Last updated on March 23rd, 2025 at 02:54 pm

This article is all about overcoming fear and mindset challenges you may have about starting a business after retirement. You may have been one of those people who wanted to start a business of your own when you were younger.  The problem is that life got in the way.  Career, marriage, kids, graduations, grandkids, etc.  And those life challenges were just the start.  Fear of failing, and fear of not being able to support yourself are perhaps the biggest fears for younger people.  

I have started many businesses before and after retirement.  I know firsthand the anxiety that comes from a mindset that indicates you may fail.  Starting a business after retirement takes you out of your comfort zone making that fear of failure front and center.

 It does not help that often family members are not encouraging.  Lots of people seek comfort and guidance from those who have never had to risk anything to earn a living.  Let’s get the big stuff out of the way by identifying the elephant in the room and directing it:

“You don’t need to be an expert to Start a Business After Retirement”

You can become an expert

Top 20 Fears of Starting a Business After Retirement

Financial Fears

1. Not Having Enough Money – The biggest fear for new entrepreneurs is whether their retirement business idea will generate an income stream that supports their retirement plan and lifestyle.
2. Losing Financial Security – Retirees often fear that investing in their own business could risk their savings, social security, or pension.
3. Unexpected Expenses – Without proper financial planning, many small businesses struggle with hidden costs, which can be a major concern for those on a fixed income.
4. Mismanaging Finances – Without the guidance of a financial advisor, some fear they won’t allocate resources correctly, leading to financial instability.
5. Balancing Work-Life in Retirement – Many retirees worry about maintaining a work-life balance while enjoying their retirement years.
6. Not Making Enough Money – The biggest fear is that the business won’t bring in enough to cover expenses, let alone provide additional income.

Mindset & Self-Doubt

7. Fear of the Unknown – Starting a business in a new phase of life can feel overwhelming because of uncertainties about the market, technology, or legal aspects.
8. Feeling Too Old to Learn New Things – Many worry that they can’t develop the new skills needed to become a successful business owner in their retirement years.
9. Lack of Confidence – Some retirees doubt whether they have the right mindset or knowledge to start a successful business in the first place.
10. Not Knowing the First Step – Many retirees hesitate because they don’t know the best way to launch their business or who to ask for guidance.

Market & Customer Fears

11. Finding Potential Customers – Understanding the target market and reaching prospective customers can feel daunting, especially for retirees unfamiliar with modern marketing.
12. Too Much Competition – Some fear their small business idea won’t stand out in a crowded market.
13. Not Knowing How to Market the Business – New entrepreneurs often feel lost when it comes to branding, social media, and digital advertising.

Operational & Legal Concerns

14. Not Understanding Business Taxes & Legal Issues – Many fear making mistakes with business registration, contracts, or taxes. Seeking help from the U.S. Small Business Administration can be a good thing.
15. Fear of Technology – Many successful entrepreneurs use digital tools, but new entrepreneurs may worry about learning them. The good news is that online courses can help bridge this gap.
16. Writing a Business Plan – Without a solid business plan, retirees fear they won’t have a clear strategy for success.

Personal & Lifestyle Fears

17. Balancing Business with Personal Life – A small step into business ownership can quickly become all-consuming, affecting time with family members and leisure activities.
18. Health & Energy Levels – Many worry that running a consulting business or managing operations will be too exhausting in their stage of life.
19. Losing Personal Fulfillment – Retirees want to maintain a sense of purpose while ensuring their own business aligns with personal interests.
20. Is This the Perfect Time? – Many hesitate, wondering if now is the best thing or if they should wait before taking that first step toward a fulfilling retirement.

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The Good News! 🎉

Overcoming these fears is possible with the right mindset, financial planning, and growth mindset. Many successful entrepreneurs started in their retirement years, proving that this new chapter can be one of the great things in life. Whether it’s a retirement business idea, a consulting business, or an online business, small businesses thrive when planned carefully.

