Summer is in full swing in the Northern Hemisphere, which means holiday time for many of us.

I'm writing this article during my last working week before taking a four weeks break. Being able to take such a long break in the summer is one reason I moved to solopreneurship at the beginning of 2024¹.

I don't expect everyone to be in the same situation, but ideally, you should take at least a few weeks off during the summer.

Taking such a relatively long break can be either a source of stress or an excellent opportunity for disconnecting, enjoying time with family and friends, cultivating interests, and traveling around.

Whether it's going to be smooth sailing or anxiety-provoking depends mainly on how you're going to prepare for the break.

In today's article, I'm sharing the strategies and tactics I consistently use to ensure I can enjoy my time off with minimal disruption caused by work-related interruptions.

How to prepare your holidays

Here are my seven recommendations to experience a great vacation where you can be fully present with whatever you decide to do without feeling guilty or anxious about what you might be missing out at work.

Many of these recommendations apply to your regular professional life beyond vacation planning, and this is as good a moment to start introducing some discipline in your approach to work.

The first one is a clear example of something you will want to practice regularly.

Capture all your obligations

Many people in the tech sector, especially in leadership positions, have a habit of keeping track of their obligations, tasks, and duties in their minds.

This could be due to different reasons, from a fundamental lack of discipline and habit for tracking things in a written form to the need to look impressive in other people's eyes by showing off their ability to memorize information.

You're a leader who needs to deal with complex topics, not a waiter who needs to memorize a list of items a client ordered for the time it takes them to get the order received in the kitchen.

Plenty of literature and research have proven the nefarious effects of trying to keep track of our obligations and duties in our minds.

David Allen's Getting Things Done² is all about the concept that our brains are great at generating ideas, not storing them. Hence, you need a system you can trust to keep track of all your obligations and open loops outside of your brain.

The Zeigarnik effect³ is a psychological phenomenon that causes our brains to keep memories of unfinished work or tasks. This drains our mental energy, making us less effective in dealing with all those pending tasks. One practice that has been found time and time again to appease the Zeigarnik effect is a very simple one: writing things down⁴.

If you're about to go on a vacation, this is an excellent time to level up your practice of capturing everything. I recommend tracking every task and obligation in your system of choice. I don't care which system you use, as long as you have one and use it consistently.

For ongoing work, make sure you add a summary of where you are, what your thoughts are on the next steps and why, and all the potential open questions you still have not answered.

The more comprehensive you are in your notes, the more you'll allow your brain to trust your ability to pick this work up when you're back without trying to keep its cache warm.

Use delegation as an opportunity to test the team's readiness

The worst thing you can do is to assume that no significant decision will be required while you are out. Things move quickly in our industry, and believing that your organization can wait for you to return can be either naïve or irresponsible.

As you generally want to plan for the worst while hoping for the best, you must delegate responsibilities to your team during your absence.

Oftentimes, what prevents us from delegating more effectively is not people's readiness but our inability to give up control.

Start from the principle that people are not there to sabotage your work. If they do, that's a symptom you have a massive trust problem. Work on that first.

If you've been doing a good job at building trust and alignment within your team, more likely than not, things will work out just fine, and you'll discover that people can make a lot of good decisions when given the right combination of context and autonomy.

Once you return from your break, you will have plenty of time to make adjustments to whatever decision will have been taken during your absence and provide constructive feedback where needed.

This approach is a subset of what we discussed in last week's article about succession planning. If you missed it, you can find it here.

Plan Your Succession Today Sergio Visinoni · Jul 17 Read full story

Over-communicate well in advance

Don't assume people know and will easily remember you will be off. That's especially true for your peers and other C-level leaders in the organization.

Make it a habit to remind people of your upcoming break early and often, and set clear expectations.

Some tactics I've seen working well are the following:

• Update your Slack/Teams status and “display name” with precise information about your being off. I picked this one up while working at Nansen, a fully remote company that relied extensively on written communication to keep the team operating smoothly. As shown in the picture below, I like setting my display name on Slack at least one week before I take off.

• Remind your direct reports multiple times that you'll be entirely off starting from a specific date. Invite them to bring up any topic that requires your input or action well ahead of that date to avoid potential issues. This goes for approving their time off or expenses and critical strategic decisions.

• Reach out to your main peers and stakeholders individually to inform them. Ensure your CFO, the person in charge of HR, or the Marketing Director knows when you will be out. Invite them to bring up any pending topic with you before you take off, and ensure they know who they can rely on during your absence.

In all these situations, make it clear that you are not planning to check in on work-related messages or emails during your absence.

Set clear expectations and avoid ambiguous terminology that we sometimes use to make ourselves look better. Don't forget you're a role model; people will tend to do what you do regardless of what you tell them.

