The Career Crossroads: Navigating the Choice Between Employment & Entrepreneurship

Picture this: You're suddenly unemployed and there is a blank slate in front of you: a rare opportunity where you can write your OWN future for a change. Which path will you take? Going back to the familiar hell of the 9-5 life, or venturing into 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

In Pursuit of Progress

The biggest career killer? Staying in a dead-end job or a position that’s only holding you back. Whether your manager is checked out, or the company is stagnant, ambition can quickly wither and die.

Before taking action with an exit strategy, take a step back and assess where you are. Take time to assess your situation holistically:

Are you learning?
Are you growing?
Are you feeling part of a community?
Are there issues that can be easily resolved?
Are you getting closer to your long-term goals?
Are there other internal roles that may be a better fit?
Are there other companies and employers that may be a better fit?

Accept that you may be unhappy and that you deserve better. And remember, nothing changes until you make the first move.

Trust your instincts. There are always better opportunities waiting for you, you just have to make the decision to go after them.

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)

Your well-being is crucial, but so is making informed decisions.

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.

Affirm: By accepting the trade-offs to traditional employment I am finding ways to thrive in a flawed system. I can still use my creativity and gifts to help others and make a difference in the world, even if I am also 'working for the Man. I continue to explore future alternatives that are aligned with my soul's purpose.

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.

YOU know yourself better than anyone. Nobody can make this decision for you. Key needs and personal 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 Financial 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 & 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.
Knowledge & 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 of Your Big Transition

Rather than avoiding fear or change in life, consider taking calculated, manageable risks through small actions per day. Tiny low-stakes steps can boost your confidence and resilience so that you can trust the outcome of whatever comes your way or whatever decision to choose.

Define Your Success

Clarify what stability, fulfillment, and growth look like for you to make informed decisions that align with your values. Imagine your dream life in both scenarios: Employment vs Entrepreneurship.

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. Learn in-demand skills (courses, certifications, workshops) 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.

Be careful, but not so careful that you are too afraid to take steps forward.

Expand Your Network

Connect with a trusted and respected mentor, someone experienced in your chosen path for guidance and insight. Explore 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. Network like it's your second job!

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.

Knowledge and education about risk management can empower you to make informed decision that align with your comfort level.

Mitigating the risks 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.

The Hybrid Approach

Remember, You don’t have to commit fully to one path right away. It's usually best to begin your self-employment journey as a side hustle to test the waters and build confidence before fully committing. Use that time to

outline your goals, target audience, financial projections, and marketing strategies to set a clear direction.
Take on side-projects, consult part-time or offer workshops or lead magnets

"If you grew up in survival mode, you learned to adapt, not choose.That’s why capitalism feels familiar—it forces you to make choices that are just different versions of survival.

Andrea Roach

The Bravest Choice

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

Failure often leads to medium rewards or valuable lessons.

Trust your Intuition

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. However 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.

We can't overlook the importance of pure intuition when it comes to making decisions. Your intuition is your gift. It is a quiet, confident inner knowing, a subtle "yes" voice that guides you consistently and gently.

Intuition is a quiet clarity focused on possibilities: It moves you toward something meaningful or aligned, even if it feels slightly uncomfortable.

If something simply doesn't feel good or right, honor that. Practicing mindfulness and self-awareness can help you discern the difference fate and fear.

Is your avoidance a result of unhealed wounds or triggers? Is your ego trying to protect you from something real or imagined?
Follow the choice that feels calm, grounded, expansive or settled, not constrictive, emotional or tense.

Letting go of shame starts with recognizing that TIMING is also 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.

STAY CONNECTED by subscribing or following mebelow and never miss another post related to mindful marketing.

MY WORK

damselfly digital