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The Midlife Entrepreneur’s Playbook: Essential Tips for Starting Over

Midlife is the perfect time to start fresh – why not build a business that works for you? Get midlife entrepreneurs practical tips to launch with confidence and minimize risk.
The Midlife Entrepreneur’s Playbook: Essential Tips for Starting Over - Guidant Financial Blog

Midlife isn’t about crisis. Today, midlife has a new meaning: a time to restart and reinvent yourself. There’s even a name for it – midlife entrepreneurship – and it’s gaining momentum.

This stage of life brings big changes. According to Psychology Today, it’s a time of change in many aspects of your life. Shifts in relationships, health, and personal priorities. But what about your career?

If you’ve been dreaming of doing something different, why not take this opportunity to build a business that truly aligns with who you are now – and where you want to go next?

Most midlife entrepreneurs have spent decades in the corporate world or at least in different job markets. In midlife, you can leverage that experience and your professional networks to start a new business that puts you in control of your time, income, and future.

In this guide, we’ll walk you through the biggest challenges – like managing finances, keeping up with new tech, and finding that sweet spot between work and life. Whether you’re chasing a lifelong passion or just ready for something new, you’ll get real, practical advice to help you make it happen. Don’t forget: You already have experience and strengths to build on.

We’ll show you how to minimize risks, play to your strengths, and create a business that fits your life – whether that means more flexibility, more freedom, or just more time for what matters most.

1. Consider Your New Goals

Before you begin your new business, whether it’s a wine bar or an accounting firm, take a long walk and think about your goals. Your goals today are likely different from when you were young and searching for your first or second job. It’s also likely they’ll be different from your goals once you retire. These midlife goals may include a few ideas like these:

  • Finding meaning and purpose.
  • Work flexibility.
  • Choosing a totally different, new industry.
  • Taking a risk.
  • Being your own boss.
  • Finding time for hobbies or fitness.
  • Traveling off-season.
  • Taking care of your health.

If you don’t have a business idea yet, don’t worry. Instead, spend a little time thinking about the different industries you’ve worked in and the myriad skills you’ve accrued over the years. If you’ve always wondered about a certain industry, include that on a list of potential businesses.

As you can see, these goals for entrepreneurial success are a mix of personal and professional, but they often align. For example, finding purpose could mean starting the new business you’ve always dreamt of but been afraid of doing — a decision that affects your personal life, too.

Discover the perfect niche for your business – follow these 3 simple steps to find your fit.

2. Set Your Business Up for Success – From Day One to Your Exit

An older couple smiling while holding pencils and planning at their desk. The Midlife Entrepreneur’s Playbook: Essential Tips for Starting Over - Guidant Blog.

Now that you’re serious about starting a business, it’s time to map out the details.

Start with the basics – like securing the right licenses and putting together a solid business plan. If you need funding, there are plenty of options, from traditional bank loans to SBA loans. But one method is gaining popularity, especially for those who want to avoid taking on debt: 401(k) business financing, also known as Rollovers for Business Startups (ROBS). This allows you to use retirement funds to start or buy a business – without loans, interest, or monthly payments. Companies that specialize in small business financing, like Guidant Financial, can help you explore if it’s the right fit.

And while you’re planning how to launch your business, think about how you’ll eventually step away from it, too. Will you build it up to sell? Pass it down to family? Or run it until you’re ready to retire? Having an exit strategy now – whether it’s years down the road or sooner – gives you more control over your future.

Find the best way to fund your business – explore the top 7 small business financing options today!

3. Use Your Powers of Delegation

When Jay Newton-Small started her business midlife, MemoryWell, she faced a steep learning curve. Coming from a journalism background, she knew storytelling inside and out – but business plans, sales, and marketing were unfamiliar territory. What she did know? Fundraising. So, she leaned into that strength and found support for the rest. Today, MemoryWell has grown into a national network of over 400 professional writers, partnering with numerous assisted living facilities to improve care through storytelling.

