Entrepreneurship Lesson #322: On Asking for Forgiveness, Rather than Permission

When you are growing up as a child, parents often try to reinforce the concept of permission. If you want something, you have to ask for it – politely. Only then, can you  actually get it.

The idea of good manners certainly makes sense when you’re a young child. But could it be that it’s actually preventing our progress later on in life – especially in the world of startups, when you’re trying to create something new or go against status quo?

Asking for Forgiveness, Rather than Permission

As we enter adult life, we come face-to-face with many layers of bureaucracy in the world. Especially, in the workplace, whether it’s within our own company, where we need to get permission from 3 different layers of management or with the people on the outside. We are conditioned to think that if we want something, we need to have somebody give us permission to do so.

However, working in a fast-paced startup environment begins to shift your mindset. More often than not, asking for permission just doesn’t get you anywhere. In the best case scenario, it leads to numerous delays. In the worst case scenario, if your request is just a little out of the ordinary, people will have a tendency to reject it by auto-pilot instead of taking the time to entertain it.

When working at Kiva.org – the world’s faster growing online non-profit – I really learned how this point is driven home . Their idea of enabling citizens in the developed countries to sponsor small entrepreneurs in the developing world was so outside the framework of anything else that existed at that time, that they had no precedent to follow and certainly nobody that would “give them official permission to proceed”.

They spent a significant chunk of time trying to get an answer from the SEC on whether they could move forward with their venture and nobody could give them a straight answer. Until one day that just decided to go for it and deal with the consequences later.

They ultimately did.

Although their path was not without challenges, if they waited for somebody to give them permission to operate, they may still have not launched. Or worse yet, somebody would’ve told them no.

What ended up happening in that situation – and in many others – when you just go through and it, the consequences are often less dramatic and long-lasting than you expect. Even if you get in trouble, the chances are that things will find a way of working out. And if you succeed with what you set out to do, you’ll find that a lot of the initial resistance and bureaucracy begins disappear, as people begin to believe more in your idea.

Ultimately, if you truly want to achieve something and believe that this is the right thing to do, you simply can’t afford to sit on the sidelines until someone “lets” you do it. Give yourself permission and go for it.

Entrepreneurship Lesson #321: On The Importance of Sitting Together

At the time when I ran a publishing startup, our first office was a small 200-square feet place, on the 2nd floor of a bank branch, c0nsisting of one irregular shaped room. We started off with just 3 people and the space felt a little tight. So you can imagine what it was like when we expanded to 6 – and used it for storing thousands of copies of the magazine that we published every quarter.

That said, there was something really productive about all of us working out of the same open (albeit slightly claustrophobic) space. The fact that there was no walls made collaboration easier and made it really easy to resolve issues quickly and work on team tasks effectively. After all, if there was any problems, all we had to do was turn the chair around and we could resolve it right away.

Eventually when we moved to a larger space consisting of 2 separate rooms, we had to divide up the staff and the effect was immediate. Interaction among people sitting in one room vs. people sitting in the other decreased immensely. You bonded with the people closer to you and grew apart from people in the other room – even though they were less than 50 feet away.

I would take it even step further now. In the currently startup, we have a similar environment where there is just have one giant open area with many tables strewn about (there are multiple startups working out of this incubator). That works very well. In our case, we have 4 tables put together and people sitting around them, facing one another. Amazingly enough, you can even see the same effect on a micro-scale with the people who sit next to each other. There is more interaction going on among those who sit side by side, rather than across the table.

Perhaps some of that is self-selected – we put people with common responsibilities closer to one another. But I believe  it goes beyond that. It’s the little things that begin adding up – whether it’s sharing and discussing a latest article or showing the person next to you an email you want their opinion on – without even noticing, these things end up bringing you closer together professionally.

Maybe this is where the “right-hand man” expression is coming from…

Your Future – 3 Years at a Time

Where do you see yourself in 10 years? You’ve probably heard this question come up in job interviews. Or perhaps you’ve been asked – what do you want to do for the rest of your life?

Personally, I always found it very hard to answer these questions. I wonder how accurately can we really predict a 10-year timeframe. When we were 15, did we know everything that would happen to us leading up to our 25 year birthday? Did we anticipate how our interests would change and evolve and all the new things and experiences we’d come across?

Some people know when they are 4 that they want to be a doctor or an astronaut or anybody in between. For the rest of us, the path is less set in stone. Over time, for most of us, life took a series of unexpected turns, we gained new perspectives, our work and family situations may have changed, and we generally started to look at the world differently.

Daniel Gilbert, the author of a book called Stumbling on Happiness, claims that generally, we are pretty poor predictors of what will make us happy in the future. His reasoning is that our imagination fails to realize how things will feel when they actually occur and that the longer the timeframe is, the more likely we’ll be wrong.

In other words, if you try to visualize yourself 15 years from now, where you live, how you feel, and so on – it will be most likely inaccurate (and, surprisingly, can be quite similar to your existing situation).

