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How to ace your first workcation – tips & tricks

My friend and fellow startup CEO from SwipeGuide, Willemijn Schnyder, sent me a text: “Do you want to go on a workcation with me?”

What the heck is a workcation? I like working. I like vacation, but I didn’t think mixing it up would be a good thing. But hey, let’s be open minded!

Alright, let’s ask the Internet about “Workcation”: 

Your summer vacation doesn’t have to end if you don’t want to. … Mixing business and pleasure with a long-term stay, also known as a workcation, is one of the hottest travel trends today. – Washington Post – 29 July 2021

Alright, hot trend 🙂 

Running a startup is relentless and can feel like “whack-a-mole”. You know you have to work on the business but reality it’s mostly working in the business. It really helps to talk to other founders for p2p coaching. A lunch, walk or drinks are great but I always wished after each meeting we had more time to dive deeper into topics. 

Would a workcation help busy startup CEO’s?

I already took two weeks off for a vacation/digital detox and went sailing in Greece in June, so it felt a bit indulgent to jet off again. Particularly since the business is growing nicely. Can I afford to take time out? 

I asked one of our investors for advice and she said immediately: “Go!. Why don’t you stay for a week in our holiday home in Italy? We just worked there ourselves during the summer so you both have a workstation”. 

Perfect! 

So how did it go? 

The week was really productive and mentally rejuvenating. We got up early, started to work at 7am. Did our team standups, clients calls and work on  running projects. We closed the laptop at lunch. 

In the afternoon we walked, talked, or went boating. Being in places with a wide open view or where we could move our bodies. Staying near Portofino, its national park and coves, gave us a different perspective. Each day we talked about a strategic topic, challenged each other on how to build culture, deal with investors, our role as a CEO, mental health and personal development. 

We learned a lot, deepened our relationship, gave some tough love and also went into practical details, for instance prospecting, sales processes, hiring and tools. 

My advice to get the most out of your workcation:

  1. Stay in a home in a quiet place with proper workspaces and a kitchen
  2. Check the wifi speed and upgrade with a booster on day 1 if needed 
  3. Explain to your team the goal of your workcation and set boundaries on availability 
  4. Co-create a list of topics to discuss to get most out of your time together
  5. Get active and move your body more than you would at home 
  6. We stayed for 7 days. For the next workaction I would do 4 days.
  7. We had a friend in the house who cooked wonderful meals and joined the evening program. Highly recommended since we could just focus on our conversations and stay in a private place not having to worry about booking restaurants. Also a lot cheaper. 

The Verdict?

It may seem like a workcation wouldn’t be very relaxing, but I came back with a tan and tons of ideas and energy.  Highly recommended! 

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