Hey Reader,
I’ve got three things for you this week—each one meant to help you navigate the important work you’re doing in the world:
A Powerful Conversation on Success, Identity & Marriage
This week on Good Work, I sat down with the brilliant design educator Matt D. Smith (@mds). We talked about what happens when outward success outpaces inner clarity—and how to find your way back.
We cover:
- The three inflection points that shaped his career
- How his marriage became the foundation of his work
- Why validation will never be enough—and what is
Little Leadership Lesson: What to Do When You Have Too Many Good Ideas
Ever feel overwhelmed by options? In this week’s short lesson, I share 3 powerful questions to help you cut through indecision and choose your next move with confidence. It’s based on a real coaching moment from this week.
(That’s coming right after the photo—keep reading.)
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OK, let’s get to it:
A Beautiful Photograph of the Natural World
It’s a season of possibility and hope as Spring brings blossoms to the trees in my yard and city. I’m fascinated by the ways in which the seasonal cycle influences our own energy, ability, and willingness to grow.
Little Leadership Lesson: What to Do with Too Many Good Ideas
More is lost by indecision than wrong decision. Indecision is the thief of opportunity. It will steal you blind.
— Marcus Tullius Cicero
A quick editor’s note that I’m skeptical of this quote’s original attribution. I don’t see any indications that this is directly translated from Cicero’s works. Nonetheless, it is popularly attributed to him and makes an important point about leading well.
My Take: Three Questions to Get Decisive in the Face of Multiple Paths Forward
One of my clients (thank you!) in group coaching this week shared multiple business ideas that could help them make a breakthrough to a new level of both revenue and personal growth.
The problem: there’s a strong argument to be made for any one of the ideas. And in the face of multiple good ideas, I see far too many highly talented and intelligent people choose… nothing.
This seems like a safe choice. With time, we might learn more. We might find the key to making the right choice. But not choosing is in fact a choice. It is a choice to remain still, not because it is the best choice, but because it prevents us from facing the choice at all.
Here are the three questions I asked to help this entrepreneur (who is an expert in their field AND has been in business for over a decade):
- If you force rank the ideas by excitement, what order would they end up in? The one rule here is you must quiet your mind, turn off your logic, and listen to your body. If you imagine a string between your heart (or your gut or your soul) and each idea, which string is tugging the hardest?
- Start from your revenue goal (let’s say you want to add $100,000 in revenue). What would have to be true for each idea to hit that revenue goal?
- Given your answer to #2, do the backwards math to understand how many potential customers you need to reach in order to meet the revenue goal. Which ideas do you still have confidence in, given the mechanics?
Here’s what I’ve learned from my own experience—and from hundreds of hours coaching world-class entrepreneurs:
- If you’re not excited about an idea, you won’t follow through. Even if it could make great money. The only exception? If someone else on your team is excited and owns execution.
- Clarity on the mechanics beats vague goals. Saying “I want to earn $100,000” is fuzzy. Saying “I need to sell 40 units of a $2,500 program to a premium audience” is actionable.
- Once you know the math, it’s just a question of reach. 40 sales → 80 serious conversations → 800 qualified leads (for example). So the real question becomes: Can I reach 800 potential buyers for this idea?
These kinds of questions tap into both intuition and logic to help avoid indecision. At this point, it’s always a possibility to say “I like where I am better than I like the idea of doing the work to bring any of these ideas to life. I choose nothing because it’s the decision that reflects what I value most.“
Nothing is more powerful than a committed and thoughtful “do nothing.” It’s the passive ones that slowly drain our potential and leave us hiding out of fear and anxiety.
The Lies We Tell Ourselves About Success with Matt D. Smith
What if everything looked successful on the outside—but no longer felt right on the inside?
This week on Good Work, I’m joined by Matt D. Smith—world-class designer, founder of Shift Nudge, and the creative force behind some of the internet’s most iconic visuals. But this conversation isn’t about pixels or process. It’s about the real work: identity, marriage, purpose, and redefining what success even means.
We talk about:
- The 3 pivotal moments that changed Matt’s path
- How his marriage became the foundation of his creative career
- What it took to let go of external validation and find internal peace
It’s a raw, thoughtful conversation about building a life and business that actually feel good—rather than just looking impressive.
Group Coaching: The Best Way to Get Support During a Major Period of Transition, Transformation, or Growth in Your Business
Two things I’ve observed to be true:
- The more successful you become, the more isolated you’re likely to be
- The more successful you become, the *more* support you need
Success is isolating because the more you grow, the less the people around you can relate to your experience of life (and the more they assume you have it all figured out). It becomes harder to find peers in a similar situation. There are fewer mentors or teachers that have been where you want to go.
This progressively leads to a realization: there is no roadmap from here. There is only your judgment, your intuition, and your strategic thinking.
But this doesn’t mean you have to go it alone. And if you try, it will likely lead to unnecessary mistakes, loneliness, and a sense that you’re grinding it out… for what?
We’re made to live, play, and work in community with other humans. We’re social animals who need encouragement, belonging, and to form our best thinking through relationships.
Group coaching solves for both of these needs. You don’t have to do it alone. And you deserve support along the way. I’ll be the curator of the experience, but the group’s wisdom is what will help you continue to realize your vision for your business.
I have cohorts starting every few months, so it’s never NOT a good time to apply.
Find Me on Socials
I just hired a fantastic contractor to help me be much more present on social media — specifically LinkedIn and Instagram. Like many people, I have the problem that there’s only one me and there are many demands on my time.
Even though I create a ton of content and have much more I could be sharing, I rarely have the time to publish on social media… until now.
I’ll be on Instagram and LinkedIn much more frequently starting in April. It’ll all be my own work and words and I’ll really show up to chat in the comments.
So if you don’t already follow me on Instagram and LinkedIn. Excited to deepen our connection there!
Thanks for Being Here!
Listen, I worked in email software for years. I know that an email with five calls to action is a dumb thing to do. So thanks for reading all the way to the end and thanks for being able to process multiple things at once.
I know my email cadence and personalization are less than ideal — that’s because I give my best capacity to 1) my family and 2) my clients, which has left me with far too little time for consistency in my content.
I’m already working on hiring the support *I need* to fix that. Thanks for hanging in there in the meantime! I hope the emails I do send bring you a little bit of joy and a lot of value.