💡 Best Way to Start? Take a small step—talk to a financial advisor, enroll in online courses, and begin crafting your business plan today! 🚀

Now for my discussion of those you should not seek advice from.  This list below is going to hurt a bit because some of your own family members and best friends will attempt to discourage you from starting your own business.  This happened to me when I was younger.  None of my family members started their own businesses, they all had great jobs with pensions.  Many thought I was crazy going it alone.

I found two key reasons for their sentiment.  One was jealousy, lots of people want to start their own business and know they just can’t.  Therefore, you can’t either.  The next reason is that your family may be concerned about your financial welfare or even health.  Great reasons but since they have no experience with owning and managing a business they should not be the ones you confide in. Check out our list:

not everyone gives good business advice, and some may discourage you out of fear, jealousy, or their own financial concerns. Here are the top five people/entities you should NOT ask for business advice when starting a business after retirement:

1. Family Members Who Have Never Started a Business

• Even with good intentions, family members who lack entrepreneurial experience often project their fears onto you.
• They may discourage you due to financial concerns, fear of risk, or jealousy over your ambition.
• Their advice is usually based on job security thinking, not entrepreneurial growth.

2. Friends Who Play It Safe & Avoid Risks

• People who have always worked traditional jobs may see business ownership as too risky.
• Their mindset is often focused on job security, steady paychecks, and avoiding financial uncertainty—which is the opposite of entrepreneurship.

3. Social Media “Gurus” or Unverified Online Coaches

• Many so-called “business experts” on YouTube, Instagram, and TikTok sell courses instead of real advice.
• Their advice is often generic, unrealistic, or designed to make them money—not help them succeed.
• Instead, look for successful entrepreneurs with real business experience and verifiable success.

4. People Who Failed in Business & Blame Others

• Some individuals failed at business due to poor planning and now believe it’s impossible to succeed.
• They often discourage others because they assume everyone will fail like they did.
• Instead, learn from successful entrepreneurs who overcame obstacles.

5. Traditional Bankers & Financial Advisors Who Don’t Work With Small Businesses

• Some financial advisors and bankers only understand corporate finance and traditional investments, not starting a business after retirement.
• They may push you toward safe investments (like mutual funds) and discourage entrepreneurship.
• Instead, work with a financial advisor who is experienced in small businesses and entrepreneurship.

Who Should You Ask for Advice?

✅ Successful entrepreneurs who have built businesses (especially later in life) like the author of this article
✅ Business mentors (from SCORE, the U.S. Small Business Administration, or networking groups).
✅ Industry experts who understand your specific business niche such as the author of this article and RetireCoast
✅ Accountants & financial planners specializing in small business startups.  Be careful here, some do not have expertise.

✅ Read RetireCoast’s full series of articles: Starting a Business After Retirement” which provides extensive help with starting a business after retirement. Included in the series are things we can do to help you including create your business.

Shifting to a Can-Do Mindset: Overcoming Fear & Embracing Business Ownership After Retirement

Starting a business after retirement is a great idea, but for many baby boomers, the fear of change can be a major roadblock. The most common fears—losing financial stability, investing too much time, or struggling with market volatility—often hold people back. However, the right mindset can open doors to new opportunities, providing not only an income source but also a renewed sense of purpose and fulfillment.

The key to success? Changing your mindset from “I can’t” to “I can.” This means acknowledging challenges while embracing positive attitudes and lifelong learning to overcome them. Let’s take a closer look at how to shift from fear to confidence when starting your own company in retirement.

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1. From Fear of Change to Embracing Opportunity

One of the main reasons retirees hesitate to start a new business is the fear of change. Many spent decades in traditional employment, where a job title defined their career. Transitioning to an online business, vacation rentals, or consulting feels unfamiliar.

How to Shift to a Can-Do Mindset:

✅ Reframe change as growth. Instead of fearing uncertainty, see it as an opportunity for lifelong learning.
✅ Start with small steps. A part-time job or freelancing can ease the transition from a day job to business ownership.
✅ Seek guidance. Business mentors and advisory services can help navigate new industries.