If you want your team members to enjoy their time off, you should start by doing it yourself.

Leave an emergency contact, and stick to it

You can never plan for when things will go really bad; therefore, you want to give people a way to reach out to you when needed. You're still the CTO, and specific decisions will require you to chime in, no matter how much you've been able to delegate proactively during your absence.

I like to instruct people to call or text me on my phone if something important requires attention.

This emergency contact will rarely be used. Reaching someone on their phone is perceived as significantly more intrusive than sending an email or a chat message. People tend to self-regulate and only pull the trigger when they feel it's justified.

Even if nothing major happens, providing people with a way to reach out has a positive effect on two levels:

1. People left “in charge” will feel less anxious knowing they can still rely on you in a significant emergency. This will increase their confidence in dealing with the increased responsibility.

2. Knowing that people will loop you in if something really serious happens will give you the peace of mind of avoiding any proactive check-in from your side. If something terrible happens, someone will call you. There is no need for you to keep scanning your inbox.

In recent years, I have had a couple of situations where someone on my team needed to text or call me while I was out. I was glad they did it in both cases, as we faced severe security-related issues on the platform.

Being pulled in allowed me to help the team by taking some critical decisions that required the person ultimately accountable for them — myself — to be directly involved.

Plan your first day back

On your first day after the break, you don't want to jump straight into action for two reasons: your mind will need time to transition out from the slower and more natural pace of your holidays, and you'll miss a lot of context and information to be up-to-date with the situation.

After a break of two weeks or more, I recommend you block out the entire first day to get yourself up to speed again. I recommend you use that time for two types of activities:

1. Catch up with messages during the first half of the day. You can go through your different inboxes to get a sense of what has happened and capture tasks and topics that require action from your side in our capture system.

2. Have 1-to-1 conversations with key people in your team. Use those conversations to get a summary of what happened during your absence and what they think you should pay attention to.

Here, I want to take an opportunity to give you a pro tip.

What would get you up to speed quickly and effectively after a break?

Ideally, someone who meets with you first thing in the morning and gives you a digest of what you missed, what you should focus on, and what you can safely ignore.

Thirty minutes to one hour of such a debrief could save countless hours catching up with many messages.

While you can achieve part of this through the one-to-one conversations I mentioned above, one thing entirely in your control is doing the same for your manager.

This is something I practice and find very effective.

On the day when your direct manager is back from a break — be it the CEO or someone else — you should leave them a structured and easy-to-digest message with a summary of what happened during their absence, what you think they should focus on or ignore, and an invitation to have a quick call with you if they need any further details.

After all, making your manager's life easier is part of your responsibilities.

Try this out next time, and let me know how it goes.

Plan activities for your off period

Being off doesn't mean being inactive and doing nothing.

It means disconnecting from your profession's daily duties and shifting your focus and attention elsewhere.

As you should know by now, one of my favorite activities is reading good books; there is nothing better than a long vacation to enjoy it even further.

If you are short on recommendations, you can check out some previous articles where I shared reviews of books I read.

📚 Books I read in May 2024 Sergio Visinoni · Jun 12 Read full story

📚 Books I read in June 2024 Sergio Visinoni · Jul 10 Read full story

Reading is just an example of an activity you can perform during your break that can impact or be related to your professional activity while allowing you to be disconnected.

Another example of what I plan to do in the upcoming weeks is the following. I will work about 1,5 hours first thing in the morning daily on the content for an upcoming online course.

I will use this more as a heuristic than a hard rule. It's OK if I miss a morning slot occasionally due to family plans or other reasons, but I'll try to stick with it most days.

By taking this approach, I can make significant progress on something important while avoiding the typical overhead of scheduling, back-and-forth communication, and reactive work.

Take stock of where you are, decide where to go next

Lastly, vacations are a great time to reflect on your situation. From a distance, you can gain clarity on where you are and see the proverbial forest instead of just the trees.

I recommend you take some time to think about where you are in your personal and professional life and where you want to be and figure out if you need to make any significant changes in the upcoming months.

This thinking benefits from long moments of solitude.

I recommend taking long walks, alternating between listening to inspiring podcasts such as Deep Questions⁵, and being alone with yourself and your thoughts.

In my case, these walks are a great source of insights, ideas, and decisions.

Enjoy your time off!

I'll keep posting weekly articles even while I'm off, as I find this activity energizing. I have my morning blocks to progress on these articles without feeling pressured.

I hope some of these posts will help you with your summer break thinking and reflections. If not, you will have quite some material to read after your break!

If you're going on holiday soon, I hope you'll have an excellent time, and I will be happy to welcome you back with more articles after your break.

For those of you who are still around, see you next week!

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