Saturday dinner. Everyone taking a turn, saying what happened that day.
Sometimes I would miss a fragment of a story. Sometimes an entire conversation. Only when the kids burst out laughing would I return to the moment.
It happened regularly. Central Park on a Saturday morning. A board game on Sunday afternoon. Anywhere, really.
First, I’d feel guilt and shame for not working. Then I’d feel guilt and shame for not being present for my family, my entire reason for not working. I would top it all off by hashing out all my tasks in my mind, one by one, over and over again throughout the weekend.
By the end of the weekend, I was more exhausted than if I had worked and spent time with my family and skipped sleep altogether. I expended more energy navigating my ruminations and emotions than I would have if I had done the work, which sadly, made me question why I had decided to stop working on the weekends in the first place.
It sounds terrible in words. But trust me, it was worse living it. I had already stopped working weekends. Six months earlier.
I shouldn’t have been surprised how deep this was woven into me.
I worked weekends for years. It started as a job requirement in investment banking, then became fun during my time in start-ups and media. I was consistently praised and promoted for my work ethic and results, which I attributed to my long hours, including late weeknights and weekends.
But as I started to build a family, it became a burden.
I wanted to cut back on my weekend hours. In fact, I wanted to stop altogether, but I just couldn’t.
The voices in my head were adamant: “If I didn’t work, I’d fall behind. I would let my colleagues and team down. I’d be unworthy of my leadership post. I would fail.” They created a rationale my brain felt safe holding tightly.
Eventually, nearly a decade after I had the inkling to stop working on the weekends, I did. It wasn’t easy.
When you have built your habits around a belief system that is guided by fear, you’ve built a cage out of habits you mistook for protection.
Persistence, patience, and some self-recognition.
So how did I eventually stop working on the weekends without tormenting myself? Just as I constructed the habit over time and with a mixture of fear, belief, and positive reinforcement, I needed a recipe with multiple elements.
The first and perhaps the most important ingredient: persistence.
I just kept at it. As adamantly as my mind messed with me, I was just as immovable about staying the course. Each time my internal saboteurs reared their heads, I would provide a counterargument and stay the course. I reminded myself how important my family is to me. I also wanted to give myself space away from work themes to refresh each week.
They were good reasons, but it was still hard to keep at it. So I needed another ingredient: patience.
When I found myself tensing up instead of relaxing into playtime with my daughter, I would have to remind myself, “the work will be there Monday — it’ll be OK.” The grace I gave myself was probably one of the main reasons I could persist.
My patience also extended to how I measured time and my progress. As someone highly motivated by goals, deep behavior change like this is hard. The roadmap is vague and without a clear endpoint. Milestones are hard to predict and even harder to measure. I needed to be OK with all of that and still keep going.
Which leads me to the last ingredient: self-recognition.
This is the part of the process high achievers tend to avoid because it feels cringe-worthy. Acknowledging your wins and giving yourself a pat on the back can feel ridiculous at best and embarrassing and a waste of time at worst. But rewards and recognition matter. What I found was that naming the small wins made the next week easier. That’s how I primed myself to make real change happen.
For me, self-recognition was mostly positive self-talk: “great job staying the course!” I found it so much easier to change how I spoke to myself than to formally reward myself. I’m not someone easily motivated by material things. I much prefer emotional rewards. The key was to not skip this step. Celebrating myself and my commitment made it easier to keep going, especially when the finish line wasn’t visible.
It took 6 months for the voices to quiet. Nine months before I actually enjoyed my weekends. More than a few times, I reconsidered my entire approach. I love pursuing goals, but I couldn’t see the goalposts on this one, and uncertainty breeds the worst kind of doubt. I had to trust far more than I was comfortable with.
Start with small, clear steps.
The routine I created for myself was simple.
Before shutting down on Friday, complete a 10-minute reflection:
What went well for the week?
What could have gone better?
What are the biggest boulders to move Monday?
Remind myself why I’m choosing not to work on that weekend
That’s it. Shut the laptop. Turn off notifications. And when the rumination and guilt come calling, be ready to recommit to my why.
After each weekend, I would complete a 5-minute reflection:
How many times did I catch myself ruminating or feeling guilty? Those were all wins!
How many times did I bring myself back to the moment? Another set of wins!
A mini-internal celebration for completing another weekend! 🙌
And truth be told, I didn’t skip work every weekend. There were seasons of strategic planning, end-of-year reviews, or big deals when I allowed myself to work. But there was the difference from the past: it wasn’t driven by fear; it was intentional and time-boxed.
Your turn.
My challenge was working on the weekends. Yours might be entirely different. But how deeply it’s ingrained in you might be the same. Habits form over time and with evidence of their validity, even the ones that no longer serve you.
If you’re contemplating a shift, or deep into the process of making one, don’t let the hard days or tough months stop you. You’re making more progress than you can see; stay the course. Your future self will thank you.
May you lead without limits,
If this piece resonated with you, consider giving it a ❤️ so more people can find it on Substack. And if you know of a leader who would benefit, please consider sharing it with them.
And if you’re someone who has conquered a habit that was no longer serving you, I’d love to hear about it. Consider sharing it in the Comments or write to me directly. You never know who you might inspire to do the same.
I write every week because I want more ambitious, heart-led leaders to feel less alone and better equipped to reach their full potential. Thank you for being part of the journey with me.
Work with me
If you’re looking for support to make a shift, I have 2 one-on-one coaching spots opening up for the Fall. And if you have a team looking for a speaker or facilitator, I have 1 spot open for the fall. Book time with me to learn more about how I help leaders in their career, leadership, and mindset.
And if you need a respite from the daily grind to figure out your next career step, there are still spots available for my Career without Limits Retreat in November. Learn more here.