5 questions to ask yourself about your ambitions.

What are your ambitions? Are they big? Are they small?

Here’s the one thing I believe, ambitions are like Cinderella’s shoe. There’s one that fits you, and all the others will give you blisters and hurt like heck.

Several of the conversations this week with people exploring the Future Them, have centered around ambitions. I noticed that so many had pre-conceived notions about their own. Many, after further inspection, were not only holding them back but frankly making them miserable. We’ve got enough happening in our lives that being miserable around something that’s just not true is even worse.

What are the questions I ask, and why?

When was the last time you thought about your ambitions?
So often, when I ask this, I hear, “Oh, I’m not very ambitious.” Almost like it’s a character flaw. It’s like the act of being ambitious is so selfish that even contemplation is not allowed—Pish posh folks. Hang out with anyone under the age of ten, and you’ll see brilliant ambitions running wild. Do we think these ten-year-olds are being selfish, or are we excited for their future? Considering your aspirations, I believe, is being an agentic optimist. The future can be bright because I can make it so. 

Do you believe your ambition has to be big to be worthwhile?
We live in a world where we celebrate the “never been done before” and the “fastest, biggest, tallest.” With the introduction of social media, this accolade has shifted from the few to everyone. While we all know we’re not supposed to value ourselves based on how many “likes” or followers we have on a post? This curated window into each other’s lives exacerbates the concept of comparative culture. Comparisons = I have to be more significant to be worthwhile. Fiddlesticks. Your version of “worthwhile” is yours, and it’s the one that will make you happy.

Do other people’s opinions about your ambition matter?
I think I already answered that one in my comment above. But let’s unpack this idea of other’s opinions a little more. Who do you know who’s manifested an ambition or is in the process of doing so? Do you think they’re doing it, or their success in creating it because someone else’s opinions drive them? When I consider the people I admire, it’s the people who are clearly doing it for their own reasons that inspire me.
Here’s the more challenging question, are you letting someone else’s opinion of you stop you from creating the life you want?

Does it matter if you fail? Will it matter more if you don’t try?
We’ve all heard the expression, “it’s the journey, not the destination.” I’ve also noticed that exploring my own ambitions often manifest, just not quite the way I anticipated. I’d be lying if I didn’t share that my fear of failing, more importantly, failing publicly, often holds me back. It stops me from starting something because I’m not 100% sure it will be perfect and successful. I’m also only too aware that when I at least try, exciting things happen.  My favorite tool to combat this is to ask myself if I’d be angry with myself if I never tried. I then ask, is the consequence of failure all that bad? For me, the answers are frequently “yes” and “no”.

As a leader, are you talking about ambitions with your team?
As someone who’s spoken to over twenty people about ambitions in the last two weeks, I can tell you that a conversation about ambition is the most powerful conversation you can have with another person. No, these aren’t conversations about title and promotion – those are just labels – we’re talking about deep conversations about motivation and authenticity. We’re talking about possibility and potential, and we’re sharing fears and excitement. Here’s the not surprising result. These individuals are motivated and engaged; while curious and probably a bit nervous about their futures, they’re taking ownership of their role and the impact it can have. There’s a bonus benefit to these conversations. A single executive gifted the majority of these sessions with me. At the end of each call, the individual has spoken about how seen and empowered they feel. How grateful they are to their leadership team for this time.
In this working world, people choose to work FOR you, WITH you, or not at all. I  guarantee a conversation about ambition creates “WITH” energy all day.

I’ve leave you with this. I surround myself with ambitious people. You know what’s brilliant about them? They’re often highly ambitious for me. I’m also ambitious for them. It’s like we’re throwing the magic of possibility on each other, which is critically important when things get hard. And when you’re trying to manifest an ambition, things will get hard.

I have all sorts of ambitions. One includes backup dancers. What’s yours?



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