Self-Coaching 101: Four Questions for Better Decisions

This article will help you make friends with your own perfect timing for making big moves rather than blindly chasing the ever-seductive idea of “more.” It will help you listen to your true self.

At the very least, it will share how I found my own wise response to an all-too-common story in the world of business ownership:

The pressure of bigger, better, shinier, faster.

Here’s how it begins:

Years ago, when I was still a touring musician, I saw Marianne Williamson speak. She shared a story about her early success.  

When her first book hit the bestseller list, she felt pressure to “play the part” of the best-selling author. This meant – among other things – moving to a bigger home. She described the chaos and stress this created, concluding with her lesson (which I’m liberally paraphrasing):

When you become successful, there are so many moving parts and so much you’re getting used to. Adding more change will add more complexity (and more expense) to your recently more complicated life. Think twice when you are about to jettison yourself into new external trappings.

The Business Siren Song: If Some is Good, More is Better

At the time, I gave this no thought. 

After all, I wasn’t planning on turning into Beyonce anytime soon. I had zero pressure to move into a bigger anything.

But years later, when I started a company, it did get successful. My accountants and lawyers raised their eyebrows and offered me to sit awhile. I found myself in circles with people who were running eight-figure businesses, some of whom had several homes, private jets, and other assorted goodies. Also, some of my close colleagues were now spending millions on their homes, posting photos on Instagram, and entertaining clients lavishly and publicly.

Enter the pressure. It wasn’t blatant pressure. No one was telling me to do it. It was just one of those “This is what you’re supposed to do, right?” kind of things. Time to get a big shiny house and play the part of the successful entrepreneur! In a culture that trains you to consume from the day you’re old enough to say “Mine” – it’s often easier to just do what’s expected of you: Get more stuff. After all, “If some is good, more is better.”

If you can get an A, work a bit harder to get an A+.

If you’re going to Gentle Yoga, why not go to “Hot and Painful Yoga” instead?

If you have some house, then more house will make you happier.

And this is where Marianne Williamson helped me press pause. Not because her story gave me an instant answer. Instead, it called me to ask myself some deep questions and examine this pressure more soulfully.

Enter Self-Awareness: The Key to Your Success

Getting methodically clear about everything from your current circumstances to your needy ego will help you extricate yourself from the blind external pressures for more. It will help you make choices that are authentic to your soul.

In other words, there is no recipe. You have to be willing to pause and listen to yourself.

Here are the four questions I used and continue to use as my success expands even today. Consider them, and step back before reaching out to grab the next big shiny anything (house or otherwise)…

1 – Am I honoring my personal circumstances? 

When my business first took off, I had – up til that time – spent 15 years as a musician. The year I broke the $100K mark as a songwriter was a big honkin’ deal. So, yes, I had been successful, but I wasn’t exactly sleeping on mattresses of cash.

And just because I was now the owner of a 7-figure business didn’t make me Warren Buffett. It just meant that I’m good at this thing I do.  

I was fifteen years behind many of my peers in terms of making an exemplary annual income. There’s no shame in this. After all, I got to play music professionally for 15 years. I’ll take that trade-off. But it meant that my IRA had about 26 cents in it. So I had some catching up to do.

Also, my husband has his own business. This puts both of us in the “unpredictable” category. (Though, these days, I think we’re all in the “unpredictable” category. But that’s a whole other blog post.)

2 – Am I honoring who I am?

I teach my entrepreneurial clients several tools for self-understanding – from the Enneagram to the Kolbe A Index to Strengthsfinders. This level of self-awareness helps them build better teams, understand their clients, and most importantly, understand themselves.

So for instance, on the Kolbe A Index, in the “Fact Finder” category, I’m a 2 out of 10. Which means that “A long time ago in a galaxy far far away” is an entire semester of history for me.

Yes, I’m great at coaching and getting to the core of a challenge quickly and intuitively – but I’m not your girl for due diligence on home purchases, let alone all the taxes, inspections and fees. (You know…details.) I honor this about myself and make sure there are people on my team who excel at this tedious work.

Bottom line: For me, big purchases require extra support. I had to weigh whether or not the added stress was worth my time and attention with an already full schedule.

3 – Is this love or fear?

Self-awareness means you’ll encounter your ego. More often than not, when I’m pushing myself into something that doesn’t feel right, I uncover a broken part of me that is 100% preoccupied with what other people think of me.  Oh happy day, there she is again.  When I discover that she’s behind the curtain running the show, it’s up to me to then navigate this tender territory and gently steer in a better direction.

Your broken self – the thing we call “ego” – will try to convince you of all the things you must have, the people who will leave you behind and judge you if you don’t get those things, and all kinds of other unpleasantries. At the end of the day, however, ego is best left out of your decision-making process.

Here’s the best question for cutting to the chase: Am I making this decision out of fear or out of love? Almost always, you will hear the answer immediately.

4 – What Matters Most to Me? 

Do you know – really know – what truly matters to you? This isn’t a question that can be ticked off quickly – like your daily task list. This is one of those things you explore. Which is what I had to do.

What matters most to me is having free time and plenty of space to create. I never want money to be the sole basis of a decision. I never want to have to keep a toxic client because my business needs money. 

Next, I value learning and coaching—more than any goodies you can throw my way. So that’s where I invest my resources – both money and time. 

Authenticity, Not Minimalism

In the end, I didn’t buy a ginormous, million-dollar home. Instead, I chose to stay in my tiny house that I love. I’ve remodeled, landscaped and redesigned it along the way.

Every now and then, someone will remark that I am “Zen” or “minimalist” when they see how I live my life. If I am either of those things, it’s not because I’m naturally wired that way. I’ve created this lifestyle because I’ve confronted the many places inside of me that are decidedly not Zen.

And I’m not minimalist. (Just ask anyone who has checked my luggage at the airport.) My choice to stay in my not-so-big house is not a minimalist choice. It is simply an authentic one. Which, ideally, will be every choice you make in your business as you grow. 

Decisions are the hardest part of what we do as entrepreneurs. So tell me in the comments: How do you ensure that you stay true to your soul while building your business?