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Embracing a Career Change as a Second-Act Entrepreneur

By Judi Jacobs November 08, 2021 Managing Money

These days it is not uncommon to make a career change mid-life. Many people in their 50s – and even into their 60s – are asking themselves, “What do I want to be when I grow up?”

The numbers of those 60+ having to continue to work later in life are growing due to both need and desire. Many are drastically changing course, realizing that remaining in the workforce for another 20 years opens an opportunity to follow a passion.

More than ever baby boomers are starting businesses of their own. There is even a term for it, ‘boomerpreneurs.’

I am a perfect example of this phenomenon. I am a lawyer by trade, I loved practicing law and was very fortunate to have had a successful law practice. However, when I had four teenagers at once, I was forced to pause my legal career to be home.

I realized over the years that my passion was technology and teaching others about technology. As all my kids were off to college and beyond, I began casually helping others. I decided this was how I wanted to spend my work days, and so I started The Tech Wizard.

Taking Advantage of Technology

Fortunately, in this day and age, there are many aspects to starting a business that no longer require a substantial financial undertaking.

Technology can allow you to have opportunities that existed never before. Almost every element of running a business can be underwritten with less capital providing the infrastructure necessary to launch operations and generate income.

While this is a great benefit to many ‘boomerpreneurs,’ it can also be a roadblock for those who don’t feel comfortable with technology and aren’t fluent with computers, social media and apps.

I was lucky because technology is my thing. Using tech tools to get my business started came naturally to me. Yet, there was still a process of discovering what apps or services were best for me and my style of work.

For many, the technological options can be overwhelming. I work with ‘second career’ entrepreneurs and small business owners all the time: to provide them guidance, to help set up their business or change systems as needs evolve.

Here is a list of some of the apps and software that I recommend to my clients who are considering launching a small business. These systems can help your business run more efficiently and reduce your stress level significantly, without costing an arm and a leg.

Financial Management


Harvest is a simple time tracking tool, which allows you to track time and expenses. It also makes it easy to create and send professional looking invoices.

Stripe and PayPal

Great options to accept payments via credit card are Stripe and PayPal. Free to set-up and get started, each costs a flat percentage of charges (usually around 3%). Even better, they are mobile friendly. Payment can be collect in-person using a smartphone or terminal, or online.

Quickbooks and Freshbooks

Quickbooks and Freshbooks both offer accounting software to help you track your income, expenses and generate invoices to keep the book balanced. You can also opt to collect payments (for a fee) and more. Both apps integrate with Stripe and PayPal for easy tracking of expenses and income.

These software systems interactively function behind the scenes. Once set up, they act as your virtual CFO.


These days, a website is an essential part of doing business, and for most business, this is a must! Fortunately, there are many do-it-yourself website build options out there, such as Weebly and Wix. For an e-commerce site, Shopify provides an accessible platform to set-up an online store.

These platforms can get you up and running with an online presence in a short amount of time and with little technical knowledge. What’s more, their support staff is very well-versed and helpful if you hit any snags along the way – or need customization to support your website needs.

For the more advanced user, WordPress is a fantastic platform that can help you create a custom website without having to learn how to code. There are numerous tutorials and online help guides to help you through the process if you want to do it all yourself.

Social media has completely changed the world when it comes to marketing. Options to help reach a target audience, including Facebook, Twitter, Pinterest and LinkedIn, provide a competitive presence at a fraction of the cost of traditional marketing.

There is no doubt a learning curve to using, connecting with and engaging your audience via social media. Fortunately, there are a plethora of articles, videos and classes (online and in-person) that can get you up to speed on how to most efficiently use it for your business.

Human Resources

No one can do it alone. These days, you don’t need to hire full-time team members and provide them an office space.

There are ‘virtual assistant’ options who bill by the hour. You can hire someone for 5, 10 or 20 hours a week, so you are only paying for what you need. I am based out of Los Angeles and have a virtual assistant who lives in Iowa.

With Dropbox, Asana, 1Password, email, Slack and video conferencing we can communicate and share documents seamlessly, so that the time difference and 1,800-mile distance isn’t an issue.

Virtual assistants do almost every type of task integral to your particular business. You can pick and choose from the management of social media, photography, video editing, logo design, building a website, answering phones and email, booking travel and more.

Taking the Plunge: It’s a Mindset Thing

The nugget when considering whether to start a new business or redefine how you are currently conducting business is: do what makes you happy. But you have to believe in you.

As the saying goes, “Do what you love, and you’ll never work another day in your life.” Being able to wake up and follow your passion every day will keep you healthy, vibrant and alive.

Being an entrepreneur is a lot of hard work and can be lonely, but I wouldn’t have it any other way. Surround yourself with people that support your goals and desires. Get rid of negative vibes and self-talk. Just do it. I am grateful for every day and have never looked back.

Have you considered a second-act career as an entrepreneur? What is holding you back from taking the plunge? Please share your concerns and thoughts below!

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The Author

Judi Jacobs is a lawyer-turned-tech nerd and the founder of The Tech Wizard. As a tech coach and consultant, Judi works with adults 50+ and small businesses to help make technology more user-friendly through small group classes and one-on-one training. Learn more at

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