Making the most of your spare time: Holidays and Travel

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One of the great things about your portfolio executive workstyle is, if you set it up correctly, it can be a really powerful platform for having different experiences of holidays and travel.   

Think about it this way, you can organise your life so that your holiday is booked out with your clients and they know that you are going to be away.  They are used to the idea that their employees take holiday, they should be used to the idea that you as a portfolio executive take holiday.   

Plan your holiday dates out at the beginning of the year and then if you want to go and do the trip of a lifetime, perhaps a whole month or six weeks traveling, then think about how you can continue for some of that time to sustain your client relationship.   

In February this year, I went and spent a month in America. During that month I had two weeks Washington DC, a week on the West Coast in California and another week in Alaska.   

During that period, I was able to serve all of my clients and the way I did that was to shift some of the people at the beginning and the end of that period so that they had either has some of their meetings a little bit earlier or a bit later. I also to have a strategy where the meetings I did have allowed me to engage with them before my holiday day started and it suits me to get up at 4 o’clock in the morning and do four hours work before 9am in the morning and then have the rest of the day free as holiday.  Maybe you’re not constituted the same way, but perhaps you can do something at the other end of the day, so if you want to go on that four to six week break then it is entirely feasible.   

For many years, we would take a month in the Canary Islands every August and I would commit to joining my wife a few days later and leaving a few days earlier, which suited her, so I was just out of company country for three weeks and then during one of those weeks, I would do some work in the mornings but the overall experience was a whole month family holiday, even though for some of that time I was spending two or three hours a day doing some work.   

Perhaps for you, it’s about more long weekends, more mini breaks – we talked about the ideal working week in an earlier blog. Or maybe it’s the holiday of a lifetime.  I was really intrigued by the offer there is now for a cruise ship for digital nomads for a very affordable annual fee, accommodation, food and high-quality Wi-Fi satellite supported, allows you to spend a year on a cruise ship travelling the world.  Actually, when you look at the cost it’s very comparable to what you might pay for our rent in central London with food then included.  So is there a world in which you could develop your portfolio executive work style so that actually you spend a year as a digital nomad travelling the world on a cruise ship – make your whole working life like a holiday.   

Maybe you have to be much more established than in your early career, but the possibilities of being a digital nomad become available to you as a portfolio executive in a way which is very difficult to achieve when you are working as a full-time permanent employee.   

One other aspect of holiday and travel, some portfolio executives that I’m working with are looking to work internationally, travel is then paid for as the business expense.  Taking your partner, extending your stay so you have more fun while you’re there, turning a two-day client engagement into a week abroad can really work.  I know that part of my trip to the US Involved a one-day workshop and that one-day workshop then justified booking a significant amount of the travel at expenses to the business.   

  • Can you take advantage of working with overseas clients?   
  • Work with parts of your existing clients, that have overseas departments, to get the business to pay for travel?   

Holidays and travel, you have to plan, you have to take control, you have to decide the choices that work for you.  It’s not good enough just to let stuff happen and for most of the time, you can find a relationship with clients where it’s not necessary for you to be on client site every single week of the year.  You can have a whole new freedom of holiday and travel.   


Charles McLachlan is the founder of FuturePerfect and on a mission to transform the future of work and business. The Portfolio Executive programme is a new initiative to help executives build a sustainable and impactful second-half-career. Creating an alternative future takes imagination, design, organisation and many other thinking skills. Charles is happy to lend them to you.