“This post may contain affiliate links. Please read my disclosure for more info.
Have you ever made a significant life change where you had no idea whether it would work out? One that just felt right at the time, but left people close to you scratching their heads?
Maybe you were leaving something you knew wasn’t right, or reaching for something that you weren’t sure would work out. You weren’t prepared. And you hadn’t worked out the details, but you said yes anyway.
Or maybe you feel stuck now. This isn’t what you expected. And it doesn’t look like anything’s gonna change anytime soon.
Sometimes our illogical, but heartfelt choices end up as pivotal moments in our life.
But how can you tell when you’re at one of those moments?
How to tell when it’s time for a major life change
I recently heard Jon Stewart describe a time like that during an interview with Howard Stern. Jon hosted the Daily Show on Comedy Central from 1999 to 2015. He’s interviewed everyone from U.S. presidents, to senators, to various newsmakers. And in the process, he’s earned twenty-two Emmy awards in sixteen years.
At one point during the interview, Howard asked him, “what’s the one thing you’re most proud of, over the course of your career?”
Jon replied, “that I just did it. That I packed up my shit and drove to New York City and went for it.”
So it wasn’t any of the Emmy awards he was most proud of. It wasn’t hosting the Oscars twice, or the White House correspondents dinner, or interviewing hundreds of the most influential people around.
He was most proud of one single decision he made at age twenty-three. To pack a bag and leave familiarity behind.
And it wasn’t to take a 9 to 5 with a 401k and health benefits. It was to try his luck doing stand-up comedy in the New York City clubs for the 2am crowd.
There was no contingency plan. His only plan was to try and reach for something different.
In fact, he described this as a pivotal point in his life. After graduating college, and working a variety of jobs, he began bartending at the legendary City Gardens in Trenton, NJ where bands like the Ramones, REM, the Butthole Surfers and Sinead O’Connor regularly played.
“Finding this place City Gardens was like, ‘Oh, maybe I’m not a giant weirdo. Maybe there are other people who have a similar sense of yearning for something other than what they have now.’ I think it inspired a lot of people, man. It was a very creative environment. It was a place of great possibility.”
So when he left the bar, packed a bag and drove up the Jersey Turnpike, the idea of becoming an MTV host, or a late night talk show host was the furthest thing from his mind.
But sometimes you don’t need to know 3 steps ahead. Sometimes you just need to know the next right move.
The next right move isn’t always about money. And it’s likely to be downright scary. But when what our heart wants becomes stronger than our fear, we know it’s time to make a move.
Are there signs that might give us a hint that it’s time for a change?
4 Signs you may be ready for a business or a personal life change
1. You're Not Committing
When I began working in IT, I was eager to advance by learning as much as I could. But honestly, I found some of the things my manager encouraged me to study, just out and out boring.
At one point, our office hired an IBM consultant named Mike to help with a project. Mike was a salesman, but he could also install a mainframe system, setup networks, and troubleshoot complex problems. I asked him one day, how he was able to gain so much knowledge in a fairly short time.
Mike laughed and said, “you have to get intimate with it”.
He was joking, but he meant that with anything you value, unless you’re willing to put in the time to live and breathe all the nitty gritty details, you’ll never understand the bigger picture.
Granted, some stuff is boring, frustrating and repetitive, but if you’re consistently finding it difficult to immerse yourself in the details, then maybe it’s not something you truly value.
2. You've Been Playing it Safe Too Long
I’ve seen several long-time, well liked employees called to HR for a “meeting”, from which they were then escorted out, not even permitted to gather their belongings. Coworkers had to bring their coat and car keys, then ship their belongings home in a cardboard box.
Their performance was fine. But no notice. No warning.
Just, “Sorry, you’re done…here’s the door“.
The days of working somewhere for thirty years, then retiring with a huge dinner party and a gold watch are gone. Most people will work 7-10 jobs in their career. So, assuming your job is safe because you have seniority, is dangerous.
Having a routine might feel comfortable, but it’s also not very inspiring. As Roy T. Bennett said, “comfort zones are where your unrealized dreams are buried.”
If you knew your life would end next week, would you be satisfied with what you’re doing now? Is there anything you’d regret not doing?
3. You Feel Like You're Running Uphill Every Day
Spending a big chunk of your life on anything, business or personal, should be worthwhile and satisfying.
Sure, we need to invest the time and pay our dues to become proficient at anything. But if you’re constantly walking on eggshells, or chasing down emergencies, then it’s tough to roll out of bed motivated month after month.
Or when you sit in meetings all day, then return to 150 new “urgent” emails, it’s difficult to bring any creativity to your work.
Work (or life) should be challenging, but also fulfilling. You may have started down this path with a certain understanding, but things change. Sometimes we need to decide whether to adapt, or choose a different path.
4. You Feel Obligated, not Motivated to Stay
Bronnie Ware, a palliative nurse, wrote a book called, The Top Five Regrets of the Dying. In it, she describes conversations with patients who, during their last days, talked about their biggest regrets in life. The one regret expressed most often, was living their entire life by other people’s expectations – not what they originally envisioned.
Somewhere along the way, or maybe due to a slow series of decisions, we put our dreams in our back pocket and follow the best paycheck, the shortest commute, or remain on a career path only because we spent money on a degree.
Maybe you have a law degree, but hate being an attorney. Or you’re a business analyst but wonder if you’d feel more inspired teaching high schoolers how to become financially independent.
Do you have a plan for the next five years? What would your ideal life look like five years from now? What would you need to change to move in that direction?
There are certain pivotal moments in life that we have no control over. The death of a family member, being fired or divorced…
There are also pivotal moments that we do have control over, but only if we’re open to the signs.
Is the anger or the tension you feel really from the guy who cut you off on the way home?
What may have seemed like the right move three years ago, probably didn’t change overnight. The situation may have eroded slowly over time.
One way to discover what you need to change might be to keep a journal, with an emphasis on noting the positives and negatives of each day.
After a few months, look for patterns. Do most of the negatives revolve around work? Or a particular part of work, or your schedule? Or a particular person?
What would it take to increase the positives and change the negatives?
The goal is just to see what is, and isn’t working, and adjust your course to where you’d like to be headed. One that you won’t regret.
If Jon Stewart had tried stand-up comedy for a year and failed, he’d still have less regrets than if he sat in a cubicle for 3 or 4 decades wondering, “what if?” Instead, he listened to the signs, then took a risk, which in turn opened up possibilities he never expected.
Have you taken the time to listen to the signs in your life? It may seem difficult to replace what’s not working now, but it could be a lot more difficult down the road to replace what you once were.