How can I make the most of my holidays as a Portfolio Executive?

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I meet many, many people who are freelancers or interims or who have moved into the Portfolio Executive workstyle and see themselves as almost self-employed. The mindset of people who are in that time for money business is, every day that I’m not looking for more work or not earning fees, is a cost. It’s a lost opportunity to make money.

Book out your holiday dates

The risk is that you forego many of the benefits of a Portfolio Executive workstyle by not giving the right priority to your holidays.

Most of the Portfolio Executives that I work with have relationships with their clients, where there’s an expectation that they will do a regular amount of activity each month, two or three days per month. In addition, there may be peaks around particular projects. 

My recommendation is that at the beginning of the year you put your holiday dates in your diary.  It may be that you love long weekends. It may be that you want to try and take a month off in August. It may be that you always take three weeks over Christmas, or that you always go skiing in the spring. Whatever it is, put those holidays dates in your diary. Then think of the strategies you can use to maintain your service levels to clients.

There are three tips that I’d offer around maintaining your service level for clients and ensuring you get the holidays that you want.

1 – Manage Expectations

The first thing is to actively manage the expectations of your clients about your capacity to do additional project work. So, let’s say you’re a Finance Director, and your client wants to do a fundraiser, then, because you’ve got your holiday diary set out, you can plan with them when that fundraising can get the most focus from you.

2 – Rhythm of meetings

The second thing I recommend is to look at the regular rhythm of meetings you’ve got with your clients.  Often, you’ll have a schedule of monthly meetings where you’re reviewing with key stakeholders on the progress. Once you’ve got your holiday diary in place, see if you can rearrange some of those meetings, so that they don’t clash with your holiday or set expectation that because you’re on holiday, you won’t be able to come to that particular meeting.

3 – Maintain service level but actually be away

The third thing that I think is worth considering when you look at how you maintain service for your clients through holidays, is to consider whether it’s acceptable for your holiday plans or during some part of your holiday to allocate a small amount of time each day to maintain your service level. This doesn’t mean a big project, but it could mean that in that four-week break that you want to have in August you recognise that, for one or two of those weeks, you might spend an hour a day just checking in, catching up, making sure that things are on the move, and no balls are being dropped.

This is much less of an issue if you are planning to take holidays as extended weekends or 10-day breaks. But the ambition to have a whole month off in August is a worthy one and something that I would certainly see how you can achieve.

Make sure a holiday is really a holiday!

The final thing is not to constantly be half on holiday and half at work. It can be tempting to always have your WhatsApp on and your social media on and your email on and your mobile available. This can mean you are never really be away on holiday.

When you block out your holiday then do make sure that you’ve got an autoresponder on your email that says you’re out of the office.  Do make sure your key stakeholders are aware that you’re on holiday. Put it into your calendar as holiday and if you’ve taken my advice to get somebody who supports your appointments, then they can make sure they manage expectations around that.


So, a great advantage to the Portfolio Executive workstyle is you have much more flexibility about what you do with your time, how much holiday you take and when you take your holiday. But, you’ll only be able to take advantage of that if you’re very intentional about putting the structures and protections in place to ensure that 1) you manage your service level with your clients so you don’t lose them; 2) you don’t make every holiday, a blend between work and holiday and 3) you look at whether for a very long holiday, four weeks plus, you set aside some of the weeks of that holiday where you are providing updates and support for perhaps an hour a day.


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.