If you take a peek at my resumé, you’ll see a story of persistence and success. For the most part, my tenure at organizations is impressive. With rare exception, I’ve been successful – and promoted. Yes, there was that one time when I only stayed at a major airline for a year; a perfect opportunity at a global entertainment retailer was the reason I took the leap from one industry to another in short order. At the global retailer, I was provided great room for growth, and it was a move to a different city that caused me to finally turn in my resignation.

There’s something you won’t see on the resumé, however, that might be even more valuable than all the accomplishments listed. Yes, this is a moment of complete honesty – honesty that comes with an important lesson for you.

What you don’t see on the resumé is the pool of false starts.

Now, what is a false start? It is the “Oh, that is something I definitely want to do!” jump into a new job or side hustle or dream that is followed by the hard landing of reality.

I remember standing on the edge of the pool at the Hacienda Hotel in Irving, Texas, when I was eight. It was another “business trip for my dad/hotel stay for my mom and me” trip (he called them “vacations” to take the edge off). My mom didn’t swim, and I didn’t either. But the water beckoned, and I was tired of splashing in the shallow end. So, I did what any buck-toothed skinny blonde kid would do.

I stepped on the diving board. And I jumped.

The water was wonderful and cool. And deep. Very deep. I thrashed and splashed and somehow made it to the edge, asking myself why I jumped in the first place. Because I couldn’t swim well, I felt like a failure as I choked down more than my fair share of water. I sat on the side of the pool, my limp legs floating in the cool water. And I cried like a baby.

No, it’s not about the bold leap of starting. It’s about the reality of continuing. 

I’ve never been afraid to start things. But I’ve learned to be better at asking myself the “what will it take?” questions so I don’t drown in the pool of false starts.

On my resumé, you won’t see the custom catering business my friends and I decided to create. We all loved to cook and entertain, and we all had great skill. We created a killer logo,  took some great photos, and jumped – straight into a pot of hot water. We all had talent, but only one of us truly had the stamina to do everything required to make us law-abiding caterers. She’s now on staff at Disney, first as a chef and now as a supervisor who makes sure everything you enjoy while vacationing with Mickey Mouse is excellent.

That’s right. I will prepare a great meal for you should you come to my home. But I am not that person.

You’ll also not see the hard facts of the consulting business a friend and I launched. We’re both highly qualified marketers, so it made sense to offer our expertise to small businesses and organizations needing help with branding. I still love offering that expertise, and manage marketing for a nonprofit while consulting on a freelance basis. My friend is now using her expertise to hone user experience for a global IT giant. As for the consulting business, it languished because neither of us was ready to focus our energy purely on cold-call selling.

There’s also the cookbook I planned to write, the travel blog I thought would be cool, and the “create a date” business I just knew would be perfect for guys who needed a perfect experience to impress and woo someone. And did I mention the bed & breakfast? That one didn’t get past the doodles on paper.

Yes, I’ve never shied away from big ideas.

It’s not about the starting. It’s about the enduring, the keeping on, the punching fear in the face when it says, “your plan is worthless.”

It’s about rising again after a stumble. It’s about the long walk when refreshment is nowhere in sight.

On that hot summer day at the Hacienda Hotel, I cried like a baby because I couldn’t swim well. But that bucktoothed blonde girl asked some important questions, took some calculated risks, and kept walking over to that diving board so she could try again and again.

That bucktoothed kid has something to tell all of us – the 25-year old me who was ready to take on the world, the 40-year old me who was ready to create her own world, and present-day me who is tempted still to take leap after leap. She wants you to remember these words too.

The kid says, “Don’t ask yourself, ‘Is this something I want to do?’

Instead, ask yourself, ‘Is this something I want to keep doing?’”

That’s right.

Now, you and I don’t need to become people who are completely averse to risk. My resumé is filled with the same prayer-covered, calculated risk as the hotel diving board. I’ve changed industries, modified my career path, and even downsized so I could have the flexibility to try my hand at new things – like writing books. There are still fears to be confronted, days when I wonder if I’m truly contributing anything of real worth. I may still face a false start down the road. But overwhelmingly, the drive and passion remain to “keep doing.”

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Here are three important questions to keep you from drowning in a pool of false starts.


Check your motivation, that internal “what’s in this for me?” Be honest with yourself.

Ask: “Why do I want to take this risk? What do I stand to gain from saying “yes?” Do I really want to commit to doing this endeavor – even after the excitement and attention fade? Would I still want to do this if I received no notoriety from it?”


Check your capability. Again, be honest with yourself.

Ask: “What do I actually KNOW about the risk I want to take? What do I still need to LEARN about it? How wide is the gap between what I know and when I can start – and am I ready to stand in that gap and do what it takes to learn?”


That’s right. Check your true willingness.

Ask: “Am I ready to invest my time, talent, and resources to make this risk a reality? Am I ready for the impact of success – or of failure? Am I ready to ask for help? Am I ready to keep doing?”

That bucktoothed blonde girl quickly summed up all three of these questions as she stared at the shallow end of a hotel pool and decided it was time to swim. She knew it was beneficial to swim no matter what her mom thought, she knew she had a lot to learn, and she was ready to use those hands to move her forward.

Now it’s your turn. Ask the questions – and take the leap.