Why Your Side Gig Might Not Be Ready | Over the Bull®
Starting a business is one of the most exciting decisions a person can make—and one of the most dangerous. Over the past year and a half, I’ve watched countless people launch new ventures, chase side gigs full time, or dream…
Starting a business is one of the most exciting decisions a person can make—and one of the most dangerous. Over the past year and a half, I’ve watched countless people launch new ventures, chase side gigs full time, or dream of leaving their jobs to go out on their own. Some succeed, but many stumble. Others are walking blindly into mistakes that could have been avoided with a dose of reality.
This isn’t meant to discourage ambition. On the contrary, entrepreneurship can be deeply rewarding. But building something from scratch is not for the faint of heart, and too often people walk in unprepared, holding onto myths that set them up for failure. If you’re considering taking the leap, it’s important to understand what’s ahead and prepare for the challenges.
One of the first misconceptions people carry into business ownership is the idea that running your own company will give you more free time. They imagine that since they won’t be punching a clock, they’ll have the flexibility to take time off whenever they want. The truth is the opposite. In the early days, your business will consume nearly every waking hour. Long nights, early mornings, and weekends will disappear into tasks that never seem to end.
The time you once reserved for family, hobbies, or rest shrinks quickly. If you’re married or raising kids, this isn’t just your sacrifice—it’s theirs too. Before you launch, you need to have a serious conversation with your spouse or partner. Be upfront that this will mean missed ballgames, skipped family events, and more stress than either of you may expect. If your household isn’t prepared to shoulder that together, the business will suffer.
The Reality of Overhead and Hidden Costs
Another hard truth is how quickly overhead devours revenue. A side gig is flexible—you can pick it up or set it down as life allows. But turning that into a full business introduces an entirely new layer of expenses. Suddenly, you need to think about insurance, payroll, taxes, licensing, marketing, software, and equipment.
The money that looked promising when you were doing things part-time quickly vanishes into overhead. And it doesn’t stop there. As you grow, new layers of cost and complexity appear. A contractor with one truck soon needs a second. A designer working from home eventually needs an assistant or office space. Growth is expensive, and every time you level up, your net income takes a hit until you stabilize again.
Some entrepreneurs save a little money, assume they’ll hire help, and expect revenue to immediately cover the difference. But reality rarely works out that way. Even the best ideas take time to be understood and embraced by customers. You need enough financial cushion to weather storms and setbacks, or you’ll find yourself overloaded with work you can’t pay others to handle.
Choosing the Right Structure
The structure of your business is another factor people underestimate. Should you be a sole proprietor, an LLC, or a corporation? Each option comes with rules, protections, and obligations that will affect you for years to come. It’s tempting to go with the cheapest or simplest choice, but that can leave you exposed.
The best move is to consult multiple professionals, get different perspectives, and choose the structure that fits your goals and industry. Too many entrepreneurs rely on the advice of one person, who may be biased toward the solution they profit from or have limited experience. This isn’t a place to cut corners. Set up your business correctly from the beginning, or you’ll face more headaches down the road.
Branding Beyond Your Inner Circle
Beyond the legal and financial setup comes branding and marketing. Many people start with a skill they enjoy or a product that’s popular among friends. That inner circle provides encouragement and initial sales, but it doesn’t represent the wider market. Once you step beyond friends and family, you’re competing with strangers’ trust, perception, and habits.
That’s where branding becomes essential. Your business name, logo, colors, and messaging must resonate with customers who don’t know you personally. Too often, entrepreneurs design their brand around their own tastes or the opinions of family members rather than their target audience. This leads to frustration, wasted time, and sometimes the painful process of rebranding after realizing the first attempt didn’t work.
Branding isn’t about what you like; it’s about what makes your customers confident in you. If you can’t make that shift, you’ll struggle to gain traction.
Marketing Is Non-Negotiable
Marketing itself is the lifeblood of your business. Once you run out of friends and family to sell to, you need a way to generate consistent visibility and trust. That requires investment—of money, time, and strategy.
Cheap shortcuts rarely work. Templates, do-it-yourself platforms, or bargain freelancers may get you started, but they rarely deliver long-term results. Even worse, many entrepreneurs hire the wrong professionals and end up burned, spending thousands on websites, logos, or campaigns that do nothing to move the business forward.
Good marketing requires patience, constant adjustment, and a willingness to analyze data and make changes. The best results come from a partnership where you and your marketing team work together, reviewing what’s working and what isn’t, and refining over time. It’s not a set-and-forget process, and it’s not cheap, but it is non-negotiable if you want to survive.
