Vacation: A Blessing and a Burden

I thought vacation was a reward! 

On the one hand, vacation can be a beautiful thing. It can provide a mental break from work, and the hustle and bustle of life in running errands and meal preparation and cleaning, enabling us to disconnect a bit, while reconnecting with the activities and people who bring us joy outside of the workplace. 

On the other hand though, even the thought of vacation can cause anxiety for some. Before the time off, we find ourselves scrambling to get everything done, working overtime, and then while gone, we monitor our work email and work texts, dividing our attention, causing issues with those we’re with, and then when we return, we find ourselves inundated with hundreds of emails we couldn’t get to because we were gone. 

I get it, completely. Been there, and done that, and I am still being there and doing that.

When Work Follows You: An Entrepreneur's Experience

My first real extended vacation as an entrepreneur happened in 2024. I was in the midst of working with a new marketing vendor, and we were launching the company’s first marketing campaign. The vendor was new to the marketplace, as was my business, and we were working through logo, branding, and creating the early episodes of the Bonafide Leaders podcast. The idea of leaving my laptop at home seemed foolish and frankly unthinkable. And so, for the first time in several years, the laptop joined me on vacation.

I remember joining a few calls, reviewing and editing podcast episodes and potential social media clips as well as other marketing content that was soon to be released, upon my approval. My family had booked the vacation months in advance, and so the timing of the marketing campaign was not ideal, to say the least. However, I had committed and was looking forward to sharing the time with my family and another family. So, in that week, my attention was divided at times. That experience, while memorable on both the professional and personal side, is not representative of the way I like to do vacation. 

The Myth of Multitasking: Why Presence Matters

As a manager of people for most of my corporate career, I was an advocate of my people taking vacation and leaving their laptops home. One of my core beliefs is that we as people are most effective when we’re present. I had read research and attended a few training classes on the topic, including one with a highly entertaining neuroscientist who clearly dispelled the popular myth that we can successfully multitask. Yes, we can chew gum, talk, walk, or even run, at the same time, but the research and the empirical evidence, prove that we’re both most effective and most happy when isolating our energy on one task at a time.  

As a Fortune 500 executive officer at a dynamic, global, advanced technology company, my beliefs and methods of handling vacation – that is, when gone, be gone – was definitely in the minority, at least amongst my peer group and bosses. There was this tension that I certainly felt in many years in which there was an expectation for me to be available at all times, even during earned vacation periods. Some bosses and peers respected my time off more than others. But, because of the tension, and due to my own growth and maturity, I migrated how I handled vacation over the years.

In the earliest years as an individual contributor, my two- or three-day vacation away from the office was always done at a time in which the business conditions allowed for it. As a financial analyst and accountant, I could pretty much plan my vacation around the financial calendar; monthly close, or the financial planning and budgeting cycle. Timing was straightforward, and I didn’t have many vacation days anyway, so when I took them, I took them in small doses cases and infrequently. 

As I began to earn more vacation time, I also increased my responsibilities at the same time, which created this tug of war internally. “I have the vacation time, so why not use it? But no one else takes four weeks of vacation, so are things going to be okay if I do?” 

As I got into operational leadership roles, no longer was my calendar squarely fixed to the financial calendar. There were now operational and customer demands, which were not nearly as predictable as the financial calendar. And so, in those years, I would take three days here and there, and occasionally a five-day vacation. I struggled with being available for those who needed me at work, while also recognizing the need for my own mental break, and spending some extended quality time with my family. 

Reclaiming My Vacation: A Journey of Delegation

I didn’t like that feeling. Over time, I began envisioning the day when I could vanish from the office without feeling guilt, while also ensuring my absence didn’t cause ripple effects on the business, my peers, and other key stakeholders. I looked into the many approval loops I was on and began investigating what was possible in terms of delegation. Once I discovered how to administer and delegate the control settings and saw that I could do so without creating new risk to the organization, I jumped right in. I also began the process of huddling with key members of my team just ahead of my vacation so that we could review the critical items for disposition, if possible, or assign ongoing items to others on my team. I began advising my boss, and even some peers many days, if not weeks in advance of my upcoming plans to avoid surprises. 

The Art of Letting Go: Empowering Your Team to Lead

The next thing you know, my out of office message was transformed from, “I am out of the office. For immediate assistance, call or text me”, to, “I am out of the office on vacation. If you need assistance in my absence, please contact XYZ for XYZ.” I began the practice of leaving out loud. It was freeing to me and empowering to my teammates. It also demonstrated in a very clear way to my bosses that I was an effective leader, in that I was gone and nothing major ever dropped in my absence. I always left room for my top lieutenants so that if they needed me, I was just a text or phone call away. I rarely heard from them. 

The beauty of empowering others for vacation is that it became a natural thing to do after vacation. My team expected me to lead them, not to micromanage them. My confidence in them helped build their confidence in themselves. It also exposed them to new areas, new networks, decision-making, and governance at a higher level. It was a win-win across the board. 

Is Your Culture Rewarding Rest?

As previously mentioned, there are clearly legitimate times in which work has to join the vacation. And there are other times in which a vacation might need to be rescheduled, be cut short, or reconsidered. I’ve done this and have asked employees of mine to reschedule theirs. Some of those times may include critical deadlines, rapid growth, a major customer issue or deal, among others. 

As leaders, we must ask ourselves some tough questions though. What kind of culture am I creating or have I created? We have to recognize that this vacation thing is much more than just about vacation. On the contrary, it’s about culture. We need to interrogate the messages we’re sending, whether intentionally or unintentionally. Do people take their vacation? Do people enjoy or look forward to their vacation, or are they punished (or just not rewarded) for taking time off? Do people feel compelled to generate their own job security by never turning their work devices off? 

These are legitimate and real questions that we must ask of ourselves because it directly indicates the type of environment and culture that we are creating, sometimes without even knowing it, and the answers to those questions tell an organization or company quite a bit about its culture.

For employers and leaders of people, keep in mind there’s a health element to taking time off. I don’t have space to elaborate on it here, but we shouldn’t take that responsibility to people’s health lightly. 

There are often conflicting realities of taking a vacation, highlighting how what should be a rewarding break can easily become a source of anxiety and a continuation of work. Here, I’ve shared my own struggle of disconnecting fully, while emphasizing the importance of presence and delegation for both individual well-being and team empowerment. Ultimately, an organization's approach to vacation isn't just about time off; it's a direct reflection of its culture, impacting employee health, trust, and effectiveness.

‍