My #1 Biggest Business Regret (and what I wish I’d done differently)

Business regret is a heavy topic. Usually, I like to keep things pretty light around here, but today, we’re going to talk about something a little more serious:

My biggest business regret. 

{cue dramatic music}

And as it turns out, my biggest business regret — which we’ll get to in just a moment — isn’t related to some material accomplishment (or lack thereof), it’s not about a specific strategy I did or didn’t use, and it’s not about a platform or a product or anything like that. 

In fact, my biggest business regret is quite similar to the same regrets that people often have… on their deathbeds.

(THAT got serious fast. 😬)

Let’s talk about it:

In the book, Resisting Happiness, the author, Matthew Kelly, interviewed hospice nurses, asking what their patients had shared with them as they were dying. 

As it turns out, the list of regrets all circle back to just a few key things: misaligned priorities, lack of courage or faith when pursuing dreams, and not valuing and investing as much time and energy into relationships.

Of course, I know we’re all guilty of these things, both in life and business, but today, I want to focus on business (though there’s definitely a life lesson in here, too).

P.S. Would you rather watch the video on this topic? Watch the video here! (If not, keep scrolling and reading.)

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My Biggest Business Regret

When I really think about it, my biggest business regret centers around relationships.

As one of my mentors (and author of The Alter Ego Effect), Todd Herman says “Business moves at the speed of relationships.” I think he’s right.

So, here goes. My biggest business regret?

In the beginning of my business, I wish I had prioritized pursuing more quality relationships with business owners.

Nowadays, I’m proud to say I have relationships with some amazing business owners, and because of that, I also have their influence, perspective, and even guidance in my business. This is invaluable. 

But… that hasn’t always been the case. In fact, in the past, I didn’t give relationships with other business owners a second thought.

As an introvert, I am the last person to go up to someone at a networking event — the last person to reach out to someone I don’t know and try to befriend them. It’s not about being shy, it’s just not my thing. 

So in the beginning of my business, I prioritized other things: 

Creating content (for people to consume when they wanted to consume it)… 

Fostering communities (so people would just come to me and I didn’t have to go out to them)…

Creating online courses (so I could shift away from one on one stuff altogether).

See a pattern here?

So as you can see, I created platforms, but I didn’t connect with people personally.

I grew a following and got to know people from afar, but I didn’t have a ton of true friendships with business owners. 

Which was fine at first, but it became a problem in time.

And if you’re in the same boat now that I used to be in then, then you know this:

You didn’t necessarily get into business because of your dazzling self-accountability. Of course not. You started your business because you had a skill, a talent, a product, or a service you wanted to share with the world — to help the world.  On your terms.

And as an entrepreneur, you don’t have a boss looking over your shoulder. Telling you what to do, giving feedback, holding you accountable. You have sweet, glorious freedom!

Which can be both a blessing…. and a curse. 

Autonomy might be the goal, but autonomy without discipline and without someone holding you accountable can be dangerous.

After all, you know that we really are the sum of the seven people we spend the most time with — for better or worse. If those seven people are… you…. and the echo chamber of your own thoughts, well… that’s not always good. Or sustainable. Right?

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The Importance of Business Relationships

When things are hard, you need the pep talk that you just can’t give yourself. But someone else could — if only they had access to you, if they had a relationship with you.

And when things are great, you need guidance, too. Especially when things are great. This is SO important (and often underestimated):

Author and speaker Brene Brown has said “Joy is probably the most vulnerable emotion we experience in our lives.” 

If that’s true — and I know it is from my own experience — then when things are at their best, that’s when we begin to wait for the worst. In moments of joy, we’re vulnerable, and we can become paranoid. 

We often wait for the other shoe to drop — for trouble to come our way. And if we get tired of waiting, we sometimes go out and find it (#guilty). If you’re someone who has ever self-sabotaged yourself in some aspect of your life then you know what I’m talking about.

In fact, the last time I was guilty of self-sabotage, one of my biz buddies shared that quote with me — the one about the vulnerability of joy. The same one I just shared with you. Full circle. #seewhatididthere

Get the Outside Business Perspective Your Business Needs

So, flying solo is fine, but if you’re in this biz thing for the long haul, you know you can’t — and shouldn’t — do it alone.

You desperately need the perspective that you can only get when other people are close to you and feel like they can share their honest opinions with you. 

You also need the nudge to go further — maybe further than you’d believe possible If you didn’t have someone cheering you on and pushing you past your limits.  

And when you have these valuable relationships with people who are doing what you’re doing — on the same level of ambition as you — you’ll be shocked at how much more you’ll get done, how much more clarity you’ll have, and how many more opportunities will open up for you.

And because relationships are a two-way street, you’ll be able to give back all that goodness when it’s needed.

It’s a win-win. Maybe even a win-win-win. A win-win-win-win-win. A win-finity. Heyyyyy…

Ok, dorky moment over. You’re welcome.

How to Build Valuable Business Relationships

Now, maybe you’re watching this and thinking “Ok, I need more relationships, but where do I get started?”

Here are a few things to consider:

First, I want to clarify that any time you seek to build community and surround yourself with awesome people, that’s good. BUT in this episode, I’m talking about people who are doing what you’re doing. This isn’t about your team, if you have one. They’re great, always actively work to deepen your relationships with your team for sure, but you also need relationships with people on the outside of your business.

Also, I recommend finding a community that requires some investment, like a mastermind or small group coaching program.

