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RE-CAREERING: Why I Did it and Why You Should Too

Jennifer Bliss standing on a wooden bridge with her guitar

Well, let me clarify my statement. If your career is totally satisfying personally, professionally, socially, mentally and economically… this may not be the article for you. But if this is NOT you, there may be some insights I can share that could help change your life for the better. 

So how did I go from full-time musician in Atlanta with 20+ years in the industry, to working remotely from my hometown of Cleveland making more money with less stress than ever before? I “Re-Careered.” To be clear, I did this slowly, reluctantly and with a lot of “real talk” conversations with my family and with God. 

But if I knew then what I know now, I would’ve done it a lot sooner.


I’m a great musician. I had worked a 9-5 while playing professionally for years, but when the opportunity came to go on tour with a major R&B artist, I went for it and never looked back. I played all over the world, recorded, produced, wrote and even taught music. I loved what I did and was loved for it. It’s almost as though my identity was exclusively defined by my career as a professional guitar player.  I couldn’t see myself doing anything else. But all that glitters isn’t gold.

What you don’t see is that after that tour, or that spot date, or that TV appearance I was left with the financial insecurity of a feast or famine kind of economy. It’s important to note that this kind of income instability is not exclusive to musicians and artists. 

Just ask any commissioned-based professional, gig or contract worker, or those of us who are self-employed… and we’ll tell you. It’s one thing to go to a job with a guaranteed steady paycheck. It’s another thing to not only do the work, but market the work, secure new work, net-work, and hope more work comes your way. It may be difficult to admit, but for many if not most, this type of economy is a recipe for “survival-mode” living. A career on continual life-support. You’re not dying, but you’re not really living either. You definitely may not be prospering. 

I’m not saying these types of careers are impossible in the long term. But where I’ve seen it work best were in two-income households, where the self-employed or contract worker’s income is supplemental. The monthly bills were consistently covered by the “straight job” worker, while the gig worker’s income paid for the extras.

This was not the case for me. At best, I was just getting by and at the end of the day, my dollars weren’t making cents. #PunIntended  

Jennifer Bliss in a pink spotlight with her guitar


Some jobs take a lot of energy and physicality that you just might not have in you during this season of life. Maybe you have health issues that make your work more draining. Maybe you have to be a caretaker for an aging parent (my case) or other loved one. Maybe the travel is too much or the hours are too long. Maybe the work environment is socially and emotionally toxic.

Maybe your industry is evolving or devolving to where it doesn’t suit you anymore. Maybe there’s a glass ceiling that you just can’t control or push through. Maybe you’re just settling for “what is,” but too tired, intimidated, or set in your ways to reach for “what could be.” 


Here’s my very long story short: Covid hit, no more gigs, lockdown approaching, prospects uncertain, sold house, drove across states to live with family and figure out my life, started online business, ran out of money, hit rock bottom. My work wasn’t working. Finally ready to RE-CAREER. 

After letting go of my pride and fear and putting on humility and determination, I revamped my resume and pounded the pavement for a J-O-B. Due to health and family reasons I needed something where I could work from home. After grinding for three months, I found an ideal entry-level remote job that had great training, career growth opportunities and paid more than I ever (consistently) made in my previous self-employed career. Is it as sexy as performing on stage? No. But it does have Paid Time Off, a matching retirement plan and health benefits. What’s even better is now I can supplement my income with doing music on my OWN terms. 

My new full-time job is fantastic and everything I needed for this season. I’m still astonished by how less stressed my life has become. I see an exciting and prosperous future ahead of me. But it all started with that pivotal decision to try something new… to RE-CAREER. 

Your journey may be different, but where are our journeys the same? 


  • Am I too scared to admit that my work isn’t working? 

  • Have I normalized “survival mode” living?

  • Is my career in conflict with my life’s priorities?

  • Are my family/friends concerned about my career prospects? Have they tried to talk to me about it?

  • Am I stressed, depressed, with dollars that don’t make cents?

  • Do I want something different, but have no idea where to start? 

If you answered “yes” to any of these questions, it may be time for you to RE-CAREER.

Seasons change, and so must we. What season are you in? If you’re going to work, it might as well be for something that work$ for you in THIS season.

Don’t limit yourself to one career like I did. Try something new and give it your all. You may just find, as I did, that life’s better on the other side. 

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