How to Start a Business After Retirement: A Step-by-Step Guide

Why Retirement is the Perfect Time to Launch a Business

Retirement isn't the end - it's a wide-open door to something new. For a growing number of Americans, that "something" is entrepreneurship.

A 2023 Kauffman Foundation report found that 26% of all new entrepreneurs are between 55 and 64. More than one in four new businesses are started by people who once thought they were "done" with work. But retirement today looks a lot different than it did a generation ago.

For many, this stage of life is less about winding down and more about finally doing work that feels meaningful, flexible, and aligned with their values. The reasons are obvious. People want meaningful activities, freedom to make their own choices, some extra cash, and to keep their minds sharp while connecting with others.

Look at Tom and Linda. He used to be an engineer but now spends hours in his workshop creating beautiful pieces from wood. She was running a school before retirement but discovered she loves putting together community events. Both realized they needed something more fulfilling than just playing golf or binging shows all day. So, they launched a small Etsy shop and part-time event consulting service - and they've never been happier.

You might be closer than you think to your own second-act success story.

 

Identifying the Right Business Idea for Your Second Act

You don't need the "next big thing." You need the right thing for you - something that aligns with your strengths, interests, and the lifestyle you want to lead in retirement.

After years - maybe decades - of professional experience, you've built up more skills, knowledge, and networks than most startup founders. That's your advantage. The key is choosing a business idea that plays to those strengths while honoring retirement's freedom and flexibility.

4 Questions to Ask Before You Start

Before jumping into any idea, take time to reflect on these core questions:

• What do I enjoy doing?

Think beyond what you're good at - what energizes you? What do you find yourself talking about or helping others with for free?

• What am I good at?

This could be technical knowledge, communication skills, creative talent, or decades of leadership experience. Don't discount your soft skills - they're often more valuable than you think.

• What problem can I solve?

The best businesses solve real problems. Is there a challenge you've faced that others still struggle with? Or a niche you understand deeply because you've lived it?

• What lifestyle do I want?

Do you want a few hours of meaningful work each week, or are you ready to build something bigger? Will you travel? Care for grandkids (Shari and I have nine grandkids, so we have quite a busy schedule)? Your business should fit your lifestyle—not the other way around.

 

10 Second-Act Business Ideas to Consider

Here are ten low-barrier, retirement-friendly business ideas that work well for encore entrepreneurs:

1. Consulting in Your Industry - Leverage your decades of experience to offer specialized insights, advice, or problem-solving to companies, startups, or nonprofits. Whether you work on short-term projects or retainers, consulting allows you to stay in your field without the full-time grind. Clients value your wisdom, network, and seasoned perspective.
2. Coaching or Mentoring - Help people grow in their work or personal lives by sharing what you've learned over the years. You could guide someone through a career change, help a new manager find their leadership style, show someone how to juggle life's demands better, or teach that special skill you've mastered. It's incredibly fulfilling to watch people transform with your guidance, and you'll build genuine connections that matter.
3. E-Commerce Store - Sell physical or handmade products you create—or curate—through platforms like Etsy, Shopify, or Amazon. Whether art, vintage items, hobby gear, or something custom, this path lets you run a business from home on your schedule. You can scale quickly and tap into global markets with minimal overhead.
4. Digital Products - Package your expertise into downloadable resources like checklists, guides, courses, or templates. Once created, digital products can be sold repeatedly without inventory, making this a highly scalable and passive income-friendly model. It is ideal for those who want to teach or share knowledge without direct client interaction.
5. Freelance Services - Offer remote services like writing, graphic design, virtual assistance, bookkeeping, or web development to clients worldwide. Freelancing gives you complete control over your hours, workload, and rates. It's a flexible, low-barrier way to earn from existing skills.
6. Event or Travel Planning - If you're the person everyone turns to when they need something organized, why not make it your business? You could help couples plan their perfect wedding day, bring families together for reunions, show visitors the hidden gems of your hometown, or create peaceful getaways for small groups.
7. Pet or Home Services - Offer in-demand services like dog walking, pet sitting, house watching, light repairs, or gardening in your local area. This kind of work keeps you active and engaged in your community and offers great flexibility. It's perfect for animal lovers or those who enjoy working with their hands.
8. Tutoring or Teaching - Share your subject-matter expertise or life skills by teaching others online or in person. There's a strong demand for skilled and patient instructors, from math tutoring to adult education or creative workshops. Platforms like Wyzant, Outschool, and Teachable make it easy to get started.
9. Local Tours or Experiences - Design and lead unique local experiences, from historical walking tours to cooking classes, birdwatching outings, or art walks. This is a fun way to meet new people, share your passions, and generate income through storytelling and hospitality. You can promote it through Airbnb Experiences or local tourism groups.
10. Nonprofit or Mission-Based Venture - If there's something you really care about, why not build an organization around it? You could start a nonprofit that tackles a problem you see in your neighborhood, raise awareness about an issue nobody's talking about, or gather donations for something that matters to you personally.