Positive Mindset Shift: “This isn’t the end of my career—it’s the best time to create something I truly enjoy.”

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2. From Financial Risk to Smart Planning

Many retirees fear financial risk—investing their savings in a new business could impact their investment portfolio and cash flow. While these concerns are valid, market research and financial planning can reduce risks.

How to Shift to a Can-Do Mindset:

✅ Diversify income sources. Instead of putting all funds into one venture, explore multiple income sources like vacation rentals or an online business.
✅ Consult a financial adviser. Get expert advice on managing market volatility and ensuring long-term stability.
✅ Keep a close relationship with your budget. Monitor expenses and build a cushion before making big financial commitments.

Positive Mindset Shift: “Financial stability comes from smart planning, not avoiding opportunity.”

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3. From Worrying About Too Much Time to Structuring a Daily Routine

One common hesitation is the belief that running a business will take up too much time. However, a well-structured daily routine ensures the right balance between work and leisure.

How to Shift to a Can-Do Mindset:

✅ Create a to-do list. A simple plan keeps business tasks manageable and prevents overwhelm.
✅ Prioritize automation. Many online businesses use automation tools to reduce workload and allow for less time spent on manual tasks.
✅ Think part-time. Running a business doesn’t mean working full-time—you control the schedule.

Positive Mindset Shift: “I don’t have to work 40+ hours to have a successful business; I can work smarter, not harder.”

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4. From Doubt to a Strong Business Foundation

Some retirees believe they lack the skills to succeed in new businesses, leading to self-doubt and procrastination. The reality? Many successful careers have transferable skills that apply to business ownership.

How to Shift to a Can-Do Mindset:

✅ Leverage past experience. Decades in a corporate role, sales, or management provide valuable skills for running a business.
✅ Learn new strategies. Taking market research and business development courses can strengthen confidence.
✅ Surround yourself with entrepreneurs. A support network of business owners can provide practical advice and motivation.

Positive Mindset Shift: “I already have valuable experience—I just need to apply it in a different way.”

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5. From Fear of Failure to Seeing Setbacks as Learning Experiences

Many retirees fear making mistakes, but successful entrepreneurs understand that failure is part of the journey.

How to Shift to a Can-Do Mindset:

✅ View setbacks as data. Every misstep provides insights that improve the business.
✅ Focus on small wins. Celebrate progress, even if it’s just launching a website or making the first sale.
✅ Remember: The best choice is the one you commit to. No business is risk-free, but commitment leads to results.

Positive Mindset Shift: “Every great business started with trial and error—mine is no different.”

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The Power of the Can-Do Mindset

Fear is normal, but your own fear should never stop you from achieving something meaningful. Shifting to a positive, can-do mindset helps turn fear into action, doubt into confidence, and challenges into opportunities.

Whether you’re starting an online business, a consulting firm, or investing in vacation rentals, this new phase of life can be the most rewarding yet—if you embrace it with the right mindset.

💡 Best Time to Start? Right now. Take that small step today! 🚀

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Use our Work-life Balance Tool as a courtesy of RetireCoast.com and part of our extensive series on “Starting a Business After Retirement”

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Becoming an Expert in Your Business After Retirement: The Key to Confidence and Success

One of the biggest fears retirees face when starting a business is not feeling like an expert in their chosen field. But here’s the good news: You don’t need to be an expert to start—you just need to commit to becoming one.

Many successful entrepreneurs began with little knowledge in their industry, but by immersing themselves in learning and hands-on experience, they built confidence, credibility, and success. The process of becoming an expert helps overcome fear and doubt while shifting to a positive, can-do mindset that fuels business growth.

Let’s take a closer look at how you can become an expert in your chosen business—even if you’re starting from scratch. The example below is for someone who is creating a landscaping business after retirement. Most of the recommendations will apply to any business.

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Starting a Landscaping Business

1. Work with an Expert in the Field

One of the fastest ways to gain real-world knowledge is by working with someone who’s already established.

