Secret Entrepreneur Struggles - Why There's More to the Story

Secret Entrepreneur Struggles | Greatest Story Creative Blog

When I worked at Disney, one of my favorite things to do would be to have lunch with different people across the company. Over our lunch break where I was feeling stressed and overwhelmed, my friend John told me about the concept of a “worry tree.”

A “worry tree,” he explained, was the notion of a tree where you could write out and place your worries on leaves. Everyone else would leave their worries on it, too. Once you put your leaves out, you were free to take someone else’s in a 1:1 exchange.

But the thing was - when you read everyone else’s, you would always choose to take your own leaves back.

The story here is that we all have things we worry about and struggle with. Given the chance, we wouldn’t trade our worries for someone else’s and - as I’ll share today - we are more compassionate people in understanding what others are going through and the very notion that no one walks around with an empty worry tree.

I’m back this week talking about "Being Human in Business.” In this 5-part series, I’m sharing stories with you about vulnerability in business and how this can be a strength when viewed through the right lens.

We’re going to spend time on this because knowing how to deal with the necessary aspects of being vulnerable will make you a better business owner and strengthen your brand and reputation with others.

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


I’ve thought about writing this article a dozen times over the past few months. It sits in my head, turning over, popping up when I least expect it.

For years, I’ve been dealing with a secret struggle. While my business has thrived, growing year after year. While it may look like I’m doing everything right and can do no wrong, there’s more to the story.

Since July of 2015, my husband Gus and I have been trying to have children.

  • It’s been two years as of the time I’m writing this.
  • There’s no clear reason we’ve identified.
  • We’ve looked at options and continue to, and we have no real answers yet.
  • This has been a hard, unpredictable journey, especially for someone like me who is a planner.

While this does remain a private journey in detail for ourselves and our family and close friends, I share this part of my story with you because it’s important and a part of who I am. It does inform my business. If I am not sharing such an important part of my story, how can I expect my clients to be human and real with me?


Why don’t we share our secret struggles, especially as business owners?

Because we are afraid people will judge us.

I haven’t shared this publicly for so long because I worry about the things we all worry about (especially as a woman):

  • Is it appropriate? Is it professional?
  • What if someone doesn’t want to work with me if I share this information?
  • Will people try to give me advice?
  • I must be a failure because I can’t seem to make this goal happen (and I don’t want people to think that.)
  • And there is no “happy ending” yet to share that would make the struggle story a triumphant one.

We all worry about perception, especially if we have our own business. Some days, it feels like all we run on is perception of our success. We cannot let that fall or the business will fall, right?

Well, after months of having this on my heart, what I ultimately come back to is this:

We have to share our secret struggles because we all have them. We are less alone in our sharing and we are better together.

I’m not planning to share a lot of personal detail on our journey to have a family after this point, but it was important to show you in this context.

Let’s go back to those worries for a minute -

  • Is it appropriate? Is it professional? I’m not sharing all the intricate details, but I am being real about a life struggle that impacts who I am and something that so many women and couples experience but don’t talk about openly. If I share my story, maybe it will make it okay for another entrepreneur to share theirs - what is more appropriate than that for this community?
  • What if someone doesn’t want to work with me if I share this information? Would I want to work with someone who would not want to work with me or my business because I am struggling with something in my personal life and choosing to share it as a way to help others? That doesn’t sound like the right type of client for the work I do anyway.
  • Will people try to give me advice? Yes, of course - probably! Oy. But sometimes it’s a great thing to open a dialogue as you never know how it can make something happen. I barely referenced this struggle in an instagram post a few months back and a dear friend reached out to tell me her infertility story. It’s a story I might never have heard if I hadn’t opened myself up to that possibility, and I’m so grateful for it.
  • I must be a failure because I can’t seem to make this goal happen - I don’t want people to think that. You can never fully control what people think about you - all you can do is live on your own terms. Sharing this story - especially before it’s a “success” story has become really important to me. I know that at least one person will read this and it will make them feel less crazy, lost and alone. And that’s more worth it.
  • And there is no “happy ending” yet to share that would make the struggle story triumphant. This is perhaps the biggest reason I felt this was important. It’s our nature to tell stories, especially our own, with a beginning, middle, and end. Nearly every story I read about people struggling (in particular with infertility) is only shared after there is happy news that puts a button on everything. But what about stories in progress? The ones without the ending and the button? The struggles that go on with no end in sight? There aren’t enough of those stories - it was time to add mine because I know it will help someone else who hasn’t made it through to the happy news just yet.


Recognize there’s more to the story with everyone you follow and everyone who inspires you.

With my “Branding with Annie” workshops, my newsletters, speaking and other things I do, I realize that sometimes it may be easy for others to perceive me and the business I’ve created to be “perfect” and therefore, personally unattainable.

But my business goes through seasons of success and struggle, like any business.

And I, as a business owner, also go through seasons.

Have you noticed that life tends to happen in spheres? When one sphere, like say your business is thriving, that’s when your home life is a mess or your friendships are in chaos? Nothing ever seems to all be happy/stable all of the time.

But that’s the journey we’re on. We solve problems because life is conflict and adventure.

I would not be real with you if I acted like all of this happens overnight and without conflict and challenge. As the saying goes, it does take ten years to become an overnight success.

So if you’ve ever thought of me as an example or reason why you can’t succeed - that my success is unattainable - I’m here to tell you that there’s more to the story.

In my personal life, I’m in the middle of a story and I don’t know how it will end when it comes to my journey of having family. And what is more valuable to you as a part of my community - to act as though this is easy or to share that nothing worthwhile is ever easy?

Whether this article was for you or not, I appreciate you reading. Whether it’s your business that is struggling, or your personal life, or something you may never feel comfortable sharing in a public way - just know that it doesn’t need to hold you back from the life you want. Success is not unattainable for you. What you’re going through is your turn in a particular sphere, they are worries for the worry tree that we all have our own leaves on.

I think the more that people who lead and succeed in business can share the people and the real life behind what they do - the better. People invest in people in the end, so I hope I’ve helped to you to leave room for that possibility for yourself and I will too.


And if any of this really spoke to you, I think you'd enjoy these other stories I've written around this subject:


Next week, “Being Human in Business” continues

I’ll be back soon with next week’s article that’s a bit of a twist and continuation on this front.

Is there anything you struggle with sharing openly as a small business owner? Let me know - I’d love to encourage and support you.


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