Getting started as an entrepreneur can be a scary process. When you’re accustomed to having a reliable paycheck from a company, the idea of creating your own income can be hard. But if you have the dream of entrepreneurship, it can be a hard one to shake.

Starting a business often becomes a second career after working as an employee. A desire to set their own schedule, reap the benefits of the business’s profits, and build something from the ground up are just some reasons people cite for transitioning into entrepreneurship. But it isn’t easy, and there are some basic characteristics you need to have to make it a successful journey.

In today’s episode of Creating Your Encore Career, Chris Lalomia, owner of The Trusted Toolbox in Atlanta, Georgia, joins Lynn to talk about how he made the leap from a career in mechanical engineering to founding his successful handyman company. At 37 years old, he couldn’t ignore his dream of owning a business any longer. It coincided with the recession of 2008, but he persevered, his company survived, and today, he has 40 employees in the metro Atlanta market.

Chris Lalomia is still learning business lessons 14 years into his second career, and he shares some of his insights with Lynn.

We'll dive deeper into these concepts:

Chris Lalomia’s background in engineering and banking, why he started his business, The Trusted Toolbox, and what his company looks like today
The roadblocks he faced as he shifted into entrepreneurship and how his business plan helped keep him on track
How Chris decided what he needed help with as he developed his business and how he prioritizes his time
Why culture plays a role in how he runs his company and the feedback he receives from other entrepreneurs
How timing and the effort you’re willing to put forth affect your business
The reason you’re selling yourself to your customers as much as you are your product
The three things you need to become a successful entrepreneur
What The Trusted Toolbox has in its future
Chris’s advice for those seeking an encore or second career

Now, for some action steps:

Download the free worksheet: Three Steps You Need for a More Productive Workday
Visit Chris Lalomia’s website: https://thetrustedtoolbox.com
Listen to the podcast: The Small Business Safari
Get the book: From the Zoo to the Wild: Your Guide to Entrepreneurial Freedom and Wealth
Visit Chris’s LinkedIn page: linkedin.com/in/chrislalomia

My Resources:

A quick guide to help you get started on your Encore Journey

encorecareermindset.com

My Website

https://www.lynnfriesth.com/

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If you enjoyed this episode, we've created a PDF that has all of the key information for you from the episode. Just go to the episode page at https://www.lynnfriesth.com/podcast1 to download it.

I thank you so much for being here and I’ll see ya next time on Creating Your Encore Career.

— Lynn

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Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com.

Episode 13843: LOCKED IN - 7-2-25