How I Made the Switch to “Work Hard, Play Hard”

Instead of being the typical Silicon Valley workaholic

Even before Covid-19 was thrown in the mix, a shift was underway in the way we work. Whereas for many years people worked 9-5 and then clocked out for the day, we’re seeing a move towards blending our “home life” and “work-life” in a more flexible way–while still aiming to achieve an ideal work-life balance.

Some call this “work-life integration,” but essentially, it means giving those things that matter to you personally–like your family, hobbies, and self-care–the time they deserve, alongside your professional commitments. Or, as I wrote in a recent article for Fast Company, putting more emphasis on “life” in “work-life”.

For some, this could mean blending their “home life” into their traditional workday (like getting up early to work a few hours, then pausing to take the kids to school and go to the gym before returning home to get back to work again), while for others it could mean sticking to the traditional 9-5 schedule with evening and weekends as “playtime”.

However, what if you’re still struggling to find your ideal work-life balance? ⚖️ Although the work-life integration idea has, in theory, made our days more flexible, the outcome is commonly a lack of balance rather than more balance. When you’re working from home, it’s easy to cram a few extra hours in when you would normally be commuting, or get tempted to work while also trying to spend time with your family.

As an entrepreneur, this used to be my struggle. Ten years ago, when I founded my first company, I had zero work-life balance. It was all work, no play. I was pulling long days followed by long nights–always burning the midnight oil. Somehow I made it work, but I teetered on the brink of burnout for years. Not recommended.

Fast forward ten years, and I’m committed to not making that mistake twice. After all: “all work and no play makes Jack a dull boy”. And, I’m pleased to say that in my experience as the founder of Charli AI, I’ve successfully shifted from 100-hour workweeks to a “work hard, play hard” mentality. I’m managing to make time for my many hobbies (Overlanding, offroading, and mountain biking)🚘🚵 , my family, and my own personal needs for downtime.

And it all started with a little car … little, but fast, and so much “freaking” fun. 🏎️😁

Unlike Overlanding, I’m not going to compare the vehicle to running a startup. 🙃 This is all about pure fun! Taking time away and enjoying the trails. For me, this was work-life balance and I had an absolute blast ripping up the trails in this car. FYI … It’s street legal as well.

The interesting point about the picture is that it not only represents the fun part of my life; but on that particular day, I had to take a phone call and check-in on work. And right at that moment, I had a rare cell phone connection. 📱😎

It dawned on me that I could effectively blend my life with work. I realized that I didn’t have to sit in an office 9-5, and that “fun” brought exciting diversity into my life. The fun parts positively impacted me at work. They provided me with more creativity and innovation and taught me more about interacting with people.

If you’re looking to make this switch, here are some practical tips to create a more harmonious work-life integration:

  1. Build the right team. You are going to have to trust them!

    Selecting, hiring, and working with the right team is so critical. I can’t stress this enough. Rather than try to do everything yourself, it’s important to hire people with complementary skill sets (and personalities) who you trust will get the job done. If you want more work-life balance, you need a team you can rely on, even in the most difficult moments. It’s a team that cares and a team that works together. For me, the beauty of startups is that they tend to attract some of the most passionate people who are committed to the product—and who also want to see big success.

    Now that you’ve assembled a group of amazing people, let them do their jobs. They are better at it than you. And they don’t want your interference. Step back and let them do what they’re best at. As a leader, you need to focus on strategy, execution, problem-solving, and coaching/mentoring. Don’t micro-manage—it’ll stress you out, distract you, and generally piss everyone off.

  2. Stay focused on execution. The strategy is nice but you better execute!!

    The fastest way to burn yourself out is by chasing shiny objects and getting stuck in a constant loop trying to prioritize new things. It doesn’t take long before your constant creativity and innovation get in the way. This is a recipe for a 100-hour workweek and burnout—including burnout for your team. Instead, put your energy into big picture items like scaling the business, monitoring cash flow, making decisions on investments to grow your business, and so on.

    Also, spend time guiding your team so they can understand what you want them to prioritize, leaving you with more time to keep the commercial aspects of your business healthy. I’ve seen a lot of founders struggle with this piece because they’re so focused (and passionate) about the day-to-day product development. I have also seen a lot of founders and leaders look at execution the wrong way. Execution is not about doing more; it’s actually about doing less. Doing less but excelling at it! Descope the work and give your team the focus they need to be brilliant.

  3. Deal with it in the moment. You’re going to have to get organized!

    Procrastination is a huge time-suck. How much time has been wasted reading emails, flagging them, putting them aside, worrying about them, reading them again, and finally actioning them? How about all those little tasks that get added to the never-ending to-do list, like filing paperwork, organizing expenses, or managing documents? And then there is the messy desktop or cloud storage— full of files and folders tucked everywhere?

    That clutter has to go away. Permanently.

    It took a long time to get into a habit. But I have eliminated the noise. As I’m writing this article I have only 2 unread emails in both my work and personal email accounts. And these two emails I have to deal with today. The challenge was getting organized and figuring out the “tricks” on how to delegate to the team, deal with the issue right away, or more importantly how to disregard s%^t. And disregard isn’t tossing it out. I may need it in the future. Disregard is about getting it organized so that I can find it when I need it—out of sight, out of mind, and moving on to the top priorities.

Continued help and reinforcement

I still need help from time to time and rely on the team to pull me back. I’m still a workaholic and enjoy work too much to let it go completely. But I’ve learned to work hard and play hard—by comparison to what I was like 10 years ago, this is so much better. 🥳

The actions listed above are helping me achieve the work-life balance that I want. This hasn’t just been a small change, it’s been a lifestyle shift. It’s also the driving force behind the passion to get Charli to the point of keeping me organized and reinforcing the lifestyle.

Are you struggling with this? Do you have any advice of your own you can share with others? Please leave your thoughts in the comments.

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