No one is great at everything, and you don’t have to be. Maybe you have a knack for marketing but need help with accounting, or you’re confident in operations but unsure about sales. The good news is, you can delegate. Whether it’s hiring employees, bringing in contractors, or outsourcing specific tasks, there are plenty of ways to fill the gaps – so you can focus on what you do best.

4. Find a Mentor

A younger and older man collaborating together and smiling. The Midlife Entrepreneur’s Playbook: Essential Tips for Starting Over - Guidant Blog.

Starting a business in a new industry? A mentor can be a game-changer. And at this stage in life, having one who’s younger than you can be just as valuable as having one with years of experience. Younger mentors often bring fresh perspectives and a strong grasp of new trends and technology – areas that can make a big difference in your business.

If technology isn’t your strong suit, tap into your network. Talk to people who are in the know, ask questions, and figure out where you should focus your learning. With AI and other innovations shaping the business world, staying informed is more important than ever. Whether it’s reading up on the latest trends, taking a course, or connecting with experts, keeping up with technology isn’t just helpful – it’s key to your success.

You don’t need experience to succeed – follow these 5 steps to start a business in a brand-new industry.

5. Be Smart About Financial Risk

Starting a business always involves risk, but the stakes feel different in midlife. Just like with investing, the closer you get to retirement, the less time you have to recover from big financial setbacks. That’s why it’s important to be strategic about how you fund your business.

The good news? There are plenty of options that don’t require taking on massive debt. 401(k) business financing, also known as Rollovers for Business Startups (ROBS), lets you use retirement funds to start a business without loans or interest. Small Business Administration (SBA) loans typically offer lower interest rates and longer repayment terms. Portfolio loans let you borrow against investments without selling them. The key is finding a financing method that works for you – so you can build your business with confidence and financial security.

Learn how to use your retirement funds to start a business debt-free with 401(k) business financing, also known as Rollovers for Business Startups (ROBS) here’s everything you need to know.

6. Don’t Skip ‘Me Time’

Running a business takes energy, and so does everything else in midlife – family, relationships, health, and daily responsibilities. With so much on your plate, it’s easy to put yourself last. But if you’re always running on empty, everything else suffers too.

‘Me time’ isn’t just a luxury. It’s a necessity. Whether it’s taking a walk, hitting the gym, reading a book, or just sitting quietly with a cup of coffee, recharging helps you show up better in every part of your life. Your business, your family, and most importantly, you will benefit when you make time to reset.

Moving Forward in Midlife

Smiling business owner outside of a storefront with an "open" sign. The Midlife Entrepreneur’s Playbook: Essential Tips for Starting Over - Guidant Blog.

Midlife is full of change, but it’s also full of opportunity. Starting a business at this stage comes with its own challenges, but with the right approach – setting clear goals, managing risk wisely, leaning on mentors, delegating, and making time for yourself – you can build the life and career of your dreams.

You’ve got experience, skills, and a vision for what’s next. Now it’s time to make it happen. Here’s to your next chapter in business and in life!

Turn your skills and passions into a successful business – follow these 7 steps to find the right fit for you.

Get the Right Support for Your Next Chapter

Starting a business is a big step, but you don’t have to do it alone. Guidant Financial has helped over 30,000 entrepreneurs – many in midlife – turn their business dreams into reality.

From 401(k) business financing (ROBS)  a debt-free way to fund your business – to SBA loans and expert guidance, we make it easier to get the funding and support you need. Whether you’re just getting started or ready to take the next step, we’re here to help.

Ready to make your business happen? Pre-qualify with Guidant today.


“When Falling Sky Brewing presented itself as a great opportunity for me, I needed the capital. Traditional lenders weren’t going to do it. I took a chance on myself that I could grow my business and my 401(k)… And I thought, ‘You know what? I could do this without overhanging debt.‘”

Stephen Such, Falling Sky Brewing

Read the stories of REAL small business owners who work with Guidant.

Want to Use ROBS to Start a Business?

Our step-by-step Guide to Rollovers for Business Startups is a complete handbook of everything you need to know about using ROBS to start or buy a small business or franchise.

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