The Challenges of Moving versus Traveling

I’m in the midst of moving house here in SG. Even though this is my fourth time in four years, and I actually have lots of help this time (none in the past), I am not looking forward to it. For one, I love where I’m staying now, and am unsure about the level of comfort in my next place, and I’m also a little weary from the moves. Maybe its age…

That said, I’m still an avid (well, kinda outta practice) backpacker and low budget traveler, and have been so for the past 15 years. Often a single pack can last me through six (6)-nine (9) months…so why is a single move harder than an eternal move (backpacking)?

I thought about that for a while too, and after some rumination, I came up with the following:

  • Backpacking requires very little stuff, Being a CEO in Asia needs lots of nice stuff: When I first got to Singapore, I had 1.5 suitcases of stuff…and it covered everything from clothes and shoes to linens. However, it quickly became obvious that it simply wouldn’t do…I needed more clothes and stuff. For example, my backpacker sandals (keen newports) and flipflops were simply not enough anymore. I needed more grown up shoes, and clothes, and perfume, and grooming products that I had never cared to have before. The result is an extra suitcase of clothes and shoes.


  • Backpackers have flexible schedules; Full time workers don’t and live on a good night’s sleep: In my capacity as a full-time worker and CEO, I  absolutely need a good night’s sleep. For 2.5 years, I survived on the mattresses that were provided to me wherever I went (similar to when I traveled), but my sleep was disturbed and I had frequent backaches, and I never had the schedule to allow me to sleep in. When I finally took as CEO, my reliability and availability in the office was NOT negotiable. I finally bit the bullet and bought a bed. So now I lug a queen-size bed around, as opposed to a sleeping bag and a pad, with every move. And with it come sheets, pillows and comfortable linens. You get the picture.


  • Backpackers can chill out in their eating timing, places and food types; Full-time workers need disciplined eating: In most of the places I lived in or passed through in the past, I could survive on anything that was provided to me so long as it was vegetarian. I rarely stayed too long in a place, so even if the food wasn’t great there, you could move on to a place where the food might be better, or atleast your options were different. As a full-time worker, you are more settled, you can’t afford to get sick from what you eat, and you have to maintain a schedule and discipline in your eating to be effective at work and in life. More than anything else, this lesson took me the LONGEST time to learn and come to terms with. But once I did, my health improved dramatically. This also translated into needing to lug around a whole heap of things I didn’t care to before…cups, plates, mugs, utensils, pots/pans, spices, ingredients…you name it! And you had to buy things in sets because you had the added pressure of entertaining. Now I have atleast 2-3 boxes of kitchen ware.

That’s how after four years, I have gone from 1.5 suitcases to 4 suitcases, 2 boxes, and a bed!!

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 🙂

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.

The Bargaining Power of a Good Employee

What has become extremely obvious to me in the position of CEO, is that I spend a heck of a lot of time on HR. We don’t have a dedicated HR person, which might have something to do with it, but I do believe that a LOT of being a CEO is knowing your people well, and working closely with them to make the magic happen in the office. That’s generally the role of any manager, but as CEO, you are the ultimate manager (or ultimate servant, depending on how you see it).

Here’s a secret that most employees don’t understand. If you are a really good employee, most employers will do just about anything (within reason) to keep you.

Good employees have incredible bargaining power, so long as they stay in reason and know their worth. (credit: BusinessInsider)

What constitutes a “good employee”?? Simple…have a good attitude and fulfill the mandates of your role really well (become indispensable to your company in your role). What makes you negotiable is knowing your worth and being reasonable within that. The key is again, to be reasonable. I know too many employees who get ahead of themselves, think they are more important than they really are, make the employer dance to their tunes, and then are shocked when the employer pulls out. No one (not even Steve Jobs!) is that invaluable to a company. Know your worth and stay within reason. 

White House CTO, Todd Park (image credit:

Todd Park, CTO of the White House (a new job in and of itself), showed that recently. Even he needed to walk away from a dream job that was literally changing and having a huge impact on the world. Rumor has it that his wife supposedly gave him an ultimatum – family (in Silicon Valley) or job (in DC). He chose family, and walked away. But he was such a good employee, that even the President of the United States worked around his needs. So now for the first time ever, the CTO will be working from Silicon Valley. Does this mean even the White House will have tele-commuters? How will this change the future of our governing officers? Definitely something to think about…but the key again is that good employees often have a lot more power than they think they do.

Two of the Most Important and Undervalued Skills for Success in the Workplace

Reading Constantly and Writing Well are by far the most important skills in the workplace for success.

