From 9-5 to Entrepreneur: Transition Guide
- Jackie Johnson
- Feb 27
- 9 min read
Updated: Feb 28
Key Steps to Transition:
- Assess Readiness: Evaluate your skills, strengths, and risk tolerance.
- Build Financial Security: Save 6–12 months of living expenses and secure health insurance.
- Create a Business Plan: Define your business model, market research, and measurable goals.
- Start Small: Work on your business while employed, test your ideas, and grow gradually.
- Set Up Tools: Use no-code platforms, AI tools, and a CRM system to streamline operations.
- Plan Exit Strategy: Transition out of your job only when your business generates stable income.
Quick Tips:
- Save a financial cushion to cover personal expenses.
- Research your market and competitors thoroughly.
- Start with a Minimum Viable Product (MVP) to test your idea.
- Use tools like Bubble, Notion AI, and Reclaim.ai to save time and money.
- Join business communities for support and mentorship.
Pro Tip: Don’t quit your day job until your business earns at least 75% of your current salary.
This guide breaks down each step in detail, so you can confidently move toward entrepreneurship.
If You Have a 9 to 5 Job, Do This NOW
Check If You're Ready to Start a Business
Making the leap from a 9-to-5 job to running your own business requires preparation. Start by assessing your skills to identify what you're good at and where you might need improvement.
List Your Current Skills and Experience
Begin by listing the technical and interpersonal skills that are relevant to entrepreneurship.
Skill Category | Focus Area | How to Measure |
Hard Skills | Technical expertise, industry knowledge, tools proficiency | Certifications, years of experience, project results |
Soft Skills | Leadership, communication, problem-solving | Peer feedback, performance reviews, client testimonials |
Business Acumen | Financial knowledge, strategic planning, market understanding | Past successes, revenue impact, completed initiatives |
"Critical skills are those most closely linked to strategic business challenges, they're the skills your organization needs to help it transform and stay ahead in the future, rather than just perform day-to-day operations."
Look at job descriptions for roles similar to the business you want to start. Evaluate your skills against these requirements and plan how to improve any areas that are lacking.
Once you've mapped out your strengths and weaknesses, use a SWOT analysis to deepen your understanding of your position.
Complete Your SWOT Analysis
A SWOT analysis helps you identify your business's strengths and weaknesses while also pointing out market opportunities and potential threats.
"A SWOT analysis is useful so that you don't get caught entirely off-guard. You [should] do a SWOT analysis for each application area you're considering operating in."
- Strengths: Internal advantages like specialized skills, valuable industry connections, or intellectual property.
- Weaknesses: Gaps in skills, limited resources, or lack of experience that might hold you back.
- Opportunities: Market needs, new trends, or changes in regulations that could work in your favor.
- Threats: Competitors, market instability, or economic challenges that could pose risks.
"It's vital to go through your analysis with key stakeholders. When you identify weaknesses, it's a great time to get other department heads and staff to suggest solutions - you'll be amazed at the creativity and problem-solving inherent in your team if they are given the opportunity [for] input."
Measure Your Risk Comfort Level
Understanding your risk tolerance is key to determining if you're ready for entrepreneurship. This includes both your emotional comfort with risk and your financial ability to handle it.
"People tend to focus just on their comfort level with risk. But your to take risks based on your financial situation is just as important."
Use the table below to assess your readiness:
Risk Factor | What to Evaluate | Baseline Requirement |
Financial Cushion | Emergency savings | 6-12 months of living expenses |
Income Stability | Dependable revenue streams | Multiple planned income sources |
Health Coverage | Insurance options | Secured independent coverage |
Legal Protection | Contract terms | No restrictive clauses |
Support Network | Professional and personal connections | Active mentors and advisors |
Your ability to take risks may shift over time, but your comfort with uncertainty is often more stable. Build systems and safeguards that align with your risk profile while setting yourself up for success.
Set Up Your Financial Safety Net
Before diving into your business venture, it's crucial to establish a solid financial base to help you navigate the transition smoothly.
Build Your Safety Fund
Set aside enough savings to cover 6–12 months of living expenses. Store this fund in a high-yield savings account separate from your business finances to avoid mixing personal and professional funds.
