Picture this: You're unemployed and there is a blank slate in front of you, one where you can write your own future. Which path will you take? The familiar hell of the 9-5 office, or the terrifying unknowns of self-employment.
For millions of creative professionals, going back to a job, or starting their own business is the Ultimate Career Dilemma. But not everyone is on the same playing field. For many, the risks are far too great.
In this post I'll break down both the benefits and the challenges of each path to help guide your decision.
“Timing, perseverance, and ten years of trying will eventually make you look like an overnight success.”
Biz Stone
A Birds Eye View
1099 Independent Contractor | W2 Employee |
Project-Based Work Flexibility No withheld taxes Self-employment taxes No PTO or insurance benefits | Structured, Hierarchical Work Stable income Less autonomy Tax withholdings Employee benefits (PTO, health insurance etc) |
Traditional Employment
Pros:
Stability & Security: With a regular paycheck, benefits (health insurance, retirement plans, etc.), and job security (depending on the industry), traditional employment provides a sense of financial stability.
Clear Structure: The work environment is typically more structured, with defined hours, responsibilities, and a hierarchy, which can provide clarity and support.
Teamwork & Networking: Opportunities to collaborate with others, develop relationships, and grow within an organization can lead to career advancement.
Professional Development: Many companies offer training programs, mentorship, and resources for career growth, which can be a valuable way to build your skills.
Cons:
Limited Flexibility: There are typically fixed working hours and locations, which can limit personal freedom and work-life balance.
Lack of Control: You have less control over the direction of the company or your role. Corporate policies or decisions outside of your control may affect your job. Economic downturns or company restructuring can also lead to layoffs, leaving you vulnerable to sudden unemployment.
Potential for Stagnation: Career growth in a traditional job can sometimes be slow, and promotions might be based on factors outside of your immediate influence.
Workplace Dynamics: Office politics, interpersonal conflicts, or unfulfilling tasks can detract from job satisfaction.
Burnout: The structure and demands of traditional employment can sometimes lead to stress or burnout if not properly managed.
"Life is inherently risky. There is only one big risk you should avoid at all costs, and that is the risk of doing nothing."
Denis Waitley
Self-Employment
Pros:
Autonomy: You have complete control over your schedule, projects, and business decisions. This allows you to shape your work around your values and interests.
Flexibility: You can decide when and where to work, which can enhance your work-life balance.
Unlimited Earning Potential: The more successful your business is, the greater your income potential. You aren’t limited by a salary cap.
Personal Fulfillment: If your self-employment is in a field you're passionate about, the sense of purpose and satisfaction can be much higher than in traditional employment.
Cons:
Income Instability: Self-employment often comes with periods of feast and famine, where income can fluctuate. This can make financial planning more challenging. If your business fails or doesn’t generate enough revenue, you could face financial hardship.
No Employee Benefits: You’ll have to handle your own health insurance, retirement savings, and other benefits, which can be time-consuming and costly.
Isolation: Working alone can be isolating, and you might miss out on the social aspects of being part of a team or organization.
Increased Responsibility: You’re responsible for every aspect of your business, including marketing, accounting, and managing clients or customers. This can be overwhelming without the right support systems.
Work-Life Imbalance: While there’s flexibility and freedom, the burden of being responsible for all aspects of your business can lead to overwork and burnout. The lines of professional and personal will be blurred if boundaries are not set.
Uncertainty: There’s often a degree of unpredictability in self-employment, from market trends to customer demands, which can be stressful for some.
"I’m a greater believer in luck, and I find the harder I work, the more I have of it.”
Thomas Jefferson
Considerations for Your Decision
When deciding between traditional employment and self-employment, assessing your core values and priorities can help clarify which path aligns best with your priorities. Reflecting on these values can help you choose the path that best aligns with your long-term goals, personality, and lifestyle preferences.
Key needs and preferences to consider:
Risk/Uncertainty/Fluctuations VS Stability/Security/Predictability
Flexibility/Autonomy/Freedom/Control VS Structure/Routine/Direction/Clarity
Creativity/Innovation VS Consistency/Reliability
Personal Impact VS Large Scale Impact
Personal Growth/Accountability VS. Group Security/ Protection
Work-Life Integration VS Separation
Independent/Solo Work VS Community/Team/Leadership Support
Your Individual Risk Tolerance
How comfortable are you with financial fluctuations?
