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50 Ways to Leave Your Employer to Launch Your Own Gig After 60

By Donna Kastner December 19, 2022 Managing Money

Sometimes inspiration comes from unexpected places. One morning, I was working on this post, but the concepts weren’t gelling. Rounds of writing, editing, deleting and starting again from scratch ensued.

Then, like a gift from heaven, Paul Simon’s 50 Ways to Leave Your Lover started playing on Pandora, and my writer’s block vanished, as new thoughts emerged…

Just slip out the back, Jack.
Make a new plan, Stan.
Don’t need to be coy, Roy – just listen to me.
Hop on the bus, Gus. Don’t need to discuss much.
Just drop off the key, Lee and get yourself free…

Before we go any further, I want to make it clear – I’m not advocating Paul Simon’s 50 Ways as your best roadmap to resign, but there were glimmers in that song that sparked thoughts on exiting strategies.

Humility aside, resigning gracefully is one of my strengths – not by design, but by necessity and practice.

True Confession #1: I’m a Serial Resigner

As I scan back over my 38-year career journey, it’s a patchwork quilt of diverse work pursuits, filled with plenty of resignation moments. On each occasion, there were also sleepless nights as I considered how I might convey such news in a candid, constructive and compassionate manner.

In 1979, I started my career as a high school band director in Ohio. Upon completion of my first year, my husband was relocated to Michigan. I managed to land another assignment, only to leave a year later, prompted by another relocation – this time to New Jersey.

In 1984, our son was born, and I chose to take a one-year sabbatical to figure out my next career step. While teaching was something I loved, the financials were difficult to reconcile. My teaching salary would largely be allocated to cover child care expenses, so I purchased an IBM PC Jr. and started a home-based typesetting business.

Within the first year, I recruited a half-dozen contractors who would typeset book manuscripts from home. Happily, I was making much more than I did as a teacher, with a more flexible schedule that would accommodate my new role as mom. Guess what happened next?

Another relocation. All told, there were nine moves in 15 years. Then we landed in Cleveland and thankfully, the relocations stopped. Through the years, I’ve toggled back and forth between jobs and entrepreneurial endeavors.

While it’s much easier to resign due to a spouse’s job relocation, there were a half-dozen resignations that were prompted by my own choice. Either the culture changed, the job changed or I changed, and so the job was no longer a fit. Those resignations required a bit more finesse and planning on my part.

Through each resignation, I strived to leave on the best of terms, giving plenty of notice and going the extra-mile to train my replacements. Happily, most self-imposed resignations prompted the same question: “What more could we do to keep you?”

I share that not to boast, but to emphasize that extra-mile players who resign gracefully are remembered fondly. Now, about that headline: 50 Ways to Leave Your Employer…

True Confession #2: You’re Not Getting 50 Ways in This Post

Sure, I could brainstorm and come up with a whimsical list of 50 that might make you chuckle, but they won’t be helpful as you prepare for your own resignation moments. So instead, how about five that matter?

Be an Extra-Mile Team Player and Lifelong Learner

As a blog reader, you’ve already demonstrated a strong appetite for learning and personal growth. Still, that attribute is in short supply today, and many employers notice this more than you realize.

Alas, that’s often not evident until the goodbye conversation. If your track record of performance is strong, while they’ll be sad to see you leave, this resignation conversation should happen more easily.

Don’t Burn Any Bridges

There might be a misdeed or two that contributed to your decision to resign, but revealing it now has more downside than upside. Let it go and do everything you can to stay positive.

For many, a previous employer could become a future client. Past employers are also good referral sources for new business opportunities.

Find Something You Appreciate About Your Employer

Thankfulness soothes the resignation sting, but you need to make it real. Think hard and find something – or someone – you truly appreciated at this company and share it. You’ll be amazed at how this affirmation diffuses any tension as your employer processes the news.

Be Ready to Share More About Why You’re Resigning

You can bet your employer will ask about the reasons behind your resignation. For most, launching your own business will be well received.

One of my trickiest resignations happened amid a series of mergers. The culture was changing rapidly and so was my role. For me, it was cathartic to list every reason on paper. Then I winnowed down my list to things that were less emotionally charged.

Ultimately, I acknowledged that the business needed to move in another direction to compete on the market, but this new direction wasn’t aligned with my strengths. Life is too short to wake up most mornings less than delighted about the work you do. Who can argue with that logic?

Keep in Touch

After the goodbyes on the final day, I’ll send handwritten thank-you notes to colleagues, often calling out something I appreciated about them. Reach out to connect with colleagues on LinkedIn, too. I’ve had some great referrals come from people who read something I posted on LinkedIn.

While everyone has the best of intentions to keep in touch, go the extra mile and invite them to lunch every now and then. If you’re launching a business, your network will be a crucial business development accelerator, but it requires constant care and feeding and you must give as good as you get.

Let’s Have a Conversation:

Are you preparing for a job exit? Or have you recently resigned to launch a new business? What additional tips or insights can you share to help us all tackle this resignation exchange more gracefully? Please join the conversation.

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I love working for myself- you just have to work out your plan for insurance if you don’t yet have medicare. My husband was a teacher and didn’t make a lot of money, but his insurance covered our whole family, which was amazing!

The Author

Donna Kastner is founder of Retirepreneur, a collaborative community for professionals in their 50s and 60s, striving for a smooth segue from full-time job to part-time consulting practice. Through articles, videos, podcasts and workshops, Donna’s ushering in new conversations about blending work and retirement. You can visit her website here, or find her on Facebook and Twitter.

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