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Freelance After 50 Newsletter

F50 Issue #10: How to Reinvent Yourself with a Second Act Career

Published 3 months ago • 5 min read

F50 Issue #10: November 21, 2023


How to Reinvent Yourself with a Second-Act Career

In a recent Longevity Gains podcast episode, Brian Clark interviewed Michael Clinton, former president/publisher of Hearst Magazines, author of the book ROAR into the second half of your life, and founder of the ROAR forward membership and business intelligence platform for people aged 50+.

Clinton is a great example of someone who began a vibrant second career when he became an author at the age of 70. He lives a full life, remains physically active, and encourages others to reimagine their futures, refusing to let age hold them back.

We have many people in our Freelance University community who inspire us with their courage and determination as they dive into the world of entrepreneurship and reinvent themselves.

This time, we’ll meet Kevin Kroeker, who started a freelance business in his 50s after a fulfilling career as a health care aide. He wasn’t ready to retire but needed work that was less physically demanding.

We interviewed him about his experience setting up a business and adjusting to working from home.

Tell us a bit about yourself. What did you do in your previous career, and how did you get into freelancing?

Kevin: I was a health care aide in nursing homes. I cared for residents with dementia, MS, ALS, and Parkinson’s disease. I thoroughly enjoyed caring for the needs of all my residents and getting to know them (their life history) and their families.

I also enjoyed working as a team with other health care aides and nurses on each floor. A daughter of one of my residents once said, “It takes a village.” And she was absolutely right! It was both a challenging and rewarding career.

I got into freelancing after some health challenges dictated that I could no longer do such a physically demanding job. My wife was already working as a freelancer with VAClassroom (and then Freelance University), so I started checking out what kind of courses were available and decided which ones I was interested in taking.

What appealed to you about the idea of freelancing?

Kevin: The biggest appeal was that I can dictate the hours that I take courses to upgrade my skills or work on a project for a client. As a care aide I was up at 6:00 am and worked from 7:00 am to 3:00 pm.

As a freelancer I typically get up around 10-ish, and my commute to work is to walk to the kitchen to get my granola for breakfast and then walk to my home office. I do often work for a bit in the evening, but that’s my choice!

How did you decide on a niche?

Kevin: I tried a number of courses and narrowed it down to what I enjoyed doing. Then I took courses to add to areas where I needed additional skills.

My niche right now involves helping small businesses build a strong online presence with the services I provide — Local Search Engine Optimization (SEO) services (including Google Business Profile), podcast production and editing, and remote bookkeeping.

I discovered these services suited my analytical mind.

What challenges have you faced while building your business?

Kevin: Marketing myself is still one of my biggest challenges. LinkedIn and Instagram are my primary social media channels. I post and network on Linkedin on a fairly consistent basis, and have found that extremely effective. It’s helped me connect with potential clients and build a good reputation.

Also, getting my website to where I want it has been a bit of an adventure, but I’ve got it where it needs to be and lets people know exactly what services I provide.

What resources have been most helpful to you while building your business?

Kevin: I’ve got a few favorites that were recommended to me and that I discovered from networking on LinkedIn.

What tools and apps have been most helpful?

Kevin: I would start with a free trial to try out different tools, and if I heard a lot of good reviews from other people, then that was a good sign. For instance, I had heard many positive reviews about HoneyBook and was incredibly impressed with how effective it was when I took it for a spin.

The main tools I use with my business are:

What have you learned about yourself since embarking on your freelance journey?

Kevin: I’ve learned that I’m a very resilient person who is like a dog with a bone when trying to figure out why something isn’t working properly. This comes in handy when you're working on your own website and it’s being temperamental.

I also have great attention to detail, which is very helpful with bookkeeping. I also enjoy learning new things to upgrade my skills, and there have been many courses I needed to take to be able to provide bookkeeping services. I am now certified as a QuickBooks Online ProAdvisor.

I always thought of myself as a shy person and was surprised to discover how comfortable I am networking online. I’m less comfortable networking at in-person events, so it’s nice to have the online option as well.

What advice do you have for 50+ people wanting to start a freelance business after working in other careers?

Kevin: If you enjoyed your career, then first look at what remote career paths are similar to the work you did. Take advantage of the experience you have from whatever work you did.

Don’t start from scratch; instead use that experience as a stepping stone. The work experience you already have will be invaluable to whatever you choose to do in your freelance business.


Work from Home Wisdom

Kevin shared these tips that have helped him be productive and efficient while working from home:

  • Try to have a set schedule each day and take a brief break every 30 minutes or so.
  • Check your emails only 2 to 3 times a day so that you’re not constantly distracted by replying to messages.
  • Block off times to do major projects such as writing blog posts, recording a podcast, or finishing client work.

Insider Resources

For more inspiration, check out the book ROAR into the second half of your life by Michael Clinton. It will help you reimagine and embrace your future through the ROAR process:

  • Reimagine yourself.
  • Own who you are.
  • Act on what’s next.
  • Reassess your relationships.

And if you’re feeling overwhelmed, take a deep breath and be inspired by this quote from Mark Twain:

“The secret of getting ahead is getting started.”

Here’s to taking the first step to reimagining your own second-act career!

Until next time,

Craig & Kelly

PS. If you are interested in freelancing, but not sure how to get started, then join our FREE Masterclass, Discover a 4-step Framework to Start Freelancing the Right Way!

Co-founders of Freelance University

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Freelance After 50 Newsletter

Craig & Kelly Cannings, Co-founders of Freelance University

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