Why the 'Risky' Path Might Be Your Safest Bet
The genius paradox of taking risks.
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Don’t you think that’s a bit ‘risky?’ Is that really a job though? What if you never succeed?
We have a peculiar relationship with success in our society. When we start out, the fears of others are pressed upon us warning us of the dangers that it may never work out.
When we succeed at something, we’re still slightly antagonized as to whether or not we’ll be able to do it again… or even better our best.
Ironic, right?
When first told people she wanted to be a writer, they responded with fear: "Aren't you afraid you'll never succeed?"
Years later, after writing the international bestseller "Eat, Pray, Love," people approached her with a different fear: "Aren't you afraid you'll never top this?"
This paradox isn't unique to writers like Gilbert… nor artists, nor entrepreneurs, nor anyone else following their calling because they simply need to.
I’ve met a former accountant who was criticized for leaving his $250,000/year job to create a fulfilling life as a farmer who now grosses $10M annually.
I’ve encountered engineers who felt stifled by corporate overlords for not allowing their “artistic” side to flourish, which would have also created strategic solutions for their company… Two of them later became product designers online making 10 times more money and loving what they do.
Here’s the thing… it’s not about the money, but isn’t it ironic that while traditional paths promise certainty and safety, it's often the non-traditional routes—pursued not for money, but for creative fulfillment—that lead to both spiritual and financial prosperity.
Isn’t it also ironic that there seems to be a bit more ‘safety’ in trusting your soul?
The genius paradox of taking ‘risky’ paths is that it may be your safest bet.
This begs the questions — what if our entire framework for thinking about success is backwards?
What if the "safe" path isn't as secure as we think, and the "risky" path isn't as dangerous?
The answer lies in a revolutionary approach to creativity and success that successful creators and entrepreneurs have been quietly using for years.
Redefining Success & Genius
The Renaissance brought us many gifts… In her now famous TedTalk, Elizabeth Gilbert points out that it also saddled us with a burdensome idea — that genius comes from within…
that we alone are responsible for our creative and professional success. This notion has crushed countless spirits under its weight.
Before this shift, ancient Romans believed that genius wasn't something you were, but something that visited you — a divine spirit that assisted in your work.
They understood what many of us have forgotten: that our greatest achievements often come through us, not from us.
When we embrace the idea that our role is to steward our gifts rather than generate them, we free ourselves to take bolder actions.
When we stop viewing success as a purely internal responsibility and start seeing it as a collaboration with our God-given opportunities, divine timing, and the gifts we've been blessed with, something profound shifts.
Instead of trying to manufacture success through sheer willpower, we can focus on being faithful with what we've been given, showing up consistently, and remaining open to divine inspiration.
I can personally attest to this…
I didn’t go to school for writing.
I was consistently asked by my teachers and professors to redo my papers in school because my ideas were not quite developed… I was in agony over constantly redoing them.
I was consistently asked to write emails for people I worked with, classmates and other colleagues.
My clients asked me to write the “copy” for their websites, marketing campaigns, social media, packaging and everywhere else their brand existed.
Countless contracts, business plans, theoretical papers, you name it… I was asked.
The irony I always thought… I’m not a writer (publicly). Privately, I’ve been one for 30 years, but I couldn’t own the title.
However, to everyone else, I was.
They saw how I developed my ideas and communicated them.
What I ultimately learned is that God was leading my hand through one of His gifts he bestowed upon me.
Often others will see the gifts in us before we even understand them ourselves.
Yet others will know from a very early age such as Michelangelo.
What has profoundly impacted my life is understanding Gilbert’s reminder that genius doesn’t come from us, but through us.
When I ask God for focus… He points to the pen.
When I ask myself for focus… I distract myself with a different direction.
When I follow the pen, my growth is substantial.
When I follow my distractions, my growth feels stagnant.
Here’s my point…
Every one of us has genius that wants to come through us, but we have to receive first, initiate second.
We have to be willing to listen to our gifts, have faith in their direction and share them with the world… unbiased of what it will return us…
...because the truth is... the greatest risk in this equation is not taking the risk at all.
It's ignoring the gifts that have been placed within us and dismissing the guidance that's trying to work through us.
Think about it - when we follow traditional paths purely for their promised security, we often find ourselves less secure than ever.
But when we trust the gifts we've been given and follow where they lead, even when that path seems uncertain, we discover something remarkable… what looked like the riskier path actually offers deeper security.
Let me show you what I mean...
REFLECTION…
Think about a time when others recognized a gift in you that you hadn't yet seen in yourself. What were they seeing that you weren't?
When in your life have you felt most "in flow" - where work felt like it was coming through you rather than from you? What were you doing in those moments?