Patience Is the Secret Weapon
Patience may be the most underrated requirement for success. Too many entrepreneurs expect immediate results and pull the plug when they don’t see them. Building awareness, trust, and momentum takes time.
Competitors who have been around for years already have reputations, reviews, and loyal customers. It won’t matter if your website looks better; people trust what they know. Breaking into a market requires consistency, visibility, and perseverance. That means staying the course even when the returns feel slow.
Some entrepreneurs supplement limited marketing budgets with sweat equity—knocking on doors, networking tirelessly, and building personal connections. Others save resources to outlast the slow early stages. Either way, patience is the thread that keeps businesses alive long enough to thrive.
Preparing for the Hard Road
All of this may sound discouraging, but it shouldn’t be. These are simply the realities of entrepreneurship. If you walk in expecting long hours, financial strain, endless learning, and slow growth, you’ll be better prepared to handle them. If you enter expecting freedom, instant profits, and smooth sailing, you’ll be crushed by disappointment.
The most successful entrepreneurs aren’t the ones with the flashiest ideas or the most energy. They’re the ones who prepare for the worst, sacrifice willingly, trust the process, and stay the course. They don’t let family opinions dictate their branding, they don’t chase shortcuts, and they don’t panic when the first months are hard. They commit, they adjust, and they endure.
Starting a business can be one of the most gratifying journeys of your life, but it will test your patience, your resilience, and your relationships. It demands sacrifice and persistence. The fantasies that some agencies and do-it-yourself platforms sell you—the idea that success is simple and instant—are illusions. Don’t fall for them.
Understand that what you’re really signing up for is long hours, hidden costs, setbacks, and stress. But if you’re willing to prepare, endure, and persist, the reward can be a business that not only survives but thrives. The difference lies in whether you enter the journey like the overconfident Marine who thought he had it under control, or the one who prepared for the worst and pushed through to success.
ADDITIONAL RESOURCES:
https://explodingtopics.com/blog/startup-failure-stats
https://www.forbes.com/advisor/business/software/startups-failure-rate
https://hbr.org/2021/05/why-start-ups-fail
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Why Your Side Gig Might Not Be Ready | Over the Bull®
Starting a business is one of the most exciting decisions a person can make—and one of the most dangerous. Over the past year and a half, I’ve watched countless people launch new ventures, chase side gigs full time, or dream of leaving their jobs to go out on their own. Some succeed, but many stumble….
Starting a business is one of the most exciting decisions a person can make—and one of the most dangerous. Over the past year and a half, I’ve watched countless people launch new ventures, chase side gigs full time, or dream of leaving their jobs to go out on their own. Some succeed, but many stumble. Others are walking blindly into mistakes that could have been avoided with a dose of reality.
This isn’t meant to discourage ambition. On the contrary, entrepreneurship can be deeply rewarding. But building something from scratch is not for the faint of heart, and too often people walk in unprepared, holding onto myths that set them up for failure. If you’re considering taking the leap, it’s important to understand what’s ahead and prepare for the challenges.
One of the first misconceptions people carry into business ownership is the idea that running your own company will give you more free time. They imagine that since they won’t be punching a clock, they’ll have the flexibility to take time off whenever they want. The truth is the opposite. In the early days, your business will consume nearly every waking hour. Long nights, early mornings, and weekends will disappear into tasks that never seem to end.
The time you once reserved for family, hobbies, or rest shrinks quickly. If you’re married or raising kids, this isn’t just your sacrifice—it’s theirs too. Before you launch, you need to have a serious conversation with your spouse or partner. Be upfront that this will mean missed ballgames, skipped family events, and more stress than either of you may expect. If your household isn’t prepared to shoulder that together, the business will suffer.
The Reality of Overhead and Hidden Costs
Another hard truth is how quickly overhead devours revenue. A side gig is flexible—you can pick it up or set it down as life allows. But turning that into a full business introduces an entirely new layer of expenses. Suddenly, you need to think about insurance, payroll, taxes, licensing, marketing, software, and equipment.
The money that looked promising when you were doing things part-time quickly vanishes into overhead. And it doesn’t stop there. As you grow, new layers of cost and complexity appear. A contractor with one truck soon needs a second. A designer working from home eventually needs an assistant or office space. Growth is expensive, and every time you level up, your net income takes a hit until you stabilize again.
