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5 Tips For Successfully Starting Your Career 2.0 At 50

4 min read

Do you feel like you’re not moving in the direction you want anymore? Maybe it’s time to decide the outcome of the next chapter of your life. By reimagining your personal goals you will be able to change your job, create your Career 2.0 and finally take a deep dive into owning your own business.

From the moment we first enter elementary school, we begin the process of routinely starting over. Just when we’ve got the hang of it, we find ourselves starring, as the newbies in middle school. A few short years later, there we are on the low end of the totem pole as high school freshmen. And as soon as we’ve risen to the top of that hierarchy as ruling seniors, we matriculate to college, repeating the entire process, only to be thrown right back to the starting line when we officially begin “adulting” as career professionals. 

In midlife, one would think that all of the starts and restarts we have successfully navigated since we were age six would reassure us that launching Career 2.0 should be a piece of cake. And yet self-doubt often rears its ugly head at the thought of beginning anew. 

Here are five tips for easing into Career 2.0 — otherwise known as following your passion — with confidence

 #1: Confirm that you have successfully overcome obstacles and new ventures in the past 

All those school years riddled with new beginnings should count for something! Take time to look at graduation photos, diplomas you’ve earned, offer letters, and other professional accolades you have collected over the years. Showing yourself historical evidence of past successes reinforces that you can certainly do it again (this time minus the angst of acne and which crowd to sit with at lunch).

 #2: Think through why you were successful in the past

Identify which tactics and strategies worked for you each time you found yourself at a new starting line. How can you apply those tactics and strategies to your new career path?

 #3 Find your new tribe

You may not be the first person to have had a stellar career in finance who now wants to reinvent yourself as an artist. Seek out other artists who have transitioned from non-creative industries. Google and other search engines, as well as word-of-mouth, can be your friend in identifying Meet-Ups and professional organizations where you can connect with your new tribe. As midlife women, it’s often hard to make new friends. The commonality of a shared interest or passion can help. 

 #4 Don’t be afraid to ask for help, even if you have to pay for it

There is no reason to board a Struggle Bus if you don’t have to. Chances are someone has already successfully accomplished whatever it is you are attempting to do. Seek them out, and don’t shy away from asking the questions that keep you up at night

SEE ALSO:  How To Survive The Wedding Season When You're Over 40 And Single

We don’t earn brownie points by figuring out our new careers by ourselves. And at this stage in life, why suffer through the hassle? If you don’t have personal connections in your new world, seek out professionals who can help you cut through the unknown, drama-free. Consultants and freelancers whose strengths are doing what you hate to do (and in half the time) are worth the investment. Check out Upwork,, or even Fiverr. Give them a small test assignment to ensure you work well together. 

 #5 Celebrate even the smallest of wins! 

 Even though we’ve been starting over since the beginning of time, it still can be a scary experience. Remember to celebrate each small win along the way, and allow yourself the grace necessary to grow

 After all, Career 2.0 should be about passion and delight. So above all remember to enjoy yourself.



One study from the American Institute for Economic Research (AIER) found that 83 per cent of people over the age of 47 who pursued a career change were successful. Of those success stories, people largely felt happier, less stressed, more passionate, and “emotionally, like a new person” after switching careers.

The study confirms that it’s never too late. In particular, this research finds:

• Out of the older adults who are trying to change careers, most are successful.
• The majority of successful career changers report that the move has made them happier.
• Many successful career changers report that the change increased their income.
• Transferable skills are among the most important factors in successfully changing careers.
• Workforce services, personal attitudes, and social support systems also play a role in the success of career changers.

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About The Author

Cheryl Grace | Lifestyle Expert

Cheryl Grace | Lifestyle Expert

Cheryl Grace is the CEO and founder of Powerful Penny LLC, an executive coaching, consulting and lifestyle firm that provides empowerment resources, online courses, workshops, and executive coaching services. A former SVP at a global corporation, Cheryl has refocused her work from successfully transforming corporate reputations to transforming individuals striving for next-level advancement. She has been seen on Daytime Chicago and CBS This Morning. Additionally, Cheryl is a 2022 Women of Color Innovator Awards recipient, has been profiled in Essence and Forbes, and has been named one of Black Enterprise Magazine’s “50 Most Powerful Business Women,” a “Remarkable Person” by the Chicago Tribune, and a “Distinguished Alum” by Purdue University. Signup to receive Cheryl’s Level Up with Grace Newsletter

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