A few days ago, I was giving my team a much-needed lecture on the importance of constantly reading and staying abreast of trends, as well as improving upon their writing skills. In Asia, where a liberal arts education is virtually unknown, few people have proper reading or writing skills. One might easily fault the language issue…and to be honest, I can be very forgiving of people from countries who were never exposed to English. Still, I don’t think that’s an excuse for NOT reading and keeping up with the latest trends, even in your own language, improving your writing and diction in your own language. That said, even of the Asian countries with easily available English educations, and former British (or American) colonies , I find the South Asian countries (India, Nepal, Bhutan, Pakistan and Sri Lanka) churn out people FAR better at speaking, reading, and writing in whatever language, including English (of course, English is the only language I can really judge in, but I can extrapolate that to a general interest in writing as well). I’m honestly not sure why that is, but that’s a different story!

Why is reading and writing so important?? Well, they are the basis for communication, and communication is the basis for ALL business and work, generally. If you aren’t keeping up with the latest trends and reading constantly, you will soon become irrelevant; and, if you can’t write, you can forget getting very far in any aspect of your professional development.

Read constantly. Keep up with the trends in your industry. It is the only thing that will keep you sharp and growing at a rapid rate. This is a necessary key to success in the workplace, because to mentor and grow, you need to stay ahead of the people who surround you. Don’t believe me? Read this article about Warren Buffett’s success formula, and this one from HBR.

Write well – clearly and concisely. Today I was reading this post about Jeff Bezos’ leadership style. A trained engineer (like me), I was impressed by his emphasis on writing. To be honest, I find writing to be an extraordinarily important skill. It is the fundamental for all success in the workplace…documentation, letters, communication all involve writing, and without it, you can forget getting very far. How you write is how people will connect with you; how they will perceive you; its where all your speech starts, and your thought ends. And I find that clarity of writing correlates heavily with clarity of thought. If you write clearly, it means you are thinking clearly. And how do you write well? Start with reading…the more you read, the better you will write…

Steve Jobs: The Art of Taking an Insult and Making Some Fans

Whenever you stick your neck out and do something differently, you are going to have people pissed off at you…sometimes pretty badly. Over the years, I’ve had my fair share of the same. Change is always disruptive and hard, and sometimes, the more effective or efficient you are, the more disruptive it is (this is true of both change for the good or bad). The insults, consequently, are proportionally bad and hard. Its taken me some time to learn how to deal with insults, and I’m constantly seeking new ways to understand the art of dealing with them.

Today’s lesson is from Steve Jobs, ironically a great insulter himself, who shows us the art of turning an “ouch” into an enthused ovation.

1.  Show your insulter and the audience some respect (if they deserve it). In this case, it took guts to stand up and question a respected figure. Steve did not put him down in any way, nor did he turn the audience against him. There was no laughing at him or belligerence or defensiveness. It was respectful throughout.

2. Pause and take your time. Steve takes his time answering. This is good for several reasons. It allows you to calm yourself down, collect your thoughts and answer in a coherent and controlled manner.  Essentially, it takes power away from the insulter and gives it back to you.

3. Separate out the personal/emotional and focus on the core problem the insulter has. While the question started out and ended personally (“you don’t know what you are talking about” and “maybe you can tell us what you’ve been doing for seven years!!”), it became very pointed and clear what specifically the insulter had a problem with was Java, and probably the fact that he didn’t understand Steve’s methods and direction. Steve honed into this and focused his response on that.

4. Use humor without making it personal. After pausing, Steve starts in a light-hearted manner and keeps infusing humor where he can. Humor always diffuses tension. It was never, however, personal. Again, it sets the whole group at ease, including the insulter.

5.  If your insulter is right, say so. This goes back to point #1, of showing respect. The audience isn’t stupid either and they know that the insulter had a point. Steve gains everyone’s respect by admitting that he was right in parts.

6. Turn the insult into an opportunity to sell/explain your point-of-view: Often insults get the most attention…audience members who have may have tuned out, tune back in. You could’ve heard a pin-drop in that pause between insult and response. Steve,  a genius at captivating an audience, capitalized on that opportunity. In this case, he talks about how he starts with the audience in mind, not the technology, and how that dictates his entire philosophy and helps ultimately sell apple products. He then tells stories and keeps the audience engaged. Essentially, he turned an insult into a powerful 5 min story-telling session that showcased the hardworking team at Apple.

7. Apologize, if there is reason to. Steve does this multiple times, and he is clear what is both sorry for, and what he isn’t.

8. Summarize and finish strong. In the last 10 seconds, Steve sums it up very quickly, ensuring his last words leave the audience in his court…i.e. “support my team who are kicking some serious butt.”

Interestingly, I googled “the art of taking an insult”, and the top search results all linked to “the art of giving an insult.” It should say something about our priorities!! 🙂

Other points of view: Zen and the Art of Dealing with Insults