Some entrepreneurs save a little money, assume they’ll hire help, and expect revenue to immediately cover the difference. But reality rarely works out that way. Even the best ideas take time to be understood and embraced by customers. You need enough financial cushion to weather storms and setbacks, or you’ll find yourself overloaded with work you can’t pay others to handle.
Choosing the Right Structure
The structure of your business is another factor people underestimate. Should you be a sole proprietor, an LLC, or a corporation? Each option comes with rules, protections, and obligations that will affect you for years to come. It’s tempting to go with the cheapest or simplest choice, but that can leave you exposed.
The best move is to consult multiple professionals, get different perspectives, and choose the structure that fits your goals and industry. Too many entrepreneurs rely on the advice of one person, who may be biased toward the solution they profit from or have limited experience. This isn’t a place to cut corners. Set up your business correctly from the beginning, or you’ll face more headaches down the road.
Branding Beyond Your Inner Circle
Beyond the legal and financial setup comes branding and marketing. Many people start with a skill they enjoy or a product that’s popular among friends. That inner circle provides encouragement and initial sales, but it doesn’t represent the wider market. Once you step beyond friends and family, you’re competing with strangers’ trust, perception, and habits.
That’s where branding becomes essential. Your business name, logo, colors, and messaging must resonate with customers who don’t know you personally. Too often, entrepreneurs design their brand around their own tastes or the opinions of family members rather than their target audience. This leads to frustration, wasted time, and sometimes the painful process of rebranding after realizing the first attempt didn’t work.
Branding isn’t about what you like; it’s about what makes your customers confident in you. If you can’t make that shift, you’ll struggle to gain traction.
Marketing Is Non-Negotiable
Marketing itself is the lifeblood of your business. Once you run out of friends and family to sell to, you need a way to generate consistent visibility and trust. That requires investment—of money, time, and strategy.
Cheap shortcuts rarely work. Templates, do-it-yourself platforms, or bargain freelancers may get you started, but they rarely deliver long-term results. Even worse, many entrepreneurs hire the wrong professionals and end up burned, spending thousands on websites, logos, or campaigns that do nothing to move the business forward.
Good marketing requires patience, constant adjustment, and a willingness to analyze data and make changes. The best results come from a partnership where you and your marketing team work together, reviewing what’s working and what isn’t, and refining over time. It’s not a set-and-forget process, and it’s not cheap, but it is non-negotiable if you want to survive.
Patience Is the Secret Weapon
Patience may be the most underrated requirement for success. Too many entrepreneurs expect immediate results and pull the plug when they don’t see them. Building awareness, trust, and momentum takes time.
Competitors who have been around for years already have reputations, reviews, and loyal customers. It won’t matter if your website looks better; people trust what they know. Breaking into a market requires consistency, visibility, and perseverance. That means staying the course even when the returns feel slow.
Some entrepreneurs supplement limited marketing budgets with sweat equity—knocking on doors, networking tirelessly, and building personal connections. Others save resources to outlast the slow early stages. Either way, patience is the thread that keeps businesses alive long enough to thrive.
Preparing for the Hard Road
All of this may sound discouraging, but it shouldn’t be. These are simply the realities of entrepreneurship. If you walk in expecting long hours, financial strain, endless learning, and slow growth, you’ll be better prepared to handle them. If you enter expecting freedom, instant profits, and smooth sailing, you’ll be crushed by disappointment.
The most successful entrepreneurs aren’t the ones with the flashiest ideas or the most energy. They’re the ones who prepare for the worst, sacrifice willingly, trust the process, and stay the course. They don’t let family opinions dictate their branding, they don’t chase shortcuts, and they don’t panic when the first months are hard. They commit, they adjust, and they endure.
Starting a business can be one of the most gratifying journeys of your life, but it will test your patience, your resilience, and your relationships. It demands sacrifice and persistence. The fantasies that some agencies and do-it-yourself platforms sell you—the idea that success is simple and instant—are illusions. Don’t fall for them.
Understand that what you’re really signing up for is long hours, hidden costs, setbacks, and stress. But if you’re willing to prepare, endure, and persist, the reward can be a business that not only survives but thrives. The difference lies in whether you enter the journey like the overconfident Marine who thought he had it under control, or the one who prepared for the worst and pushed through to success.
ADDITIONAL RESOURCES:
https://explodingtopics.com/blog/startup-failure-stats
https://www.forbes.com/advisor/business/software/startups-failure-rate
https://hbr.org/2021/05/why-start-ups-fail