It's not about making money—it's about making a difference. And there's something powerful about creating something meaningful that could still be helping people long after you're gone.

You don't need a big budget or fancy tech to get started. You need an idea that feels like you.

 

How to Validate Your Business Idea Without Risking Your Nest Egg

Before investing your time, energy, or retirement savings into a business idea, it's smart to ensure it has legs. Fortunately, you don't need to write a business plan, build a website, or spend thousands to determine if your idea is worth pursuing.

Validation simply means confirming that real people are willing to pay for the solution you offer and that you're the right person to deliver it. Done right, this step can save you months of frustration and thousands of dollars.

Simple Validation Techniques

These simple, low-cost methods can help you test an idea before going all in:

• Use online tools to research demand.

Google Trends, Answer the Public, and even Amazon can help you gauge interest. Search for your topic and look for questions people ask, books they buy, or products they review. These are signs of active markets.

• Talk to potential customers.

It might feel awkward at first, but honest conversations are gold. Reach out to 5–10 people who fit your ideal customer profile. Ask open-ended questions like:

"What's your biggest frustration with [topic]?" or "How do you currently handle [problem]?" Listen more than you talk.

• Launch a mini-test or MVP.

An MVP (Minimum Viable Product) is a small-scale version of your offer. It could be:

A one-hour webinar

A simple Etsy listing

A free downloadable guide

A social media post gauging interest

The goal isn't to go viral. It's to see if people engage, ask questions, or take a small next step (like signing up or buying).

The 3-Step Retirepreneur Validation Framework

At Retirepreneur, we teach a simple but powerful validation method:

1. Problem – Is the problem real, painful, and specific? Avoid vague "nice-to-have" ideas. You want something that keeps people up at night or bugs them enough to pay for a solution.
2. Audience – Do you know exactly who has this problem? Retirees often succeed by focusing on niches they know - such as teachers, engineers, or small nonprofits. Specificity is better than broad.
3. Solution Fit – Does your idea solve that problem for that audience? Can you explain it in one sentence? If not, you may need to simplify or adjust your offer until it clicks.

You're on the right track when you hit all three - a real problem, a clear audience, and a strong solution fit.

During my entrepreneurial studies at the University of Florida, I consistently heard the following: If you "create insane value for customers" and "solve their problems", you are off to the right start!

 

Tools and Technology: What You Really Need (and What You Don't)

Technology can feel intimidating—but starting a business in retirement doesn't mean you have to become a tech wizard. You only need a few basic tools to run a simple, professional, and profitable business.

Many retirees overestimate what is required on the tech side. You can build a second-act business with just a laptop, an internet connection, and a handful of beginner-friendly tools. You don't need to be on every social media platform, learn to code, or hire a pricey web developer—unless you want to.

Must-Have Tools for Beginners

These are the essential tools we recommend to get started. Each one has a short learning curve and offers plenty of tutorials:

• Website Builder: Wix or Squarespace
• These platforms let you build a clean, professional website without coding. They offer drag-and-drop functionality, mobile responsiveness, and templates designed for small business owners.
• Pro tip: Start with a homepage and contact form - you can grow from there.
• Email Marketing: Beehiiv or MailerLite
• Want to stay in touch with customers or grow an audience? These email platforms are easy to use and free up to a certain number of subscribers. You can send newsletters, promotions, and automated follow-ups—all with simple drag-and-drop editors.
• Scheduling & Invoicing: Calendly and Wave / FreshBooks
• If you offer services (consulting, coaching, tutoring), Calendly lets people book appointments without back-and-forth emails.
• Wave is a free, beginner-friendly accounting tool for sending invoices, tracking expenses, and keeping records organized for tax time.

