How do you take a whole month off as CEO??

I got an interesting question in response to my last post from a startup CEO, let’s call him “Randy”, that I thought I would publicly answer since it seemed both interesting and important.

“I was intrigued by your [last] post…I am also the CEO of a small startup with eight people under me. I find it incredulous that you are able to take a whole month off in the middle of the year, and not have any consequences. Don’t clients and staff call you all the time?…

…I know I need a break, but there is so much work to do. The team depends so heavily on my direction, that going away for longer than a week (while the rest of my team works) is unthinkable. And it seems to be true of all the other people I know who are in a similar position… On breaks, I take my work on the road with me, or the whole office goes as a group. So its not clear to me how you do it, and in some ways makes me question the nature of your work…”

Randy, you have a great point, and let me try to answer your queries!

Before I begin, please understand that taking any time off beyond a couple of days takes immense preparation, as you will see. So impulsive trips (unless emergencies) simply don’t happen.

That said, here’s how I do it:

  • Establish strong communication and teamwork in your company: For anyone to take time off, its really important that your team is strong and communicating with each other. As I said in my last post, it became very obvious that this was an issue at Month #8, so I set about fixing that. Now its critical that every person has two people to cover them at any given time, which means that people can take leave at any given time.
  • Block out your dates a minimum of 3-6 months in advance, after talking to your team: Taking a month off (actually any time off longer than a couple of days) takes immense amounts of preparation. You need to mentally prepare your team for it, and you need to be mentally and emotionally committed to sticking to those dates. First, once I’ve figured out a period that I think will work, I usually talk to my immediate support team to see if there are significant conflicts or issues that I may have missed. If they don’t see any, I then speak to the investors/Board/owners, and once they approve (which they usually do because the rest of my support team is on board), I block the dates off immediately in the company calendar. Its very important to do this because it starts the process of clearly demarcating that time for yourself. Often people are much more forgiving of your departure because they have known for so long.
  • Involve your team in the decision making; explain your thinking: While the owners know why, I had to explain to my team and the wider company why I needed to take time off. In the beginning, not everyone agreed, or understood, or was on-board. However, the most important people (my immediate support team), being the good people they are (and seeing how worn out and exhausted I was), got it…which mattered most. The rest of the company was much more supportive after the first time I took a break. They saw the difference in my energy levels, the freshness of my thinking, and how it trickled down to them personally and professionally, so it became easier for them to support my sojourn the second time.  More importantly, they realized that they weren’t abandoned and had no reason to panic.
  • Develop a contingency plan that is internally shared, train your team, and remind them constantly: Make sure you develop a contingency plan for your duties so that your team will know when and how to back you up, and start training them well in advance. Make a clear outline of your duties and then delegate each of these to your support team members. Then pass this information out to the whole office. Remind them constantly that you will be out-of-town.

In my case, I met with my support team first to ensure they were comfortable with the new responsibilities. They were often trained months in advance and I even sent staff over to test out their respective capabilities as back-ups. It forced them to pick up new skillsets and capabilities. I also met with my team AS A TEAM, so they always knew what the other was doing. Communication is absolutely key. A month or two before my departure, I announced the information at our firm-wide meeting, and opened it up for questions, comments, or concerns from everyone.

  • Plan your work out in advance so that you or your team aren’t overly overwhelmed: Your team is likely already stressed out about your departure, so don’t make it worse for them. Plan your work well ahead so that they aren’t hit with a brick wall when you depart.

For example, in my case, recruiting (particularly the interviewing and decision-making) was one aspect of work that I could NOT delegate to anyone in my team – they simply lacked the capability and confidence to do it correctly. So I took it off their plate completely and worked around it. Three months ahead, I got a clear idea of what HR needs existed in the office. I then paced myself to ensure that these were met prior to my departure. And I spoke constantly to the whole office to bring HR needs to the front as soon as they emerged so that they could be resolved before I left. Amazingly it worked, and while I was gone, people were so busy adjusting to the new people and work, that I barely heard a peep from anyone.

  • Keep your team busy with clear deliverables on your return, and hold them accountable: I’ve generally found that people create more drama when they don’t have enough work on their plates, and nothing to aim for. Prior to my departure, I ensure that everyone in the company has clear deliverables and targets that I will need to be updated upon my return. This has been magic in terms of not being bothered. Even if I end up extending by a couple of days, it usually is fine because people are thrilled with the extra time. Upon my return, I immediately followed up and ensured that things were done to my satisfaction. Essentially they were held accountable.

