Understanding Entrepreneurial Guilt When Going on Holiday

Welcome back, everyone. Today marks day 1152 of my Diary as a Runpreneur, and our topic is a rather timely and personal one: the feeling of entrepreneurial guilt when going on holiday.

As I sit here reflecting, it’s early in the morning. I started my run today at ten to six, knowing I have a plane to catch to Germany for a week's holiday. It’s been a whirlwind lately—I was just in Ireland celebrating my mother-in-law's 70th birthday, had a day at home, and now I'm heading off again. After Germany, I’ll be home for ten days before heading to Cyprus for a two-week break with my family. Lots of holidays, indeed, and I live for these moments.

Why do I call it entrepreneurial guilt? It’s a specific kind of guilt many of us entrepreneurs experience. On the one hand, I cherish these holidays. They mean everything to me. My life is governed by a money system, which might sound strict, but it isn't. It allows me to do what I want, when I want, and it ensures long-term financial security. But here’s the catch—I feel guilty every time I leave. My team is back home working hard. Although I work intermittently while away, checking on things, there’s still this nagging feeling.

Why do I feel guilty? For one, I care deeply about my team and their well-being. I’ve worked hard to build packages that allow them to take holidays and enjoy their lives. Secondly, there’s always more to do. And when I say “work,” it’s probably not the best term because I love what I do. It’s my passion, my purpose. My work is my life, and striking a balance between work and personal life is more about integrating both into a lifestyle I love.

Right now, we’re transitioning from an operating system we’ve used for over ten years to a brand-new one built from scratch. It’s a massive undertaking, presenting numerous challenges. My role requires me to ensure we’re on the right track, making my presence feel indispensable. So, stepping away brings its own set of worries.

But here’s the thing—holidays are one of my highest values. I do what I do for my family and for creating memorable experiences with them. It’s one of my 'whys'. Some might argue against having several 'whys,' but at the end of the day, my overarching reason is my family’s legacy. Looking out for future generations is my ultimate goal. So, spending time with family and creating these precious memories is incredibly important to me.

Every time the guilt sets in, I remind myself of my 'why'. I’ve put in the graft, spending years building these businesses with little to no holidays. Now that I’ve reached a stage where I can afford these breaks, I should fully embrace them. I can monitor things remotely, and my capable team can hold the fort in my absence.

So what’s my key takeaway? If you’re feeling guilty about going on holiday and leaving your team or work behind, remind yourself of your 'why'. If holidays with family or personal downtime are intertwined with why you work so hard, don’t let guilt overshadow your joy. Rest, recharge, and come back stronger to continue your entrepreneurial journey with renewed vigor.

Thank you for joining me on this reflective topic. Any questions or thoughts? Drop me a line, and I’ll respond to everyone. Don’t forget to subscribe, share, and comment. The more people we reach, the more funds we raise for saving children’s lives through my ultimate ultra-marathon challenge. All the details on how to get involved are in the link below.

Stay positive, stay happy, and I’ll see you again tomorrow.

Best regards,

Kevin Brittain