’d Do Differently if Starting Over in 2024

By Sean Ogle •  Updated: 08/15/23 •  10 min read

In my 10 plus years of running Location Rebel, let’s just say I’ve made a lot of business mistakes.

Wait, hold up.

Did I just say ten years?

Why yes, my astute friend, I did. And if we’re counting, it’s actually been thirteen years.

Damn, I’m old.

But Location Rebel has brought so many opportunities to my life.

It’s sent my life down a path that’s been much more fun, fulfilling, and profitable than I ever could have imagined.

Ah, yes, that’s more accurate.

For the past week, I can’t tell you how long I’ve hovered over this post. Not sure what to write.

I could do a sappy and generic thank you (but seriously, thank you!), but that didn’t seem valuable enough.

Instead, I’m reflecting on 5 of my biggest business mistakes.

These are the things I would have done differently looking back, and with each of them, I try and provide some lessons on how you can avoid making the same mistakes and what you can do this week to make positive progress on your own ventures.

How You Can Avoid My Biggest Business Mistakes

Mistake #1: Not Spending Money on Advertising

I’m going to let you in on a really embarrassing secret.

This site?

It’s not nearly as big as you think it is.

Our traffic numbers have been more or less stagnant for the past few years. I haven’t put a ton of effort into changing that, being mostly focused on the YouTube channel and making sure academy members are happy.

But here’s the thing.

I do a lot with the traffic I have. I’m very good at building relationships with readers. I’m very good at converting email subscribers into customers. And I’m very good at getting results for the people who do decide to join our community.

I’ve got the hardest part figured out.

Yet, when it comes to traffic, I’ve just continued to create more content and hoped it would rank without being more proactive about it (until recently).

A while back, we ran ads for a couple of weeks. I spent around $750 to get 500 new sign-ups.

At least 10 of those (I think) can be attributed to new Location Rebel Academy members.

That’s over a 500% return on investment.

Traffic is one of the easiest problems to solve because you can pay for it through ads, or any other number of channels.

And the times I’ve done it? It’s worked.

There’s a long story about why we stopped, but my mistake is not making this a priority years ago.

Once I knew I could return positive ROI, there’s no reason not to grow our presence through the use of ads.

What Should You Do?

If you have an online business, create and test your product funnel as early as possible, and run ads.

Look at all of the biggest online marketers out there. Did they wait and spend years building an audience organically? Nope, they spent on advertising, and now many of them have followings just as loyal as we do here.

Obviously, there is more to it than just throwing money at ad spend, but with testing and a willingness to learn, it’s the fastest way to grow any online business.

And if you’ve got a good funnel? Amazing things will happen:

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Mistake #2: Not Focusing on SEO from Day 1

Many of you know that my “bridge business,” or the way I transitioned from my day job to a full-time online business, was in part from doing freelance SEO.

I was good at it, and I got some big wins for the people I worked with,

But you know what I didn’t do and what took way too long to do on this site?


I even told new bloggers, “Don’t worry about SEO when you’re starting. Focus on quality content and building your audience.”

Quality content is important, but it means absolutely nothing if people can’t find it in the first place.

For the better part of 5-6 years, I really didn’t do anything to optimize my blog content.

Fortunately, I got lucky and still had a few posts take off, but the majority of it? Crickets.

When you don’t do that, you’re forced to spend a lot of time, effort, and money to go back and do it all after the fact.

I’m right in the middle of this now.

Here’s an interesting fact for you.

Out of around 700 blog posts on this site, around 150 of them haven’t received a single view in the past 3 months.

Not. ONE.

Many of these posts didn’t stand a chance, regardless. They were poorly written, outdated, or irrelevant.

But others are good. The concepts are good. But because I didn’t have a plan for promotion or optimization, they languished in the dark recesses of our archives.

As I mentioned above, ads are great, and they can fast-track a lot of growth.

But even better than that? Consistent, free traffic that solves a problem people are looking for.

What Should You Do?

Whether you have an established website or are just starting, here are a few things you should do on every post:

  1. Create a lot of useful content
  2. Choose a searchable keyword and include it in your title, H2 tags, and in the body of your post
  3. Install Yoast or Rank Math on your site, and fill out fields for Title, Description, Keyword, and Social.
  4. Include images and fill out the meta tags
  5. Look at “related searches” in Google, and include relevant keywords in your post
  6. Go back to relevant old posts on your site, and link your new ones.