Expense Category | Monthly Cost | Annual Total |
Housing (rent/mortgage) | $1,500–$3,000 | $18,000–$36,000 |
Healthcare premiums | $450–$850 | $5,400–$10,200 |
Living expenses | $2,000–$4,000 | $24,000–$48,000 |
Emergency buffer | $500–$1,000 | $6,000–$12,000 |
Secure Health and Business Insurance
A strong financial safety net includes proper insurance. Look into health insurance options through Healthcare.gov, professional organizations, local Chambers of Commerce, or health-sharing ministries. For your business, a Business Owner's Policy (BOP) is often a smart choice. It typically combines general liability, property protection, and business income insurance.
"Every business has different needs, and no financial solution is one-size-fits-all. Your personal financial situation and vision for your business will shape the financial future of your business." – U.S. Small Business Administration
Find Business Funding Sources
Launching a business often requires a mix of funding sources. Here's a breakdown of common options:
Funding Method | Usage Rate | Best For |
Self-funding | 73% | Full control, avoiding debt |
Friends & Family | 24% | Quick access, flexible arrangements |
Credit Unions | Usage up 50% (2017–2021) | Lower rates than traditional banks |
Online Lenders | 43% of medium/high-risk applicants | Fast approval, lenient criteria |
Here’s how to approach funding based on your business needs:
- Self-funding: Cut costs by using virtual offices, hiring freelancers, and utilizing no-code tools or automation.
- External Funding: Consider SBA-backed loans if you have a strong credit profile, crowdfunding for consumer-focused products, or angel investors if your business has high growth potential.
Once you’ve secured the necessary funding, you’ll be ready to move forward with confidence and focus on building your business.
Write Your Business Plan
Once your finances are in place, it's time to create a clear business plan. This document will guide your journey from employee to entrepreneur. As the U.S. Small Business Administration puts it, "Your business plan is the foundation of your business" .
Choose Your Business Model
Pick a business model that aligns with your goals and taps into market opportunities. Here are some common options based on your target audience:
Business Model | Best For | Key Revenue Source |
Subscription | Ongoing services | Monthly/annual fees |
E-commerce | Selling products | Product sales |
Service-based | Offering expertise | Hourly/project rates |
Marketplace | Connecting buyers and sellers | Transaction fees |
SaaS | Software solutions | Tiered subscriptions |
Before settling on a model, focus on addressing specific customer problems. As Indeed.com highlights, "Business plans are key to the creation, growth, and success of a company. It is a blueprint for the future, a clear outline of how you plan to reach your goals" .
Research Your Market
Validate your chosen business model by gathering detailed market insights. Focus on these three areas:
- Customer Research: Talk to potential customers to understand their needs and challenges.
- Competitive Analysis: Examine what your competitors offer and how they price their products or services.
- Market Size: Estimate your total addressable market (TAM) to gauge the opportunity.
"Avoid choosing a business model until you know more about your target market and your unique solution. If you dive in determined to follow an exact business model, you might miss clues and insights that could lead you in a different (more appropriate) direction."
Use this framework to track your competitor analysis:
Analysis Area | Direct Competitors | Indirect Competitors |
Target Market | Same audience | Different audience |
Price Points | Similar range | Alternative solutions |
Value Proposition | Similar benefits | Different approach |
Distribution Channels | Same methods | Various methods |
Set Business Targets
Based on your market research, define clear and measurable goals. Break them down into these key areas:
Timeframe | Financial Targets | Growth Metrics | Customer Goals |
3 months | Break-even point | 100 leads/month | 20% conversion rate |
6 months | $10,000 monthly revenue | 500 website visitors | 50 active customers |
12 months | $100,000 annual revenue | 25% market share | 90% retention rate |
Regularly review and adjust your plan as you gain new insights. For a quick planning process, try a lean startup approach to outline the essentials in about an hour . If you need funding or a more detailed roadmap, go for a comprehensive business plan.
Pick Your Business Tools and Software
Choosing the right digital tools can make starting your business much smoother. Here's a breakdown of essential software to help you manage and grow your business effectively.
Build Without Code
No-code tools let you create apps and platforms without needing to write code. Check out these popular options:
Tool | Best For | Starting Price | Key Feature |
Bubble | Web Apps | $32/month | Visual Programming |
Softr | Client Portals | $59/month | Airtable Integration |
Glide | Mobile Apps | $60/month | Spreadsheet-Based |
WeWeb | Complex UIs | $49/month | Advanced Design |
Xano | Backend Systems | $100/month | Scalable Infrastructure |
"No-code doesn't mean no work."
