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The Most Important Question To Ask Yourself

People often think that the best way to predict the future is by collecting as much data as possible before making a decision. But this is like driving a car looking only at the rearview mirror—because data is only available about the past” - Clayton Christensen “How Will You Measure Your Life”


I love this quote. It immediately makes me think about the year I spent traveling. Over the course of 12 months, my husband and I drove 6,000+ miles through US National Parks, hiked over 400 miles, lived and traveled abroad and visited many, many, many local coffeeshops. We lived life that year only looking at the road ahead, focused on what we wanted to experience. Life was admittedly much less complicated - we didn’t have any kids (we now have two under 5), didn’t have any pets, didn’t have a mortgage and didn’t have to worry about an ever present, totally life altering and currently raging global pandemic.


Still, when I think about that year, I measured my happiness and worth not in how many hours I worked or how much money I made but how I felt, how I connected to those around me and how I experienced living.


I would describe myself as a type-a person generally motivated by achievement and if I’m honest, someone telling me that I’m doing a good job. Captain of this, that and the other, straight A student, quick climber of the corporate ladder, ready to raise my hand for any opportunity, and motivated by measurable results that I felt validated my hard work. Many of the people that I work with today would describe themselves similarly. I recognize these aspects about myself as valuable and I know that they have been important in helping me achieve success as a professional and as a person. I would imagine others who resonate with these qualities feel similarly.


But there’s that word that I want to talk about. Success.


Success. How do we measure it? How does our definition of success support our ability to be happy and fulfilled in this world?


Is it how much money we make? How many deals we close? How many hours we work or how quickly we grow our teams? Is success how others measure your performance at work or if you’re able to buy new house? What you post on social media? If your kids eat vegetables?


As a coach, I ask lots of questions to my clients all the time. But, I think questions have hierarchy. If I were to articulate the “one ring to rule them all” question (hey, Tolkein fans) it’s this:


What does success look like to you?


Let that sink in.


What does success look like to you?


Back to Clayton’s quote, oftentimes we resort to measuring success based on what our experiences have told us is “right”, what we "should" do or how it's always been done. A sales executive measures success in terms of revenue and deals. A CEO measures success on their ability to 2x their business over twelve months. A product manager measures success in terms of a successful product launch.


Yes, these metrics are important. But are they everything? If you were to meet this definition of success, how would you feel? Whole? Or a bit like a donut - all glossy and decorated but missing something in the middle?


As a business owner, I’ve had to get real with myself on this question. I’m a bit of a goal-post mover, which means that if and when I set “rear-view mirror” measures of success, meeting them just means moving on to the next goal post. A new obstacle to overcome, a new goal to hit. That feels okay, until it really doesn't... especially if and when that goal post is not driven by your true wants and desires.


For me, I’ve found that the answer to this question lies in articulating and clarifying my values. Impact, adventure, autonomy, curiosity, authenticity. What does it look like to live these out through my business and my life every day?


Like most things, this is work in progress for me. But I have found that embracing this question, talking through my articulation of success and sharing it with people that I trust has helped to create pockets of fulfillment that weren't there before. It's also helped me to authentically celebrate wins and progress, which can be a real catalyst for reaching that sought after feeling of flow.


So, adjust your view. Look forward and ask yourself - what does success look like to you?

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