There are about 30-50 staff members in my company on any given day (the swell depends on interns and part-timers who work only certain days of the week or month). I am generally clear about the nature of my output and  while I am the “CEO” or “Managing Director”, my work is primarily administrative in nature. I have a number of people who can back me up and hold the fort in the case of an emergency. On the design side, which is our ultimate “product”, I do very little. This was designed around my skillset, the type of talent pool we had access to, and how best I could add value to the company. I could and did hire lots of good people who do excellent design, took most things non-design off their plates, and put that on the plates of people like myself, and a few others who could handle it. For now, this works brilliantly. And this is how I do it ūüôā

Hope this answers your question.

Why I take a month-long break every year, while the rest of the company works

Taking a break to contemplate life and your place in it, along with your work can greatly benefit you and your company (photocredit:

The more recent pause in posts has been because I took a four-week break from work and headed home to the US where I am from. I hadn’t seen my family in a year and missed them horribly. This “long break” was a clause that I had negotiated with the owners when they brought me on board (they offered me a low salary, so I needed other perks to make up for it): I needed a month off every year (unpaid), even while the company worked. Some people would say that it is both selfish and stupid, but for the company and myself (both as a leader¬†and as a person), it has been invaluable.

Here’s how both I and the company have benefitted¬†on the personal side:

  • It rewards and refreshes the mind, body and soul in a VERY necessary way: Good leadership is ultimately backbreaking servitude. My hours are long and, often, thankless, and leadership is extraordinarily lonely. This is not by choice.¬†It just comes with the job (not asking¬†for pity…I signed up knowingly). As you go up the chain-of-command in a company, you have fewer and fewer peers whom you can talk to and confide in. Many things are confidential, and you deal with much more “heavy” material – cases that no one else wants to touch, things that no one wants to (or can)¬†take responsibility for, and in many cases, jobs that require a skillset that¬†only you might have. This eats into your energy and time in a way I can’t express. Without a family or support system at home (or in the office) to balance things out, it slowly eats away at your system. This is why most CEOs are compensated so highly (sometimes I think its a bit much and unnecessary).¬†I think its so that they can have the other perks to balance out the heat of the job. In my case, I get none of those perks, including pay. And I have no family and few¬†friends (partially because the hours are so long and partially because I don’t really fit in here). My burnout rate is consequently, very high.¬†These breaks keep me healthy, and consequently the company healthy and on the right path.
  • Mental and Emotional Rejuvenation Fuel Necessary Depth of Thought: The reason I need such a long break is because I need to be charged up physically, mentally, and emotionally. It usually takes a week for me to get physically recharged (mostly with good food and sleep); but it takes longer to get mentally and emotionally recharged. When the brain tires, creativity declines, and my greatest asset in my current position is to be creative when everyone else is not; and in a capacity that other people cannot be. As CEO, I am responsible for strategic planning and execution, overall problem analysis, goal orientation and direction. I have to both think out the goals at a company, department and individual level, and then figure out a way to get there, and then motivate my team to move in that direction. If they don’t see it, its my fault. If the company or department or individual is stuck, its ultimately my job to find a solution (either through or outside my team) and then move towards executing it. This is not physical strength, but mental and emotional strength, and this is what fuels creativity and depth of thought.

The break, for example, is what fueled the space to collect and write down my thoughts, and start blogging again. Similar to a cow chewing the cud, the break allowed for a lot of things that I had mentally filed away when I was triaging a specific case to come back and sift through. I am able to see things much clearer as a result…things¬†that were done right or wrong, things that needed to be fixed or done better, holes that are still left and leaking within the company. It all comes back in moments of quiet, and it allows tremendous depth of thought and much more efficient action. I grow a lot in those moments, as does my skillset, and this makes the whole company grow¬†as a result. My brain floods with ideas; problems I have long been contemplating suddenly have solutions. Its really exciting, and counterintuitive, but I often find I do my greatest work when I am on “holiday.” And its because I’m allowed the space to think deeply.