✅ Offer to shadow a professional – If you’re starting a landscaping business, spend time with an experienced landscaper to observe their work.
✅ Take a part-time job or internship – Even if unpaid, working in the field helps you gain hands-on experience.
✅ Ask to apprentice – Many small business owners are open to mentoring if you express a willingness to learn.

💡 Mindset Shift: “I don’t have to figure everything out alone—I can learn from those who have already succeeded.”

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2. Conduct Deep Market Research

To be seen as an expert, you need to understand the industry inside and out.

✅ Scour the internet for knowledge – Read articles, watch YouTube tutorials, and follow industry blogs.
✅ Take online courses – Platforms like Coursera, Udemy, and LinkedIn Learning offer affordable business and technical courses.
✅ Stay updated on industry trends – Subscribe to landscaping magazines, follow garden influencers, and engage in Facebook groups or forums.

💡 Mindset Shift: “Becoming an expert is just about learning more each day than I knew yesterday.”

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3. Talk to People with Expertise

The best way to gain insider knowledge is by speaking directly to those who already know the business.

✅ Visit garden centers and nurseries – Ask about different plants, trees, and seasonal lawn care.
✅ Network with professionals – Connect with landscape designers, irrigation specialists, or soil experts.

✅  Read RetireCoast’s Series: Starting a Business After Retirement
✅ Attend industry events and expos – Trade shows and local meetups provide valuable networking opportunities.

💡 Mindset Shift: “The more I learn from experienced people, the faster I grow into an expert myself.”

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4. Gain Hands-On Experience

Reading about business is great, but nothing replaces real-world practice.

✅ Start with small projects – Practice landscaping your own yard or help a friend.
✅ Offer free or discounted services – Build a portfolio by working with neighbors or community members.
✅ Document your learning journey – Take photos, make notes, and track your progress.

💡 Mindset Shift: “The best way to become an expert is by doing, not just studying.”

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5. Teach Others What You Learn

One of the best ways to reinforce your expertise is by teaching others.

✅ Start a blog or YouTube channel – Share what you’re learning about landscaping.
✅ Host workshops or webinars – Teach community members about lawn care, plant maintenance, or sustainable gardening.
✅ Mentor new business owners later – Once you’ve built experience, help others start their own businesses.

💡 Mindset Shift: “If I can teach it, I truly understand it.”

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How Becoming an Expert Overcomes Fear & Builds Confidence

Fear often comes from uncertainty and lack of knowledge. By actively working toward expertise, you remove doubts and replace them with confidence and control.

✅ Fear of not knowing what to do? → Learning removes uncertainty.
✅ Fear of failing? → Expertise makes you better prepared for challenges.
✅ Fear of competition? → Your knowledge will make you stand out.
✅ Fear of not making enough money? → Expertise leads to better service, more customers, and higher earnings.

💡 Final Mindset Shift: “The more I invest in learning, the more I invest in my success.”

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The Best Time to Start is Now!

If you feel like you’re not an expert yet, that’s okay—every successful entrepreneur started as a beginner. By taking small, consistent steps to gain experience, learn from others, and apply what you know, you’ll quickly become the expert that your customers trust.

Learning Plan for Starting a Landscaping Business

📅 Duration: 6-12 months (Adjustable based on time availability)
🎯 Goal: Gain the knowledge, skills, and hands-on experience needed to start and grow a successful landscaping business.

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📍 Phase 1: Foundational Learning (1-2 Months)

Objective: Build a strong understanding of landscaping principles, tools, and industry knowledge.

✅ Step 1: Research the Landscaping Industry

• Read books such as Landscaping for Dummies or The Essential Landscaping Guide.
• Follow landscaping blogs and YouTube channels like This Old House and Garden Answer.
• Subscribe to trade magazines like Lawn & Landscape or Total Landscape Care.

