5/30 3 Exercises to “Find Your Why” in Business

This morning, a woman leader admitted to me, “I need to connect to my bigger ‘why.’ The summer slump is underway. Companies are cutting budgets.  She was experiencing anxiety about the lack of deal flow coming her way.

I’ve heard this sentiment expressed a few times in the last few weeks. Women wanting to connect to their raison d’ê·tre –the reason they have a business, the reason they do what they do.

Here are three exercises I do with my VIP Day clients to help uncover their why.


EXERCISE 1: The ‘Time Log’ Exercise

Often our ‘why’ lies in a pain point from childhood.

A story:

I left home at 18. Paid for college. Paid for grad school, Paid for every move around the country to come to New York City and do what I wanted to do since I was 4 years old: become a news anchor.

My parents are immigrants and didn’t have the emotional or financial muscle to support my dream.

I got my wish. My agent placed me as a business news reporter at CNN early in my career. Suddenly,  I was thrust into a high profile world,  interviewing CEOs on the floor of the New York Stock Exchange. Where was the playbook for a small town girl to hold court with this level of executive?  I couldn’t find it. I learned by observing others and implementing fast. 

Years later, with my own business, I hired coaches. Truth is—-I needed a coach back then, telling me what I should and shouldn’t be doing. I’ve formalized it by creating the various offerings at the Womens Leadership Lab.

Today, my ‘why’ is that I want to be the champion I wish I had years ago.

When I work with clients, I share “The Time Log Exercise” which asks her to outline her life in 3 year increments, list the major events in each bucket, and theme it.  This deep exploration often uncovers the ‘why.’  I learned this exercise from Elizabeth Cross, who hosted a workshop for my Women’s Leadership Lab.

For example, one of my clients had spent a lifetime working in fintech before it was called ‘fintech,’ getting ‘unbanked’ women in 3rd world countries access to bank accounts. Now she was investing in female founders in the climate tech space. But she couldn’t connect the dots.

When we did the ‘time log exercise,’ we uncovered the connecting dot. There was a time when she had given her all to a project. She was about to deliver her first child —and was fired. That experience was a seminal moment in her career: It deeply impacted what it meant for her to be woman, a new mother, and a leader. Today, she is actively changing the narrative around mother hood and business. Just because a woman elects to have a child, doesn’t mean it’s a ‘career end.’ She jumps in as fractional COO to keep the business running or invests in a startup where a new mother and business owner hires bandwidth to keep the business running.


Exercise 2: The ‘Core Values’ Exercise

In the last year, my biggest accomplishment has been establishing my tagline: Adventure Leadership. 

I was dropping my clothes off at Rent the Runway one morning and dropped into conversation with the attendant about my upcoming retreat to Marrakech. The woman called others over to hear me speak.  I was at a restaurant on the Upper East Side, talking about my annual sail.  A man just behind us leaned over and said, “How can I get on your trips? That sounds fantastic!”

I had always hosted inventive and creative retreats for my women’s leadership platform. I just wasn’t actively talking about it.

Arriving at this ‘why’ was a two parter:

Again, my pain point lay in my childhood. As the product of an immigrant household, I wasn’t allowed to do much as a kid. No Friday night football games. No birthday sleep-overs. No choir practice. I once agreed to go a weekend leadership retreat. The friends showed in my drive way. My parents stood to the door and said, “She’s not coming.”

Fear informed so much of their existence. That went up 10-fold because I was a girl. So today, as an adult, the pendulum has swung completely in the opposite direction.

I want to try everything.

Do everything.

Feel the fear and plow through it.

Want to know what my top core values are? Adventure, Beauty, Freedom.

No surprise there.

This is the first exercise I traditionally do with clients. You can do it too. 

Look at the list of 50 core values on this list. https://jamesclear.com/core-values

Pick 10.

Pick 5.

Narrow it down to the top 2. Ideally these are the two that are important to you when you strip away work.

In this podcast interview with me, Lisa Druxman, CEO of Fit4Mom, talks about building a life and a business around her core values.  Listen here.


Exercise 3: Find Your ‘Ikigai’

The Japanese have a philosophy called “Ikigai” which literally translated means “A reason for being.”

That ‘why’ sits at the intersection of four important questions, listed here.


My other ‘whys’

I have two other ‘why’s to conclude this article.


My Commitment to Exercise:

I get up at 5:30am and workout first thing in the morning 5-6 days a week. Why? Because I’ve never loved my body. It affected my self esteem.

In order to change that, I now get to bed by 9:30pm, and make the first 90 minutes of my day about my own self care. My bigger’ why’ is what gets me out of bed when the alarm goes off. The payoff stares me in the face every time I look in the mirror.

I like what I see now.


Not drinking:

I used to drink scotch like a champ. Recently I gave it up. Coach Gabrielle would talk to me about “getting downloads from Source.”

I would sit still for 20 minutes each day in meditation. I wasn’t getting sh**. I was at an event, celebrating non alcoholic beverages (there are so many now) and I heard an influencer say, cutting out alcohol made the line clear. She had so much more access to ideas and creativity. In other words, a clear download from “Source.” That was the ‘why’ I needed. I want to build a 7 figure business. In order to do that, I need complete access to my complete brain.

I do have 2 glasses of wine a week. But— I remember my bigger ‘why’ —access to big 7 figure ideas— when I say ‘no’ to the third.

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