This isn’t necessarily about some high ticket thing where you have to spend a ton of money. Maybe. Maybe not. 

But when you’ve got skin in the game, and when everyone else does as well, everyone takes it more seriously, they show up, they participate, they engage, and all of that means you get the help you need. (And you are more motivated to give help, too!)

Free groups are fine for some things, but because they’re free, they’re always going to be a mixed bag. You’ll connect with some people like you, but not always. And data-mining and posting in free groups is never a substitute for forming real relationships.

(🎦And speaking of, if you want my perspective on the pros and cons of paid groups, check out my past episode, “How to avoid shiny object syndrome.”)

Take my free class "The 6-Step System to a Profitable Online Course"

So free groups are ok, but that’s not the best way to build quality relationships, and paid groups are usually a good thing, but there’s one more thing to consider:

I also recommend finding a community where most people have a similar revenue to you and are on a similar level of ambition as you.

It’s ok for a group to have some people who are a few steps behind you… and some people who are a few steps ahead of you. 

For the former, you’ll serve as an inspiration, and you’ll be able to give back. 

For the latter, you’ll see something to aspire to and you’ll get that valuable insight from someone who has surpassed you. 

Just keep in mind that you need a mix.

If you find yourself head and shoulders above everyone else in the community, then you’re in the wrong place.

And by sticking around, you’re holding yourself back. 

Trust me, I learned this one the hard way. I was once in a paid community where I was the only 7-figure earner around. In fact, most people in that community weren’t even full-time business owners yet. 

At first, it felt fun to have all the answers, to be the example to aspire to, and so on. But none of that served my business — just my ego.

When I left that group and joined a mastermind, one where I wasn’t the only 7-figure earner, that’s when my business doubled

Growth was tremendous because I had a group of people on the same level as me, pushing me, holding me accountable, and guiding me through both the bad and the good.

So listen: Your non-business friends are great. I’m sure they love you. But, when it comes to business, quite frankly, they don’t get it. They can’t. And for the record, they don’t need to. Entrepreneurship isn’t for everyone!

BUT don’t let yourself waste away on an entrepreneurial island all alone. As humans, we are created to create, to connect, to collaborate. We’re supposed to be together. And it’s a wonderful thing to be among those who get what you’re doing and where you’re going. 

So, in the same way that you prioritize sales and marketing and customer service, I want you to start prioritizing relationship-building. 

The benefits are real, the ROI is bananas, and if you seek out relationships with people on the same level as you, it will always be a win-win. A win-finity, in fact. 😉

Join the Course Creator Incubator Facebook group for course creators and business owners!

Your Action Plan for Building Business Relationships

I get that relationship-building sounds abstract, so I’ve got two action steps for you to do this week. Today, if you have time:


First off, I want you to start blocking off just 30 minutes in your calendar once a week (though you can do it more often if you wish), and use this scheduled time to be a biz buddy!

But you can call it something less dorky if you want to.

Don’t just think about this and tell yourself you’ll get to it —  I want you to actually block this time off in your calendar and protect it. 

Then once a week, use that time to nurture any biz buddy relationships you have. 

Even if you just commit to checking in on two people, it’ll be a success. Reach out and ask them how they’re doing and how you can help them.

Of course, this isn’t a time to ask for anything in return. Or promote your stuff. Or ask them to promote your stuff for you. 

This is simply a time to show up and be helpful — be a bright spot in their world. By doing this, you’ll develop and deepen a relationship — and you’ll also create reciprocity in the process…. Which is never a bad thing. 


After you’ve scheduled your weekly biz buddy time, I want you to start thinking about joining a mastermind or small group coaching program. The best place to start would be on the websites of those you follow and look up to in the business space. 

If you don’t see an opportunity, don’t stop there. Send them an e-mail and ask for what you want! Often, masterminds or small group coaching programs aren’t advertised or mentioned much publicly (like my group coaching program, Launchpad), but they might still be available through a brief application process.

P.S. If you are a course creator or you want to create and launch an online course, I can help you with that through Launchpad. Follow that link to learn more, apply now, and book a call with me to figure out if it’s right for you!

But whether Launchpad is right for you or not, I still hope you’ll take my advice:

👉 Schedule that weekly biz buddy time.

Even if just for a few minutes, you’ll find it is always time well spent.

👉 And consider plugging yourself into a paid community, a mastermind, or a membership of some kind.

Surround yourself with fellow business owners who are on the same level as you, going after the same things as you. It will definitely help you go further faster.

You might regret some business choices…

But you’ll almost never regret the time you spend nurturing relationships, both in business and life. 


I’m here to help you build, grow, and scale your business.

Check out my show here:


  1. paula

    I LOVE this and agree 110%! In my habit changing and healthy lifestyle course it is ALL about showing up for yourself AND the group. We have group groundrulers on HOW to participate in a dynamic group- most people aren’t trained into it. Accountability partners is also key to my member’s success. Being in a Mastermind group is so very valuable for ME and my business as I am inspired by and inspire my colleagues every day. I hear ya- I’m a bit of an introvert too and it’s super easy for me to isolate and create. Reaching out goes against my nature is EXACTLY WHY I NEED TO….plus it’s more fun. Virtual and in-person meetups are equally as valuable. Glad you brought this up. Paula

  2. Eric

    This reminds me of the African proverb: If you want to go fast, go alone. If you want to go far, go together. Community is vital for us.


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