#94 | 5.9.25 - Q&A: Is It Time to Quit? / How to Stand Up for Yourself More Effectively / Bye Bye, Bad Emails / List of Life Principles
Hello, friends, and welcome to Further Faster Fridays!
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A quick housekeeping note: 🧹
I’ll be out of the office next week, so expect the next issue on May 23rd :)
Now, on to the content!
Q&A: Is It Time to Quit?
I received an incredibly honest and brave question this week:
Dear Further Faster Fridays,
I've noticed in your last article we can submit questions, so here's mine... when do I know if it's time to quit?
For context, I'm 65 years old and have been running our family's real estate business for nearly three decades. My daughter joined the firm five years ago, and while she's doing wonderfully, I'm just not feeling the fire anymore. The early morning meetings feel like a chore rather than an opportunity. The market has changed so much with all this technology, and frankly, I'm tired of trying to keep up with the latest Instagram house tours and virtual walk-throughs.
Some days I dream of just spending mornings in my garden and afternoons with my grandkids instead of negotiating contracts. But then I worry - am I just having a bad month? Will I regret stepping away from what I've built? How do you know when it's really time?
I'll leave it at that. Thanks so much for your insights!
Warmly,
Martha
Wow, thank you for your thoughtful and incredibly brave question, Martha. First, I want to acknowledge the courage it takes to even ask this question after dedicating three decades to building your real estate business. The struggle between honoring your legacy and honoring your changing needs is no easy task to navigate. Well done on getting some outside perspective! 👏
A couple of things I noticed in your question:
1️⃣ Your shift in energy
You mentioned not "feeling the fire anymore" and that morning meetings feel like a chore rather than an opportunity. It’s possible this waning enthusiasm isn't just a passing mood - it could be your inner wisdom speaking.
2️⃣ You have a compelling vision for what comes next.
Your garden and grandchildren aren't just escape fantasies—they represent genuine sources of meaning and fulfillment that deserve space in your life.
What To Consider Next
I would recommend taking a week to reflect on your current leadership role. Create two simple lists: what still energizes you about the business, and what consistently drains you. Consider discussing your thoughts with a trusted colleague or friend who knows both you and the business well. You may also consider using the decision matrix I previously wrote about.
If you decide it’s time for a change, since your daughter is already involved in the company, perhaps consider a phased transition that allows you to gradually step back while mentoring her in areas where your experience remains invaluable. This isn't an all-or-nothing decision. 😉
Remember: Choosing to step aside isn't failure—it's the ultimate act of leadership to recognize when a transition would best serve both you and the organization you've built.
Again, I appreciate you sharing this deeply personal question with our community, Martha. Your willingness to reflect honestly on this transition sets a powerful example for other leaders facing similar crossroads.
I wish you clarity and peace in your decision! 🙏
Tyler
PS - If you are interested in submitting a question, click the link below or reply to this email 👍
How to Stand Up for Yourself More Effectively
There are some great pointers in this article, all without turning into a difficult person to work with.
Bye Bye, Bad Emails
Justin put together a great infographic with practical tips on how we can all improve our emails ✅
List of Life Principles
This is an older list of life principles, but I was reminded of a few of these this week. Thought you all would enjoy reviewing them.
“Who you associate with is just enormously important. Don’t expect that you’ll make every decision right on that, but you are going to have your life progress in the general direction of the people that you work with, that you admire, that become your friends. You want to hang out with people who are better than you are because you’re going to go in the direction of the people you associate with."
- Warren Buffett