Work Weary Willa - Just Jill

Just Jill is the creation of Jill Cohen Morris. Jill is an avid rambler and married mother of two from Toronto, Canada with a remarkable zest for life and a fabulous sense of humor. 

Dear Just Jill,

I’m 52 and have been working for the same company for almost twenty years. My job is stable, I am very well paid and have great benefits.

Sounds close to perfect right? Well, here is the problem; I am not happy. I do not like what I do. I am bored and unfulfilled.

I do have some ideas on what I would like to do. As much as I am so excited about the prospect, I am also terrified.

Am I crazy to leave a secure job to follow a passion?? I need to think of my future and retirement. Would I be putting that in jeopardy?

Have any of you recently decided to completely change career paths? Do you have any regrets? I need advice from my wise Sole Sisters.

What’s a gal to do?

Sincerely,

Work Weary Willa

Sole Sister Advice & Comments

• I would first ask if you could work less and do what you love as a hobby.
  
  
• Go for it!! Find what lights you up! Yes, there are risks. The greatest risk is losing yourself to staying where you are unfulfilled. If it goes south, and it may, you will have your moments of regret for losing stability; absolutely, you will. However, as I've personally discovered recently, you won't regret not feeling unfulfilled, and that feeling will keep you going to find your career role that lights you up.
  
  
• I would look at the aspects of the job that are fulfilling - can you re-frame or re-focus on those and possibly pursue your passion on the side for now? Being bored is better than being stressed. Maybe you can condense your work week into 4 days to give you time to do the things that light you up.
  
  
•  Figure out what lights us up to do and where is definitely the way to go. It is great we are all different - some people enjoy jobs that some of us think are boring!
  
  
• I spoke with a financial advisor, and then I quit and left the country. I happily retired when I was 54 and I follow my passion for rescuing and fostering dogs (and a few cats). 
  
  
• I left my more than 30-year teaching career a year ago. I have absolutely no regrets. I still don’t know what to do instead, but it will work out somehow!! In the meantime, I am so much less stressed.
  
  
• My personal opinion is that you should stay with the job and do volunteer work that satisfies you.
  
  
• We all have to retire or leave an employer at one time or another. Pick your time and set your own destiny. Plan your exit strategy now. When I left the company I had been with for 27 years, I went freelance instead. I work full-time from home 40 hours a week, not a minute more. Pursuing all my hobbies the rest of the time. I take a week break every 3 months. Sometimes 2 weeks. I have less income and spend more (hobbies cost money!), but I am happy. Working keeps my mind sharp and pays for my medical insurance. Win-win.
  
  
• I left my corporate job to freelance, and although there is less money, the lifestyle benefits make it super worth it. I particularly like not having to get dressed in a suit every day or be in particular places at particular times.
  
  
• I was at a job for 10 years, and I loved it. But I moved to another company (same line of work) for better money, and perks and to work remotely from home. A good decision and I’m happy with it. Ultimately you need to do what’s best for you! It’s your life!
  
  
• I have done just that. I am working in a school, getting paid rubbish, but come September, I will start my part-time training to become a counsellor. Why? Because I want to do something that resonates with who I am and fills my soul—something meaningful. I am applying to volunteer and work part-time at a local garden, as I love spending time in nature and chatting with visitors and their dogs. Follow your heart. We only have one life; live it well.
  
  
• Go where your passion is! I too was in the same job for 24 years. I dreaded going to work. Went back to school at 47. Changed careers and now I'm very happy. While I don't get the same benefits as my old job, I would rather be happy than have the extras and be unhappy. Go for your dreams! Shoot for the stars! You got this!!
  
  
• How long do you have to be in the current job to get those retirement benefits? It might be worth it to stay for them. Also, start saving NOW in case your salary goes down. It is VERY hard to get used to having less money! Even if you are not a big spender, it is hard to have less coming in.
  
  
• Life's way too fascinating and yes, short, to spend it bored. Run! Do something that charges you up, that gives you life! Go!
  
  
• My husband changed his job after 35 years. We decided together that it was a good time. We had money saved up for a holiday during Covid that we couldn’t take, so he went to school, and now he’s in a job he really enjoys with more responsibility and respect. At 52, he was an apprentice. I’m proud of him, but he was afraid, nervous, etc., and now wishes he’d done it sooner. I, on the other hand, seem to change jobs all the time. I juggle 3 jobs, one permanent part-time and 2 side hustles.
  
  
• I say go for it, but be prepared first. Could you go part-time or use your vacation days to allow time to pursue /plan your next step? It's hard to find work while working full-time. If you have a pension, make sure you check the rules/penalties. Could your leaving be considered a retirement? Almost 20 years is a considerable amount of time.
  
  
• My advice is to do some careful planning (meet with a financial advisor if you can) and have a game plan before you leave. If you find that now is not the best time to leave your job, seek out a fun "side hustle" with the potential to (maybe someday) bring in a little extra income. Often, our side hustles help us discover purpose and passion and can lead to the next thing!
  
  
• Do it!! I've changed careers a dozen times. Initially, it can be scary, but it's also exciting and reinvigorating. It will fill your heart and expand your mind—life is not just about the paycheck. You will learn to live within your new means and feel a new lease on life. Go for it!!!
  
  
• Would you ever consider a side hustle? Dabbling into something you enjoy in the evening or on weekends? It could help make your full-time job more bearable if you think of the side hustle as the thing that feeds your brain and your soul while your full-time job feeds your family and your retirement fund.
  

SSR doesn't endorse the advice or content shared in this column. Our goal is to access the wisdom of our incredible Sole Sisters.

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