With just these three categories of tools, you can handle 80% of your digital business needs.

Retiree-Friendly Tech Tips

You don't need to do everything yourself. Here's how to stay efficient and sane:

• Know when to outsource.

Do you need tech support, graphic design, or website fixes? Sites like Fiverr and Upwork offer affordable freelance help. Focus on what you enjoy and outsource the rest.

• Stick with tools that match your goals.

Don't fall into the trap of "shiny object syndrome." Choose tools based on what your business needs, not what's trendy. You don't need a TikTok scheduler if you're not selling on TikTok.

• Use learning resources designed for beginners.

YouTube, Skillshare, and Coursera offer simple, low-cost tutorials for retirees starting businesses. Many tools also include built-in guides or free live training.

You're not too old for tech - you just need the right tools, pace, and support.

 

Legal & Financial Foundations for Retiree Entrepreneurs

Starting a business in retirement is exciting - but before you dive in, it's essential to get your legal and financial ducks in a row. The proper structure and thoughtful planning can protect your assets, simplify taxes, and help you avoid unexpected impacts on Social Security or Medicare benefits.

The good news? This doesn't need to be overwhelming. With a few simple steps—and a little professional guidance when needed - you can build your business on a strong, secure foundation.

Business Structure & Registration Basics

One of the first decisions you'll make is how to structure your business legally. Most retiree-run companies fall into one of two categories:

• Sole Proprietor

This is the simplest option. No formal registration is required (aside from any local licenses), and you report income and expenses on your personal tax return.

Pros: Easy setup, no separate business tax filing.

Cons: No personal liability protection - your personal assets are at risk if the business is sued or goes into debt.

• Limited Liability Company (LLC)

An LLC separates your personal and business finances, offering liability protection. It's ideal if you're dealing with clients, signing contracts, or selling products.

Pros: Protects your assets, looks more professional, and allows pass-through taxation.

Cons: Depending on your state, it requires a small annual fee and paperwork.

Westmont Group LLC, owner of Retirepreneur, is set up as an LLC, and we have engaged legal counsel to draft a comprehensive Operating Agreement to protect our personal assets further.

Most states make registration easy through their Secretary of State website. Online services like LegalZoom can also walk you through it.

Remember to check if your local area requires a business license or permit - even for home-based businesses.

 

Financial & Tax Considerations

Your new income stream might affect more than just your wallet - it could also impact your retirement benefits.

• Social Security

Business income could temporarily reduce your monthly benefits if you're under full retirement age. Once you reach full retirement age, there's no penalty, no matter how much you earn.

• Medicare Premiums

Earning more may increase your monthly Medicare premiums. Known as IRMAA (Income-Related Monthly Adjustment Amount), these adjustments are based on your income from two years prior.

• Separate Business Finances

Open a separate bank account and use accounting software (like Wave or QuickBooks) to track income and expenses. This will keep your finances clean and make tax time much easier.

• When to Consult a CPA or Attorney

If you're unsure how your business might affect your taxes or retirement benefits - or if you're taking on legal risk—it's wise to spend a little for peace of mind. A CPA or small-business attorney can help you structure things correctly.

With the proper setup, your second-act business can be rewarding and responsible - without threatening your financial future.

Let me add this - I am a CPA with extensive small business background, and I hired a tax CPA, a retiree CFP specialist and legal counsel.  Hiring experts is a small price to pay, considering the benefits of their services. 

 

Finding Your First Customers Without Feeling Like a Salesperson

For many retiree entrepreneurs, "selling" feels awkward or pushy. But here's the truth: you don't need to become a slick marketer to attract clients. Your best tool is one you already have - your existing relationships and reputation.

By leaning on your experience, connections, and a few smart visibility tactics, you can start finding customers in a way that feels authentic - not salesy.

Start with Your Existing Network

You've built trust over a lifetime of work. Now it's time to let people know what you're doing—and how you can help.

• Send a warm outreach email.

Keep it casual. Start with a personal update, share your new venture, and invite people to keep you in mind or pass your info along. Example:

Hi [First Name], I hope you're doing well! I wanted to share something exciting—I've launched a part-time [coaching/consulting/service] business focused on helping [target audience] with [the problem you solve]. If you know anyone who could use support in this area, I'd appreciate it if you passed my name along. Thanks so much!