Long-Term Goals
Where do you see yourself in the next 5-10 years? Do you envision growing a business/brand or would you prefer advancing in a corporate structure?
Skills & Resources
Do you have the necessary skills, network, and savings to succeed in self-employment, or would you benefit from the structures and systems available in a traditional role?
Your Calling
Notice your authentic emotional responses when thinking about each option.
Which path feels more exciting or meaningful?
Does one option feel like a compromise or driven by fear rather than genuine interest?
“The hardest thing to learn in life is which bridge to cross and which to burn.”
David Russell
Risk vs Reward
"You miss 100% of the shots you don’t take." – Wayne Gretzky
"A ship in harbor is safe, but that is not what ships are built for." – John A. Shedd
"Only those who dare to fail greatly can ever achieve greatly." – Robert F. Kennedy
"The person who risks nothing, does nothing, has nothing, is nothing, and becomes nothing." – Leo F. Buscaglia
Clearly, society glorifies risk-takers as courageous leaders. And that may be true, but it can lead to shame for those of us who operate with a preference or bias towards safety and security. There are so few quotes out there on living cautiously, making measured decisions and preparing diligently!
From a patriarchal viewpoint, risk is highly valued. In reality, Risk is a complicated thing. Everyone has a different comfort zone, especially those in marginalized groups.
Aversion to risk varies significantly due to variety of psychological, genetic, and environmental factors. Understanding these factors can help explain the diverse ways individuals approach risk in various aspects of life, including finance, health, and personal relationships.
Personality: Certain personality traits, such as neuroticism and conscientiousness, can influence how individuals approach risk. Those with higher levels of anxiety and overthinking patterns may be more likely to avoid risks. Genetics can play a role in risk tolerance also. Some people may be predisposed to be more cautious based on their genetic makeup.
Past Trauma: Individuals who have experienced negative outcomes from taking risks in the past may become more cautious in the future. Conversely, those who have had positive experiences may be more willing to take risks.
Cultural Influences: Different cultures have varying attitudes toward risk. Some cultures may encourage risk-taking and innovation, while others may prioritize caution and stability.
Economic and Social Privileges: People’s financial situations and social environments can affect their willingness to take risks. Those with more to lose may be more risk averse, while those in more secure positions may feel freer to take chances.
Education: People who are more informed about the potential outcomes of risks may feel more confident in their ability to manage them, leading to a greater willingness to take risks.
If you fall into the population that prioritizes thoughtful and deliberate decision-making and shies away from risk, that's ok! Being risk averse, controlling your circumstances and focusing on long-term goals and stability has several advantages, including greater financial security and planning, lower stress levels, inner peace and psychological safety.
Stop comparing yourself to others. Instead of internalizing the cultural narrative and viewing risk aversion as a weakness, consider it a strength that allows you to make informed decisions and create a life around safety and careful planning
Reminder: Taking risks is not the only path to success. You can find a balance that allows you to feel confident in your decisions while still being true to yourself.
Mitigating Risk
Knowledge and education about risk management can empower you to make informed decision that align with your comfort level.
Mitigating the risks and dangers of both traditional employment and self-employment requires strategic planning, self-awareness, and proactive decision-making. By actively planning for challenges and staying adaptable, you can reduce the risks associated with either path and increase your chances of long-term success.
Define Your Success
Clarify what stability, fulfillment, and growth look like for you to make informed decisions that align with your values.
Build a Safety Net
Employment: Save at least 3–6 months’ worth of living expenses to cushion against potential job loss or layoffs. Start a small side hustle or freelance gig to generate supplemental income and develop skills outside your primary role.
Entrepreneurship: Save 6–12 months of living expenses to account for fluctuating income and initial business setup costs. Use accounting software to track income and expenses. Create a budget to manage irregular income effectively. Avoid relying on a single client or project by developing multiple income streams to stabilize cash flow.
Upskill Continuously
Regularly assess your career goals and industry trends. Consider certifications or education that align with potential future opportunities.
Employment: Stay competitive by developing new skills, earning certifications, and keeping up with industry trends to increase your employability.
Entrepreneurship: Continuously improve your skills and stay updated on market trends to remain competitive and relevant.
