5 Things I Would Have Done Differently in the Beginning

There is an audio version below.

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Unfortunately, you can’t go back in time and do things differently. And thinking about it, maybe that wouldn’t be a great idea. However, one person’s experience can work in the same way. There are things that I missed when I started the journey to create a life of freedom. I know there are many reading this post that have just started or will start their journey. I hope this post helps you avoid the pitfalls I and many others have gone through.

The early days of my dream-chasing journey were filled with wasted time and money. I spent most days not knowing what to do or doing what I saw working for someone else. I wanted this dream to be my reality so badly, so I spent a lot of time chasing my tail. I would see a bright shiny object and hope it would be the thing that brought me income. Here are five things I would have done differently.

I would have focused on building my audience. In the beginning, I was sold on the hype about social media. I did everything I could to build my social media presence but ignored building an email list—big mistake. It took six months to understand that things like social media, Periscope, and Blab are not the best way to build an audience. Those are rented platforms that belong to those companies. Your email list is the people who are interested in what you have to offer and are far more likely to buy from you. Think about the phycology behind who’s mostly likely to buy: The person who sees you mention stuff here and there on social media (the organic reach is limited)? Or, the person who reads your emails, and blog posts? When I focused on building my email list, I had someone to talk to, and a few of those people bought my stuff. Today, 90% of my sales come from my email list. Focus on building your email list-–social media is not enough or the best way to build an audience that can support you.


I would have stop chasing influencers. Just like most dreamers reading this, I had heard the stories—of a person like me—who had noticed something an A-Lister missed, and they helped them. The A-Lister was so grateful they gave the person a shout out. It’s kind of like a Cinderella story if you think about it. The problem with chasing influencers today is that they’re pretty untouchable. Many of them get hundreds of email a day from people who are trying to connect with them as well. Your email or private Facebook message gets lumped in with the rest. My editor at Entrepreneur Magazine made an excellent observation about this. He said when you feel like somebody is trying to connect with you because they want something; you’re kind of repelled. Think about people who want something from you. Think about the old school telemarketer calls or door-to-door salesperson. How did you feel when they tried to sell you? In a way, that’s what’s happening when you’re trying to connect with an influencer. More than that, it’s taking the time you could be using to build your business on your own. It’s a much different dynamic if you build a thriving dream and then connect with an influencer as a friend—not a follower.


I would have waited to spend money. I thought the key to making progress was hiring a coach or taking courses from the big names. I acknowledge I may have found the wrong people, but all I got was surface level content that was designed to upsell me on another more expensive course. There always seemed to be a better version for more money. I spent over $5,000 when the reality was I just needed to build my audience first. I hadn’t done all the work I could have done on my own, first. If I had built an audience and created the offerings, then hiring a coach or taking a course would have made sense. Don’t spend money—not even with me—unless you’re in a place to benefit from the training.


I would have gone after bigger opportunities. For as long as I’ve been doing this, I have thought too small. It wasn’t until this year that I have seen the opportunities far beyond the online space. I have booked several five-figure speaking gigs in other countries, I have book four-figure-a-month consulting contracts, and I’ve had five-figure weeks. We tend to focus on what we know. Realize there’s a whole wide world that extends beyond the same pond everyone in this online space is swimming in. 


I would have taken my business seriously. As the months went on, and the income didn’t come, I viewed what I was doing as more of a hobby. I wish I had treated this as a business and made business decisions right away. I would have been more focused with my time, and I would have charged instead of coaching 127 hours for free. Even if it were $10, at least the people would have had skin in the game, and I would have been making some money like businesses do. I would have thought long and hard about what relationships made sense to my business.

I hope some of the lessons I’ve learned can help you if you haven’t reached your goal of freedom. I’ve been spending some time thinking about what “Lifestyle entrepreneurship” means. At first, I was convinced it’s where those scammy Facebook ads live. But now, I see what it means. Lifestyle business means you create a business around the kind of life you want to live.

It means that you have the freedom and flexibility to live life on your terms while still generating income. It’s not just your life or business; it’s both morphed into what you wake up each day excited to do. To get there, you need to build an audience, create things to sell to that audience, and keep growing. At its base, that’s what this is. There are many moving parts, but they often confuse the bottom line. Don’t get distracted; make your dreams your reality. Keep going.

Audio version: 

What dream are you working on making your reality?

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Photo: Flickr/ Tom Waterhouse