✅ Step 2: Take Online Courses (Choose at least one)

• Udemy: “Professional Landscaping Design & Maintenance”
• Coursera: “Sustainable Landscaping & Garden Design”
• LinkedIn Learning: “Landscaping Fundamentals for Beginners”

✅ Step 3: Learn About Plants & Lawn Care

• Visit local garden centers and ask experts about soil types, grass varieties, and seasonal care.
• Study native plants and trees suitable for your local climate.
• Research common pests, weeds, and lawn diseases and their treatments.

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📍 Phase 2: Hands-On Training (2-4 Months)

Objective: Gain real-world experience by working with professionals and practicing on small projects.

✅ Step 4: Work with a Landscaping Company (If Possible)

• Apply for a part-time job, internship, or apprenticeship with a local landscaping business.
• Shadow professionals to learn about design, irrigation, equipment, and client management.
• Ask questions and take notes on business operations.

✅ Step 5: Start Small Projects on Your Own

• Offer free or discounted landscaping work for friends, family, or neighbors.
• Work on your own lawn or garden and document progress.
• Experiment with mulching, pruning, edging, and laying sod.

✅ Step 6: Master Landscaping Tools & Equipment

• Learn how to properly use mowers, trimmers, blowers, aerators, and edgers.
• Understand maintenance and safety procedures for each tool.

✅ Step 7: Attend Industry Events & Network

• Go to landscaping expos, trade shows, or local workshops.
• Join Facebook groups, forums, or LinkedIn groups for landscapers.
• Connect with suppliers, garden centers, and real estate professionals.

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📍 Phase 3: Business & Marketing Prep (2-3 Months)

Objective: Learn how to run the business, attract customers, and set up legal & financial systems.

✅ Step 8: Develop a Business Plan

• Define your services: Lawn care, garden design, irrigation, maintenance, etc.
• Research pricing strategies by checking local competitors.
• Identify your target market (residential, commercial, property managers, realtors, etc.).

✅ Step 9: Learn Business & Financial Basics

• Take a basic bookkeeping course to track income and expenses.
• Read RetireCoast’s series on Starting a Business After Retirement
• Meet with a financial adviser to discuss budgeting and cash flow.
• Understand business insurance and liability protection for landscapers.

✅ Step 10: Market Your Business

• Build a simple website showcasing your work, pricing, and contact info.
• Create a Google My Business profile and get listed in local directories.
• Start a Facebook & Instagram page and post before/after landscaping photos.
• Offer promotions to attract first-time customers.

📍 Phase 4: Launch & Scale (Ongoing)

Objective: Start taking on clients, refining skills, and growing the business.

✅ Step 11: Get Licensed & Insured

• Research if your state/city requires a landscaping business license.
• Obtain necessary liability insurance to protect yourself.

✅ Step 12: Get Your First Clients

• Reach out to friends, family, and neighbors for referrals.
• Offer seasonal specials or discounts to attract new clients.
• List services on Facebook Marketplace, Craigslist, and Nextdoor.

✅ Step 13: Continue Learning & Expanding

• Upskill in landscape design, irrigation systems, and hardscaping.
• Explore add-on services like tree trimming, pest control, or snow removal.
• Consider hiring seasonal workers or subcontractors as the business grows.

✅ Step 14: Contract Experienced Help

• Find a landscaper with industry experience who can guide you.
• Be upfront: Explain that it’s temporary, but you want to learn from them while getting started.
• If the business takes off, offer them a permanent role or higher-paying work as a team member.
• Use their expertise to fine-tune your techniques, pricing, and client management strategies.

💡 Mindset Shift: “Learning from an expert in the field will speed up my success and make my business more professional from day one.”

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Summary

Planning, planning, planning. I can not say this enough. The primary fear is that of the unknown. Why not eliminate as much of the unknown as possible? As this article indicates, create a business plan and a marketing plan. Creating these documents is not difficult with our help. Click on each of the plans above which will take you to our individual articles on the topics.

You will find templates and other tools to help you create your business and marketing plans even if you have never done this before. The research that goes into creating the plans will chip away at that unknown iceberg. Listen to our podcasts which are often based upon our articles about Starting A Business After Retirement.