Check out this blog audit which will help you assess where you’re site is as a whole.

If you’re wanting to take SEO seriously, then a tool like SEMrush is a game-changer. Here’s my full SEMrush review.

And here’s how I’d do keyword research to figure out what to write.

Mistake #3: Not Being Consistent With YouTube

I’ve always thought most bloggers should have two platforms they focus on.

Your website, and then one other thing.

Maybe it’s Instagram, maybe it’s TikTok, maybe it’s a podcast.

For me, YouTube has always been the preferred platform.

I enjoy doing videos, but unfortunately, over the years, I haven’t been consistent with it.

I started a vlog of sorts when I was living in Bali.

Then I started it again in 2016.

Then I did a daily vlog for a month and gave up on it.

I don’t do videos to become a “YouTuber.” Sure, it’s always nice to see comments, likes, and shares, but the real reason I do videos is that it’s the best way for my audience to get a sense of who I really am. It’s the easiest way to build trust and show that I am who I say I am.

BUT, I wouldn’t argue if each video I created did bring in more people to Location Rebel.

I put up my very first video in 2009. It took until 2020 to hit 20,000 subscribers (which was pretty awesome).

But since 2020?

I really got focused on YouTube and put a lot of videos out nearly weekly over the last few years.

The result?

It took eleven years of inconsistent posting to hit 20,000 subscribers. And just about three years of consistent work to more than double it.

That shows you the power of consistency.

What You Can Do?

Regardless of what the second medium you use to grow and promote your brand is, stick to it. I often would make it a few months, not see quick results, and then move on.

But if you’re consistent, continue improving, and take it seriously, any medium you choose (Podcast, Video, Social, etc) can make a huge difference.

Mistake #4: Making Personal Development an After Thought

When I say “personal development,” I don’t necessarily mean this in the woo-woo sense you often see in entrepreneurial circles.

I’m thinking more basic than that.

Healthy routines and habits.

Eating well. Drinking less. Exercise every day. Reading on a regular basis.

The small things that we all know we should do, yet often have a tough time implementing over the long term.

I’ve said repeatedly that the best thing I can do to grow my business is to improve my health and my mindset. Those things mentioned above are exactly what I mean.

I’ve also come to terms with the type of business I want to run. There are 3 different types of entrepreneurs, and I’m a “Freedom Fighter.” Recognizing that can help me to not beat myself up too much about deficiencies and stay focused on what’s important to me.

What Can You Do?

I wrote this post years ago as a bit of a reminder to myself to get back to basics and focus on the fundamentals.

Every time I find myself in a rut or need a kickstart, I go back to these essential aspects of life, and within a couple of days, I start feeling better, which in turn allows me to perform better.

Mistake #5: Not Enough Experimentation

Finally, if there’s one thing that remains constant, it’s that the online landscape is always changing. Different types of business work and then don’t. Different marketing techniques work and then don’t.

And if I were going to back and do it all over again, I’d spend much more time testing, tweaking, analyzing, and improving every aspect of our site and business.

I’ve fallen into a routine of “good enough.” The marketing is good enough. The blog posts are good enough.

But they could be much better. And by not trying to improve upon the things that are already working well, I’m doing both myself and our readers a big disservice.

What Can You Do?

One of the easiest ways to experiment is to start with some basic split tests and test out different forms of marketing to grow your email list.

Every time I refocus on this, I see a nice big boost, and as you begin to find things that work, you can optimize and make it work even better.

Thank You!

So there you go. Those are 5 of the biggest business mistakes I’ve made in over the last decade-plus of blogging.

If you’re looking to go the self-publishing route rather than the blogging route, then I’d learn from these 10 Kindle mistakes.

And if you want to get out of a freelancing rut, I’d check out these freelancer mistakes.

These years have been more incredible than I ever could have imagined. The people I’ve met, the relationships I’ve built, and the success stories that have come out of Location Rebel have left me feeling so fulfilled and happy with the work we continue to do.

I’m working harder than ever to continue improving the site and to help you with your goals. So if there’s ever a way we can help you with your goals of making a change in your life or starting a business, please reach out and let me know.

Here’s to the next decade!

Want help building a sustainable lifestyle business of your own? Grab our free six day course, and we’ll get you going!


Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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