Start by creating two projects: one for your actual business app and another for testing and learning the platform . Once your app is up and running, consider using AI tools to boost productivity.
Use AI Tools for Efficiency
AI tools can simplify your workflow and save time. Here are some great options for new entrepreneurs:
Category | Recommended Tool | Monthly Cost | Primary Benefit |
Task Management | Motion | $19 | Smart Scheduling |
Content Creation | Notion AI | $8/user | Document Generation |
Communication | Claude 3.5 | $20 | Advanced Chat |
Scheduling | Reclaim.ai | $8/seat | Calendar Automation |
Presentations | Gamma | $8/user | AI-Powered Slides |
Introduce one AI tool at a time to avoid overwhelming your workflow and to ensure you fully understand its benefits.
Set Up Your CRM System
A CRM system helps you manage leads and customer relationships effectively. Look for a solution that fits your business type and future goals. Start with basic features like contact management and simple automation. As your business grows, you can expand to include advanced options like marketing tools and analytics. The right CRM will evolve with your needs, making it easier to stay on top of customer interactions and sales.
Start Your Business While Employed
Starting a business while holding down a full-time job requires thoughtful planning. It’s all about balancing your current responsibilities while laying the groundwork for your new venture.
Plan Your Exit Timeline
Set a clear timeline for when and how you’ll transition from being an employee to running your own business. This timeline should align with your earlier assessment of risk tolerance.
Timeline Phase | Key Actions | Target Goals |
Months 1-3 | Research and Planning | Complete your business plan and market research |
Months 4-6 | Initial Setup | Register your business and open dedicated bank accounts |
Months 7-9 | Product/Service Launch | Gain your first paying customers and kick off operations |
Months 10-12 | Growth and Transition | Hit your monthly revenue goals and prepare to resign |
Use scheduling tools like Google Calendar to divide your time between your job and business tasks effectively .
Join Business Communities
Connecting with other founders can provide valuable advice and support. A strong professional network can help you navigate challenges and stay motivated.
For example, MakerThrive offers resources such as:
- Private community access
- 30+ recorded workshops
- Live workshop sessions
- Bi-weekly office hours
- A library of over 50 learning materials
Setting clear work hours for your startup tasks can help you avoid burnout .
Handle Legal and Tax Setup
Make sure your business complies with legal requirements while respecting your current employment obligations. Just like financial planning, legal preparation is crucial for a smooth transition.
Here are some key legal steps to take:
- Review your employment contract for any restrictions on side work
- Check for non-compete clauses or NDAs
- Avoid using your employer’s resources for your business
- Choose the right business structure
- File necessary documents with state authorities and submit the BOI report to FinCEN
From the start, keep detailed financial records and use separate accounts for business expenses .
It’s a good idea to consult an employment law attorney to fully understand your rights and obligations. Being upfront with your employer about your plans can help ensure you stay within company policies .
Conclusion: Your Next Steps
Once you've established a solid base for your business, it's time to finalize your plans and take action.
Key Steps to Focus On
Shifting from being an employee to running your own business requires careful planning. Here's a breakdown of essential phases:
Phase | Key Actions | Success Indicators |
Assessment | Conduct a SWOT analysis | Clear view of your strengths and gaps |
Financial Planning | Build an emergency fund | Enough to cover monthly expenses |
Business Setup | Register and insure your business | Compliance with legal requirements |
Market Testing | Launch a Minimum Viable Product (MVP) while employed | Secure your first paying customers |
Full Transition | Implement your exit strategy | Achieve 75% of your current salary in revenue |
Take Action Now
Start building your business with these practical steps:
- Lay the GroundworkUse an entrepreneur's startup checklist from MakerThrive's resource library to stay organized while still employed.
- Find Your TribeJoin communities like MakerThrive to connect with like-minded entrepreneurs. Members gain access to:
- Over 50 learning resources
- Live workshops
- Bi-weekly office hours
- Networking opportunities with seasoned founders
- Set Clear GoalsEstablish revenue milestones before quitting your job. Thomas Aronica, founder of Biller Genie, offers this valuable insight:"Handling money incorrectly and being irresponsible with cash flow is a death sentence for startups with limited access to capital"
To avoid becoming part of the 55% of businesses that fail within five years , focus on creating a strong financial base and clear growth targets before making the leap.