Here’s why on the company side:

  • It builds resilience in the firm: As the ultimate servant, people can get a little too dependent on you to do things that they can probably do themselves.¬†So when I’m gone and my contact with them is curbed, it forces them to grow and step up in ways they haven’t before. I often come back to see depth of thought on the part of many members of my team, lots more questions and answers, eagerness to learn and grow, and greater levels of confidence. Its a beautiful thing to see.
  • Performance is glaringly obvious: Conversely, I’m also able to see the “holes” in my team, company strategy or structure, communication, etc. Based on this, I know how well we have been performing, how much more I can push my team and the company. At an individual level, I can see who all have grown as individuals or team players, and who haven’t…who fit in the company and who don’t. Everything becomes much more obvious.

This time, for example, I knew that we were doing good as a team, and company when I got back, and it was incredibly affirming.

Last year (eight months after I took over as CEO) when I got back from my break, I had a long line of people (juniors, seniors, and upper management, including the owners) waiting with a list of complaints of things to fix. I could see that while we had made a lot of progress in the first eight months, there were still LOTS of things to do. Had it not been for the break, I probably would have been overwhelmed and unable to sieve through the chaos. But it was soon glaringly obvious to me that there were still LOTS of HR issues. Communication and team-building, as well as the need for mature design leadership emerged as the key problems that I needed to solve. These became my priorities, and I only realized the results when I came back this time.

In contrast to last year, when I got back this year, the line of people to see me were mostly seniors (not the juniors or upper management as last year) and their lists were mostly happy/proud updating, and any key resources or things they needed from me in order to move forward. I could see that they had thought deeper about things, stepped up better, and that the team was MUCH stronger. Confidence levels were higher. Work was moving forward at a rapid pace. Most people were communicating and resolving differences between themselves. It was quite affirming…I knew we had done good over the past year, and it was time to move forward with the next phase of growth…time for me to step up yet again.

For those who ask how things had changed in the first eight months, and how I gauged progress there, here’s something for you. When I first got there at Month #1, only the owners showed up with a long list of complaints of things to fix. No one else wanted to talk to me or have anything to do with me. It took me several months to¬†gain everyone’s trust and get them highlighting their biggest issues. The issues were at a fundamental, extremely critical level…there¬†was a lack of vision, mission, core values, goals, and a complete lack of accountability; which I immediately set about fixing and implementing before I went on break. So the fact that everyone¬†showed up to complain to me with a long list, was in and of itself a big achievement and showcased trust.¬†Their complaints had also¬†shifted from fundamental issues with the company¬†to¬†team-related¬†issues they had with each other – ¬†a HUGE shift (you want complaints to move from being heavily substantive to more trivial issues). Hence I knew we had progressed, but there was still great chaos in other respects.

In conclusion, I think these breaks are invaluable in multiple ways, and hopefully you might take this to heart in terms of your own productivity and that of the company’s.

And this is why I will hopefully continue to take long breaks while my company works.

Where the heck have I been?

I know I’ve been very quiet on the blogging front, and I take full responsibility for this.

Not to make excuses, but I’ve just been insanely busy. Since January 2013, I’ve taken over the helm of a 20-year old¬†boutique architecture firm in Singapore. This was done as a result of my passion for learning about design, really testing my theories of entrepreneurship, and having an impact on the language of sustainability and infrastructure development in Asia.¬†Even though the firm has done extraordinary work over the years and has been a pioneer in design, architecture and landscape architecture, it seemed like it had lost its way, and like SO many architecture firms, had been badly managed for several years.¬†Turning around an established company in an economy that is changing as fast as Singapore’s and Asia’s (where most of our clients are based), is NOT easy, and has taken an obscene number of hours of effort, energy and time.


I spend so much time talking to people and on the computer, on email, writing reports and memos and doing powerpoints all day long, that the last thing I want to do is sit on a computer for longer after a LONG day and type some more. I’ve started to compose so many different posts only to¬†wake up two hours later, with a sore neck, a sleeping computer¬†on my lap and three words on my post. Not surprisingly, two minutes later, I’m completely supine as is the computer, with three words still on the post. The next day, new thoughts come in and I do the same ritual everyday. Then I just gave up.

But in late July 2014, I realized that I HAD to make more of an effort. Too many lessons were being forgotten. I had stopped journaling and blogging, and it was affecting the clarity of my own thinking. So here I am, making another feeble attempt. I hope I do better this time!