The Hidden Safety of “Risky” Paths
The data tells an interesting story…
45% of entrepreneurs started without college degrees
92% of successful creators started as side hustles
88% of high earners changed careers at least once, if not twice
67% of successful creators had no formal training
82% started with less than $5,000
64% successful entrepreneurs failed previous ventures
89% of creators took 2+ years to reach sustainability
38% of millionaires never finished college
71% of successful online businesses run by self-taught owners
93% of high-earning creators learned through practice
These numbers might seem to suggest that the path to success is random or chaotic, but there's a pattern here - one that aligns perfectly with Gilbert's philosophy of creative work…
The traditional path promises certainty but delivers vulnerability to market changes, corporate downsizing and technological disruption.
The non-traditional path, while appearing risky, actually builds in safety through diversity of skills and income streams.
Mark Manson — from business consultant to blogger/author. His decision to leave his conventional career path was met with skepticism, but his book "The Subtle Art of Not Giving a F*ck" became a global bestseller. He now generates income through book royalties, his subscription-based website, speaking engagements, and online courses.
Seth Godin — from a career in software and book packaging to becoming a marketing blogger/author. He’s published 20+ books, runs the altMBA program, speaks globally, and writes one of the most popular blogs in the world. He famously wrote many unsuccessful books before "Purple Cow" became his breakthrough.
— from dropping out of community college and working odd jobs at places like Subway to launching Nasty Gal eBay store ($100M), writing a New York Times Best Seller #GirlBoss and starting Girl Boss Media amassing ventures across publishing, speaking, online education, investments, brand partnerships and more.
Notice a trend… all of them left traditional roles or paths… all of them applied their unique gifts… all of them went on to create significant impact… all of them found safety and security in their path.
What these creators and entrepreneurs have discovered is a practical framework for turning seemingly risky paths into sustainable success.
It's not about waiting for lightning to strike or forcing creativity through sheer will. Instead, it's about developing a systematic approach to catching and channeling inspiration when it arrives.
REFLECTION…
Looking at these success stories, which statistic challenges your current beliefs about "safe" versus "risky" paths? Why does it challenge you?
What unique combination of skills and experiences do you already possess that could become your own "non-traditional" advantage?
What "traditional" beliefs about success are you holding onto that might be limiting your potential?
The Creative Process As a Partnership
The real magic happens when you understand how to partner with creativity instead of trying to control it.
Influential American singer, songwriter, musician, Tom Waits, offers a revolutionary perspective on this partnership. One day, while driving on the Los Angeles freeway, a song came to him.
Instead of feeling the usual panic about potentially losing this creative spark, he did something remarkable - he spoke to it directly — "Excuse me, can you not see that I'm driving? Come back at a more opportune moment."
The specific anecdote Gilbert shared in her TedTalk about Waits marks a pivotal shift in his approach to creativity.
Earlier in his career, he embodied the tortured artist stereotype — struggling with the pressure of creativity and battling anxiety about capturing ideas.
The freeway incident Gilbert describes represented a turning point where he began treating creativity not as something he had to desperately grab and control, but as something he could have a relationship with.
While his work remained just as challenging, the anxiety around it dissolved when he stopped trying to force creativity and started treating it as a collaborative relationship.
And this shift from anxiety to partnership isn't just about creativity — it's a practical framework for building sustainable success.
Consider this for your own journey…
Build a creative partnership —
Create Space for Inspiration — Instead of trying to generate brilliant ideas on demand, set up conditions where inspiration can find you. This might mean:
Keeping tools ready to capture ideas when they come
Setting aside specific times for creative work
Creating an environment that welcomes inspiration
Develop Your Creative Rhythm — Just as Waits learned to have a conversation with his creativity, you can develop your own dialogue through:
Morning reflection and idea generation
Focused execution time when you're at your best
Evening review to integrate what you've learned
Trust the Process — Remember that creativity, like any partnership, develops over time. Start with small, consistent practices:
Establish basic capture systems for your ideas
Build regular creative routines
Allow your process to evolve as you learn what works for you
The Power of Partnership
The beauty of this approach is that it removes the pressure of having to be brilliant on demand. Instead, you're creating a sustainable relationship with your creativity. Some days will bring breakthrough moments; others will be about showing up and doing the work. Both are equally valuable.
As Waits discovered, when you stop trying to control creativity and start partnering with it, something profound shifts. The work becomes less about forcing outcomes and more about being ready when inspiration arrives.
**I’m currently developing an All-in-One Notion Dashboard to help you streamline your creativity, productivity and income — so you can manage the technical, creative and financial aspect of your work easier. it's not just another project management tool or content calendar, but a complete operating system for the modern creative professional who needs to be both artistically fulfilled and commercially successful. You can join the waitlist here.
Creating Sustainable Success Patterns
Success on the non-traditional path requires more than just inspiration — it demands a systematic approach to building your future… we need flexibility and structure… the ability to create fluidly and earn cumulatively.
Here’s how you can use what I call a "Success Stack Framework.”
Skill Inventory Assessment
Revenue Stream Development
Action Steps (Short Term)
Sustainable Steps for Momentum & Longevity
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