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Career Transition

Are You Ready to be an Olderpreneur?

A few months ago, Prime readers were introduced to the topic of Olderpreneurs, older entrepreneurs over the age of 50 who choose to work for themselves or start new businesses later in their careers, rather than stay in their current jobs or retire completely.

This article discusses some next steps for those older entrepreneurs interested in exploring that direction.

Considering joining the growing ranks of Olderpreneurs?

Maybe it’s time to fulfill a lifelong dream and you could use some practical business advice. On the other hand, maybe you want to make a 180 degree switch from the type of career you’ve always had, but you’re not sure of much else beyond that. No problem—there are resources available to help with wherever you are along the path.

In 2012, the Small Business Administration (SBA) and AARP joined forces to specifically address the developing needs of this group, which they refer to as “encore entrepreneurs.” Their programs include counseling, training, and mentoring on various topics around starting or growing a business later in life, building on the knowledge, experience and skills that their clients already possess. To date, this partnership has successfully educated over 300,000 business owners around the country. Find more information here or contact your local SBA or SCORE chapter.

This wide range of information certainly checks the boxes in preparing us for what our heads tell us we need to know. But among the many benefits of midlife is that most women also start honoring what our guts tell us. Maybe you’ve dotted every “i” and crossed every “t” from the practical side, but you’re still not sure if you’re ready to make the leap. What else should you consider? What does it really take to be successful? For answers to these types of questions I contacted an expert, Dallas-based consultant Peggy Pepper. In addition to creating more than one successful business herself, she is a mentor and strategist for countless women entrepreneurs around the globe.

Her approach is comprehensive, uncovering a person’s inherent strengths through a series of assessments such as the DiSC and Clifton Strengths Finder, then considering how those can be translated to maximize one’s potential, both professionally and personally. The result is a custom Strategic Life Plan. Her clients are often “highly accomplished women, at the top of their game, who are longing for a new game…and want to self-express their gifts in the best possible way.”

According to Pepper, the following traits are commonly found among successful older entrepreneurs:

  1. First and foremost, the drive to be your own boss: Those who succeed are born with “you aren’t the boss of me” in their DNA.
  2. Passion of purpose: Does your passion keep you up all night to ‘get it right’? Passion will hone your focus and keep your mission on the front burner of your life.
  3. A thick skin: Every business experiences setbacks. Choose to see failures as course corrections…simply “more information” about what not to do or who not to do it with, Pepper recommends. She adds “See failure as a bruise, not a tattoo.”
  4. The ability to ask for help followed by acknowledgement of those who have: Acknowledgement creates momentum. It’s human nature. Others WANT you to succeed when they feel appreciated.
  5. A set of achievable goals: With regular check-ins for progress and dealing with setbacks. She advises charting your wins weekly and sharing them to keep momentum high.

Before making the leap, Pepper also suggests taking time to thoughtfully work through the following questions:

  • How honestly self-aware am I? What level of risk can I tolerate and embrace?
  • Besides myself, who can I count on? 
  • How much have I researched the need for my product or service?
  • How much money will this take? Where is it coming from?
  • How will I measure my successes and setbacks?
  • How will I deal with fear of success and/or fear of failure?

Regardless of a person’s background, prior experience, or industry, establishing and building the right support system, both professionally and personally, is crucial for every entrepreneur. Just as you will intentionally choose a name or logo design for your company, make time to intentionally develop your network of support as well. Starting your business with a foundation of wisdom, passion and the right team of advisors will go a long way in helping it succeed.

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