Should You Quit?

Headed into the holidays with people who are going to have opinions about your chosen life's path?

Yeah, me too. So, this week's email is chock-full of my thoughts about this whole -- waves hands expansively -- situation.

First, we need to define success for ourselves.

I used to have this crystal-clear idea of what success was supposed to look like—who I was going to be and who would make my parents proud. I thought law school was the path, but when I got there, it was nothing like the courtroom dramas on TV. It didn’t take long for me to realize that this wasn’t my dream; it was someone else’s. So, I dropped out.

In a recent Yahoo Finance interview with Tiffany "The Budgetnista" Aliche , I shared that if I’d chosen a trade instead, it probably would have been painting. And while I didn’t end up holding a gavel or a paintbrush, I learned an important lesson: for decades, we’ve been told to pick a major, pick a college, pick a trade, and GO. But how often do we stop to ask: What does success actually mean to me?

If you’re a young adult deciding which path to take, here’s my advice:

1. Stop following your passion.
2. Instead, ask yourself two questions: “What would I do if I knew for sure I would fail?” and “What’s so interesting to me that it’s worth struggling through the hard parts?”

If you’re mid-career and thinking about a pivot, start by getting clear on your “need-to-make” number (the minimum to cover your basics) and your “want-to-make” number (your aspirational goal). Then, start having conversations—network, do informational interviews, and learn everything you can about what that next chapter might look like.

Take 24 minutes to listen to the full Yahoo Finance interview, and share it with anyone sitting at the holiday table who’s weighing big decisions about their future. Because no matter where we are in life, we owe it to ourselves to ask the big questions: Who am I now? What do I really want? What’s next?

And another thing before you quit your day job…

Are you running toward something or away from something?

Ohhhhhhh, snap. That's a big question, huh?

The holidays: a time for family, reflection, and—for some—rethinking their careers. But should you quit your job now, during the holidays?

As I shared on NewsNation, quitting your job during the holidays isn’t as wild as it might seem. But before you make the leap, it’s important to weigh both the pros and the cons.

First, the pros: If your current role is crushing your soul, compromising your well-being, or leaving you utterly disconnected, the holiday season can provide the perfect moment to reflect, reset, and recharge. Use this time to think about what you truly want from your career and network at all those holiday events. The end of the year also has a way of shining a light on what matters most, helping you align your next steps with your values.

But the cons? They’re real too. Financial uncertainty, a lull in holiday hiring, potential gaps in benefits, and the risk of jumping from the frying pan into the fire (by taking a less-than-ideal job out of pressure) can’t be ignored. That’s why I always advise having at least six months of savings to cover your “need to make” expenses before you consider leaving a job. And remember, decision-makers tend to be out of the office this time of year, which can slow down hiring processes.

One critical insight from our research: bad leaders bleed out good people—we know this. But even if you work for a “good” leader, if you lack a meaningful relationship with them, you’re just as likely to leave. If you’re thinking about quitting, or if you’re a leader trying to retain great talent, focus on relationships. For leaders, that means asking your team what they care about and how their values align with their work. For employees, it means leaning into connection—yes, even in the break room or during casual conversations.

So, The One Thing to do this week is to get clear on what success means to you. Ignore the opinions of others, and ask yourself: What’s worth the struggle, and what lights me up enough to push through the hard parts? Let this clarity guide your conversations and decisions.

By the way, I've been running this assessment since January 2019, which is nearing 10,000 responses. Take a few minutes -- about 15, really -- and give yourself a user's manual to your career. I'll send you the results, along with everything you should be doing, right now, to make the most of this one big juicy life.