• Leverage LinkedIn and community groups.

Update your profile with your new business. Then, join conversations in LinkedIn groups or local Facebook communities. Don't pitch - participate. When people see your thoughtful responses, they'll check out your profile and learn what you do.

Quick Win Strategies

These simple tactics can help you attract your first few clients with minimal cost or tech skills:

• Offer a referral program.

Give friends or past colleagues a small thank-you (gift card, discount, or free session) for referring someone who becomes a client.

• Do local outreach.

Introduce yourself at local meetups, libraries, business groups, or community centers. If you're offering a service people need - like tutoring, tech help, or small business consulting - these spaces can be gold mines.

• List yourself on service directories.

Websites like Thumbtack, Alignable, and Bark make it easy to promote your business locally or online without building a huge online presence.

• Gather testimonials early.

Even a free or discounted first client can give you a powerful quote. Testimonials build trust, and trust builds momentum.

• Encourage word of mouth.

Make your business easy to describe in one sentence so people can confidently refer you. "She helps retirees get their finances in order" is far more shareable than "She offers financial wellness packages for pre-retirees."

You don't need a huge following to attract your first few customers - you need to be visible, clear, and confident in what you offer.

 

Success Stories from Real Retirepreneurs

Starting something new later in life can feel scary - but you're not alone. Thousands of retirees have already done it, with no business experience. Their stories prove that second-act success is possible with the right mindset and a clear plan.

Here are a few real-life examples to inspire your journey:

Meet Dennis: From Engineer to Consultant

After retiring from a 35-year career in manufacturing, Dennis wasn't ready to stop working entirely. He'd spent decades solving operational problems - and realized small manufacturers could benefit from that expertise.

He launched a simple consulting business from home, using LinkedIn and a few industry contacts to land his first clients. Dennis meets virtually, keeps his schedule part-time, and is charged by the project.

What worked: Tapping into his existing network and keeping things simple - no office, no employees, just his know-how.

What he'd do differently: "I would've started with a niche focus instead of trying to help everyone at once."

Meet Sharon: Crafting Joy Through Her Etsy Shop

Sharon always loved crafting - quilts, cards, and homemade gifts. When friends asked to buy her creations, her daughter helped her open an Etsy store.

She started with just 10 listings and learned as she went. Orders trickled in at first, then picked up after she added better product photos and started sharing her story on social media.

What worked: Leaning into her passion and asking her family to help with the tech side.

What she'd do differently: "I waited too long to treat it like a real business. Once I did, things took off."

Meet Mike: Starting a Local Handyman Service

Mike spent his career in construction. After retirement, he wanted something flexible that would still allow him to stay active. With a few flyers, a Facebook post, and word of mouth, he launched a local handyman business doing small jobs - furniture assembly, gutter cleaning, and light carpentry.

He works just three days a week and loves chatting with clients. His wife jokes he's busier now than when he worked full time.

What worked: Keeping overhead low and starting hyper-local.

What he'd do differently: "I wish I'd gotten business insurance sooner - it gave me peace of mind."

Curt Tip: TAKE ACTION… any action is better than talking or planning endlessly!

These stories aren't fairy tales—they're practical examples of retirees using their skills, interests, and connections to build something meaningful. You can do the same.

 

Final Thoughts: Encouragement, Confidence, and Your Next Step

Look at everything you've already done - built a career, run a household, raised kids, weathered life's storms, and made thousands of tough calls along the way. When you think about it that way, starting a small business in this new chapter? It's just another adventure on your journey.

And remember—you don't need to do this by yourself, and you don’t need to have it all figured out tomorrow. Take it one step at a time.

Let's recap the simple roadmap to get started:

• Choose the right idea that fits your skills, lifestyle, and values - not what's trendy.
• Validate it quickly with real-world feedback before investing money or time.
• Set up basic tools and systems that match your goals and comfort level.
• Take care of legal and financial basics so your business protects, not disrupts, your retirement plans.
• Find your first customers by leaning into your network and doing what already comes naturally - building trust.

If you're feeling a spark of motivation, follow it. You don't need to have everything figured out today. Just take the next right step.

You've still got plenty of chapters left to write. Why not make this one your most meaningful yet?

Related Posts:

Business Ideas for Retirees

Validate Business Idea

Retirement Business Plan

Legal Considerations Retirement Business

How to Get First Customers