Why Giving Grace Makes Us Better Entrepreneurs

How Reserving Judgment of Other Entrepreneurs Makes Us More Successful | Greatest Story Creative

We’re back in part 3 of my 5-part series, “Being Human in Business.” Our work is about looking at how recognizing our humanity (and others’ humanity) makes us better in business and better members of our community.

My inbox overflowed last week with a tremendous amount of support and stories in response to Part 2 - my post about secret struggles. If you missed it, I shared my personal struggle of facing infertility.

In response, I heard a lot of “me too’s.”
I heard a lot of “this helped me” and “you’re not alone.”

I heard stories not just about having children, but about personal grief, depression, managing a family, death of parents, and other things that touch us or the lives of those we love.

And I can tell you, just one email would have made it worth it to share, let alone the dozens I received.

So if last week was about realizing that we all fight personal battles and that you’re not alone, this week’s story is about realizing it’s just as important to give grace to others who are fighting their own more public, business battles.

In today's story, we'll look at:


The thing is: it’s easy to judge. It’s harder to empathize.

This story’s been sitting in the back of my brain for awhile. I go to networking events from time to time. Occasionally, I meet people who I realize I have a mutual friend or connection to.

Here’s what’s happened to me multiple times when, through chatting, we’ve identified a mutual connection. I hear something like this,

“Oh Gary, OY yeah he’s rebranded a million times!”

The underlying message: See - Gary has no idea what he’s doing! Can you believe it?

Yes, I can believe it. But why are we coming down so hard on Gary?

Look, branding and business aren’t easy. Both often require skills that don’t come naturally even to some of the best and successful entrepreneurs. I help small business owners create brands from their story or rebrand based on their story. And I know from nearly four years of this work, how incredibly hard it is to brand yourself well - let alone run a business.

Getting really specific on branding, I’m not surprised sometimes when I see other business owners try to reinvent themselves through a rebranding process multiple times. It’s an example of how iterative the process of being an entrepreneur is.

We all have paths to walk as business owners. Sometimes it takes trying on a few stories, a few brands, a few ways - to find what fits us best. And even then, businesses and business owners will always change and grow over time.

I know Greatest Story isn’t the same business it was in the fall of 2013. It’s not even the same business it was last summer at this same time!

This consideration is one of the biggest reasons I try actively not to give brand feedback to an entrepreneur without asking them about their logo and website first. I want to understand their goals and their business better - because those things inform how strong or not strong their brand materials are.

I can’t know the whole story just by looking, and neither can you.


In the spirit of community over competition - creating a community where it’s safe to try is the only way we thrive together.


So the question I put to you is when you see another business owner who is trying something (a rebrand, a new business idea, a new presentation) - what will you do?

Will you…

  • Be confused - how can they be trying something new yet again?
  • Give it a chance - maybe this is something great this time?
  • Remember how hard this journey is for all of us, extend grace and offer your support?

When you do the latter things, you help create an environment - an entrepreneurship community - where it’s safer to try new things and test out new ideas.

And what is entrepreneurship if not the testing and trial of the new? Creating something from nothing? When the environment is safer to try, it’s safer for you to try too.


As business owners, we live a degree of both our success and failure in public.

There will always be side conversations and head-scratching moments. “Why are they doing that? It makes no sense to me?”

We all know that people are watching and there will always be those who don’t get it. 

But whether or not you get it - that’s not the point. The point is - are you leaving room for others to find their own path, even if it’s not the path you’d take or the process you’d take to get there?

If you do one thing today, I’d love to encourage you to support 1 business owner in your circle that you haven’t understood well and:

  • Ask them a 1 on 1 coffee
  • Attend their new workshop
  • Go to their website and read their about story

What can you do to better understand someone who has you scratching your head?

My bet is that the better you get to know that person, the more understanding you’ll gain and maybe you’ll even find common ground and a new, stronger connection to one another.

Looking to next week for “Being Human in Business”

Today, we looked at giving grace to our fellow business owners in their branding and business moves.

Next week, we’ll take it further and I’ll show you some of my best practices for building relationships with other entrepreneurs and referral partners!

Til then, what questions do you have about being human in your business? I’m here for ya.

Further reading: