Explore the authentic journey of entrepreneurship with insights from a career coach. Discover the challenges, rewards, and honest conversations that fuel business growth.
Here be dragons. That phrase was once used to mark the unknown. Uncharted waters. Unfamiliar territory. Places people had not fully explored yet. It was not always a warning to stay away. Sometimes it...
Building a Life You Choose / Career Transition / Entrepreneurship / Exploring the Unknown / Franchise / Starting a Business
by Sean · Published May 8, 2026
Most people have no idea how franchising actually works. They think they do. They see a fast-food restaurant, a hotel, or a fitness center with a familiar logo and assume the giant corporation owns...
Exploring the Unknown / Life Transitions / Mindset & Motivation / Personal Growth / Self-Development
by Sean · Published April 16, 2026
Why staying busy feels productive… and still leaves you in the same place There’s a point in almost every meaningful pursuit where things stop making sense. Not because you’re failing. Because you’re doing everything...
Career Transition / Entrepreneurship / Exploring the Unknown / Life Transitions / Redefining Success / Uncategorized
by Sean · Published March 29, 2026
There’s a moment sailors don’t talk about much. Not the storm.Not the triumph.Not the arrival. The moment they talk about quietly, if at all, is the day the shoreline disappears. You look back… and...
Building a Life You Choose / Entrepreneurship / Exit Strategy / Exploring the Unknown / Franchise / Starting a Business
by Sean · Published March 26, 2026
When Spanish explorers set sail for the New World, they weren’t just chasing discovery. They were chasing something they could bring back. Gold, trade routes, land, opportunity. Whatever the objective, the mission wasn’t complete...
Building a Life You Choose / Career Transition / Entrepreneurship / Exploring the Unknown / Life Transitions / Personal Growth
by Sean · Published March 19, 2026
Leaving familiar ground is often treated as the main event. The big decision. The bold move. The moment that separates people who “go for it” from those who stay put. That framing misses where...
Career Transition / Entrepreneurship / Exploring the Unknown / Taxes
by Sean · Published March 18, 2026
A quick note before we start: I am not a lawyer, accountant, or tax advisor. This article explains general concepts about business taxation. It helps people exploring entrepreneurship better understand how the system works....
Building a Life You Choose / Entrepreneurship / Exploring the Unknown / Preparation / Starting a Business / Taxes
by Sean · Published March 16, 2026
Before We Set Sail Before we dive into the waters of business taxes, a quick note. I am not a lawyer, accountant, or tax advisor. The information in this article is meant to explain...
Building a Life You Choose / Career Transition / Life Transitions / Purpose-Driven Work
by Sean · Published March 5, 2026
My wife posted this picture on Facebook the other day to celebrate our 31st wedding anniversary. When I looked at it, I saw two kids who had just gotten married. And it made me...
Entrepreneurship / Exploring the Unknown / Starting a Business / Taxes
by Sean · Published January 29, 2026
Business ownership opens doors most people never see, including how taxes actually work. This article examines common tax concepts that business owners navigate. This is not advice but territory worth understanding before the journey...
Building a Life You Choose / Exploring the Unknown / Life Transitions / Mindset & Motivation / Personal Growth / Self-Development / Uncategorized
by Sean · Published January 13, 2026
Here Be Dragons usually leans into metaphors. Maps. Warnings scribbled in the margins. The places where certainty runs out, and judgment has to take over. This post is a little different. I’m not abandoning...
Entrepreneurship / Exploring the Unknown / Preparation / Starting a Business
by Sean · Published January 6, 2026
Morning on the Nile didn’t begin with fanfare. It began quietly. A bit of river breeze. The shuffle of sandals on packed earth. A loaf of heavy bread. A cup of thick, familiar beer....
America wasn’t built by corporations. It was built by people who owned things. Shops. Trades. Farms. Small operations where work and ownership lived under the same roof. If you wanted stability, you didn’t apply...
A Here Be Dragons exploration of job security, risk, and the quiet work of building your own path There are moments when the ground shifts under the entire working world. Sometimes it’s a recession....
Building a Life You Choose / Career Transition / Entrepreneurship / Exploring the Unknown / Starting a Business
by Sean · Published November 25, 2025
The conversation about business structures can feel unfamiliar. It’s a bit like sailing off the edge of the known world. One moment you’re excited about starting a business, and the next you’re lost in...
Career Transition / Entrepreneurship / Franchise / Life Transitions / Veterans
by Sean · Published November 18, 2025
I started to think more about my clients after Veterans’ Day this year. Some have left military service, and others are considering it in the future. They all had a lot in common. Leaving...
Entrepreneurship / Exploring the Unknown / Mindset & Motivation / Personal Growth
by Sean · Published November 14, 2025
Lessons from Scouting that apply to business — preparation, resilience, and teamwork. Introduction: Following the Trail Into the Unknown The first High Adventure trek I led as an adult was a 60-mile paddle trip....
Starting a business is exciting. It can also be terrifying, especially when you get to the part where you have to answer the big question: How do I pay for all this? Most people...
Building a Life You Choose / Entrepreneurship / Exploring the Unknown / Franchise / Starting a Business
by Sean · Published November 7, 2025
The Myth of the “Self-Made” Entrepreneur Most people imagine an origin story when they think about starting a business. They picture the lone visionary. They envision the napkin sketch and the sleepless nights in...
Building a Life You Choose / Entrepreneurship / Purpose-Driven Work / Redefining Success / Risk Tolerance
by Sean · Published November 5, 2025 · Last modified November 10, 2025
Exploring meaning, autonomy, and time freedom in entrepreneurship The Surface Story: Money Let’s be honest, money is often the spark that ignites interest in business ownership. You want financial freedom, stability, or the ability...
Career Transition / Exploring the Unknown / Life Transitions / Mindset & Motivation / Personal Growth / Risk Tolerance / Self-Development / Starting a Business
by Sean · Published November 4, 2025 · Last modified November 5, 2025
The Early Emotional and Mental Realities of Business Ownership The Myth of “Ready” When people say they’re waiting until they’re “ready” to start a business, they usually mean they want to feel safe. They...
Entrepreneurship / Exploring the Unknown
by Sean · Published November 4, 2025 · Last modified November 5, 2025
Back when maps were hand-drawn, cartographers would mark the edges of the known world with three simple words: Here be dragons. It was their way of saying, “We don’t know what’s beyond this point,...
