The Adventure Of Starting A Small Business: 4 Tips From Someone Who Has Lived It

Judy Castleberry is the director of the San Juan College Enterprise Center, and she has a wealth of experience in self-employment and small business. In the blog below, she describes the opportunities and challenges that come with working for yourself; and she offers some practical tips to help you thrive in self-employment. We’ve included some bonus tips of our own as well

When I was almost 50 years old, a friend and I held hands and jumped off a cliff together. No, we didn’t think we were Thelma and Louise and it wasn’t a physical cliff. But the cliff we jumped from was, metaphorically speaking, just as daunting as that cliff. Our cliff was starting a small business.

Scared? Of course, we were! We were two women at the latter end of middle age quitting our careers to strike out on our own without an employer behind us. Pam, my friend, and business partner was married to a wonderful, supportive man; I was a single parent with all the responsibilities of supporting my family on my shoulders. But we weighed the odds, decided we were ready for the new adventure, and jumped off the cliff.

Ten years later, we sold our senior care business, which had grown to 60 employees. It was time for the next adventure. We walked away not only with a nice check for our years of hard work but also with many lessons learned. What were these lessons and how do they apply to other folks starting a business in the second half of life?

1) Own What You Know

Pam and I had both worked since we were teenagers. I had gone to college and had worked as a social worker and long term care administrator. Pam had excelled in office skills and become a paralegal. Over the years we had developed many skills that worked to build the small business. I knew senior care and Pam could manage any office. The skills we had built over a lifetime of work helped shape the kind of business we wanted to start. It also gave us confidence in our own decision-making process when we needed to make critical decisions about the business.

2) Admit What You Don’t Know

Because we had 30+ years in the workforce, it was sometimes hard to admit we didn’t know everything. But it soon became clear there were things we needed to learn. For example, we were familiar with payroll and accounting, but neither of us had ever really been the “bookkeeper.” We had to admit that we needed help not only setting up our books but also using a bookkeeping system.

3) Find Your Resources

Once you admit what you don’t know, then it’s easier to go looking for resources. We became part of a business incubator, went to every training and workshop we could find and made friends with our CPA. Because our business was employee-based we also joined the local HR association. Building on what we already knew by adding to our skill set helped grow the business. Check into your own local resources.

Bonus tip: Make fintech your friend

Financial technology (“fintech”) tools and resources available for self-employed workers – whether contractors, freelancers, gig workers, or small business owners – are designed to make business operations a snap. AARP Foundation Self-Saver helps you manage bookkeeping and self-employment taxes like a pro (and without years of accounting, tax or bookkeeping experience!). From tracking your self-employment income and expenses to automatically preparing and filing quarterly taxes, Self-Saver lets you spend more time focusing on your business, and less time worrying about paying your taxes.

4) Network, Network, Network

One of the added bonuses of being established in careers and community was that we already knew a lot of people. In addition to building on what we knew, we built on who we knew. We talked to everyone we knew about our business — looking for clients and for resources, employees and community. One excellent piece of advice we received at the start was that when you are sick of talking about your own small business, you are just starting to breakthrough. I would also say that when people stop you at the grocery store to ask about your business, you are on the road. Network everywhere!

That cliff is a lot less frightening when you have a partner and know how to make a soft landing. May your landing also be a good one!

When it comes to starting your own business, challenges like the one that Judy experienced are more common than you think. The good news? You’re not alone! AARP Foundation’s tools and resources — such as Self-Saver and Work for Yourself@50+— are designed to help you launch your business and tackle self-employment with confidence.

Are you a Self-Saver user who has recently started your own business? Do you have tips you’d like to share? We want to hear from you. Send a note to Susan@self-saver.org and tell us about your experience for a chance to be featured on our blog.