Expand Your Network
Connect with a mentor, someone experienced in your chosen path for guidance and insight.
Connect with individuals on both sides of the fence - those who are thriving in traditional roles and those who are successfully self-employed to learn more about their challenges, rewards, and daily realities.
Employment: Cultivate relationships beyond your current workplace to create opportunities for future roles and build a safety net.
Entrepreneurship: Join professional organizations or networking groups for advice, collaboration, and emotional support.
Set Boundaries
Invest in self-care, stress management, and a healthy lifestyle to stay resilient regardless of your career choice.
Employment: Protect yourself from burnout by maintaining work-life balance. Communicate boundaries clearly and manage your workload effectively.
Entrepreneurship: Delegate/outsource tasks like bookkeeping, marketing, or IT to professionals to focus on your core work and prevent burnout and the complete integration of work life.
Protect Yourself
Cultivate adaptability and flexibility to pivot when opportunities or challenges arise.
Employment: Familiarize yourself with labor laws, your employment contract, and your company’s policies to ensure fair treatment.
Entrepreneurship: Consider health, liability, and business insurance to protect yourself from unforeseen expenses or legal issues.
Push Your Limits
Avoiding risks altogether can limit your personal growth and hinder opportunities. Rather than avoiding ALL risk, consider taking calculated, manageable risks. Focus on taking small actions per day to build momentum.
Consider exploring low-stakes, high-adrenaline "risky" activities to boost your confidence and resilience, shifting your locus of control to internal rather than external factors
New hobbies
New networking
Taking a new course
Ice baths
Motorcycle riding
Solo travel
Be careful, but not so careful that you are too afraid to take steps forward.
Laying the Foundation for Self-Employment
There is no way around it: Entrepreneurship is a bigger risk AND will require more work upfront. However the opportunity for greater satisfaction, meaning and fulfillment is greater as it allows you to directly benefit from your hard work and creativity without the limitations of a fixed salary.
It's hard to beat the payoffs
the autonomy to choose projects that align with your energy, passions and values
the potential for unlimited income growth
the flexibility to design your schedule
the chance to build something uniquely yours, with a sense of ownership and pride
If you want to challenge your risk aversion, begin with small, manageable risks. Gradually increasing your exposure to risk can help build confidence. Here are some ways to lay a solid foundation for your entrepreneurial journey, when and if you're read to take it:
Explore a Hybrid Approach. You don’t have to commit fully to one path right away. Begin your self-employment journey as a side hustle to test the waters and build confidence before fully committing.
Outline your goals, target audience, financial projections, and marketing strategies to set a clear direction.
Build a strong online presence and network to attract new clients consistently. Invest time and money into branding and outreach.
Failure often leads to medium rewards or valuable lessons.
Timing is Everything
Still feeling stuck or lost? Feeling a deep curiosity and pull toward self-employment is ultimately a sign of your ambition, creativity, and desire for autonomy.
If now doesn’t feel like the right time to "bet on yourself", that's ok. It doesn't mean you're less courageous or capable than those who are. It means you’re practicing caution and discernment, acknowledging your needs, energy and intuition.
Letting go of shame starts with recognizing that timing is a critical part of success. Your dream isn’t diminished by waiting; it’s being nurtured until you’re ready to pursue it with more confidence, resources and resilience. You’re still setting yourself up for long-term success if you decide to press pause.
Sometimes your intuition can provide clarity when logic fails. Get quiet and go inward to figure out when and where to go, or stay.
Wrapping It Up
Recognize that both entrepreneurship and employment come with uncertainties and unknowns, and there’s no perfect choice. Try to focus on what excites you about each option rather than being paralyzed by the risks. Even if you’re unsure, movement itself creates clarity.
Trust that you’ll adapt and grow and make it through no matter which path you choose. Also know that your decision doesn’t have to be permanent and you can change course at any point!
Ultimately you can't go wrong as long as you're aligned with your authentic self, working towards your goals, and ready to step out of comfort zones when it matters most.
"He who has a Why to live can bear almost any How."
Friedrich Nietzsche
Erin Ratliff is a holistic, organic growth + visibility business coach and consultant serving energy-sensitive soul-preneurs, heart-led self-starters with the mission of personal and planetary healing.
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