We can see this happening all around us – people make decisions that they ultimately end up unhappy with. I’ve been around a lot of folks that have gone to study Finance because they were attracted to the prospect of making $100,000 per year. It takes many of them a couple of years to realize that this money doesn’t really matter that much because they are unfulfilled in their personal life and have no time for anything else.

What went wrong? We failed to predict and anticipate what will make us happy down the line.

The 3-Year Timeframe

So, if you can’t accurately predict yourself in 10 years, how should you plan ahead? We still need to setup goals and a general sense direction for ourselves, right?

Yes, we do. We certainly need to better understand in general what kind of things make us happy, but it’s also important to keep in mind that these things change as we change. Having a desire to travel the world today may take a backseat to raising your family when you get your first child.

While not perfect, I try to build my plans and goals around a 3 year term (could be 2, could be 4 – depends on you). Anything longer and I don’t think I can predict what will really be going on then.

Three years is short enough for you to be able to visualize where you’ll end up, but it is long enough to make some real achievements in the meantime.

This is particularly pertinent when you’re thinking about your work opportunities. As I’m writing this, I have an interesting job opportunity with a startup organization on the table that I’m considering taking. It’s great in terms of getting involved in an exciting and different project, playing a key role with the company, and making a contribution to the society.

However, deep down, I know that I want to return to running my own company a couple of years down the line. So, being able to project this in 2-3 year terms and making a conscious decision that after this term, I will re-evaluate my direction makes it a lot easier to commit to this.

There will be, no doubt, people that will be skeptical of approaching this from a 3 year goal perspective. Some may say that you’re jumping around too much from one thing to another without becoming specialized in any. Others may feel that it’s too much work if you try to change your line of work so frequently.

That’s fine. This is not for everybody. Rather, this is for those who are still not entirely sure what they want to ultimately do in their lives and those that want to experience as much as possible by trying themselves in different roles. It’s simply about giving yourself a permission to realize that it’s OK to change directions after a few years.

The Unexpected Danger of Volunteering in the Developing World

In 2009, I’ve spent 7 seven months volunteering in Asia. The experience was very interesting on many levels, so this year, I was thinking of going somewhere again for a couple of weeks or a month to volunteer on some other projects.

Over the last few years, there have been a number of companies that popped up that specialize in voluntourism – where instead of lying on the beach in the Bahamas, you can choose to spend your vacation in the developing world working on some volunteer project.

I started looking into it, but couldn’t shake the nagging feeling that something was wrong with the concept of short-term volunteering in the developing world.

Why Do People LIKE To Volunteer in the Developing World

Thinking back about my own time in Central Asia and in India, as well as the experience of many other people who did something similar, one thought kept crossing my mind.

It was really a good experience for us to volunteer there.

On one level, it satisfies our internal ego and wanting to perceive ourselves as doing good for the world. Whether or no, we really made a sizable contribution, it felt that we were making a difference.

As a Western volunteer in a place like Africa, Asia, South America, etc. – you get a lot of attention. Depending on where you are (i.e. living in a small village or a community), you even become your own pseudo-celebrity, where everybody wants to talk to you, be your friend, offer you meals, and so on. Because you stand out and are perceived as a Westerner, you get treated very well. And compared to back home, where you could be an average Joe or Jill, that feels good.

And lastly, although you are living in a developing country, in conditions that are likely way below your typical level of comfort, deep down, you know that this is only temporary. You may not have running water or electricity for the time being, but you are able to comfort yourself with the thought that in a couple of weeks, you’ll be going back home to your regular comforts. As such, it feels more like an adventure or a “discovery” – which just adds to the overall experience.

So, what can I do?

The purpose of this article is not to turn people off from volunteering, but rather to get them to re-evaluate the reasons they are doing it and their expectations.

- Don’t approach this as if you’re a white knight coming to an impoverished community to save them. The reality is that your contribution will likely be quite small – not insignificant, but small nevertheless.

- Make the commitment to do the work. Some of the voluntourism programs offer you to travel there, work 2-3 hours a day, and then spend the rest of the time on excursions and relaxations. I think that undermines the whole purpose. If you want to travel and relax, travel and relax. If you want to volunteer, commit to it fully, make it the focal point of the trip and make the most of your time there.

- Understand the reasons why you’re doing it. To some people, it will be the desire to see another culture and learn something about themselves and others. To others, it will be to satisfy their internal ego and desire to make a difference. Whatever the reason is – be honest with yourself and what you want to get out of it.

- Turn it into a longer trip, if possible. Your impact will grow exponentially the more time you spend there. Keep in mind that it will take a few weeks just to get settled in, understand the project, get to know people and establish trust from the locals. To really connect with the community, you need to give yourself time.

- Consider what skills you can bring. Granted, if you are a doctor or an engineer and you’re going there, you will be able to contribute significantly more, as your skills would be very valued there. But whatever your strong points are, make sure that you’re able to give something – rather than ending up a drain on the resources of the host organization.

To conclude this, I have to admit that I am just as guilty of most of these elements. When I started to volunteer, I had a lot of misconceptions over what it will be like, what I’ll be able to accomplish, and what impact I’ll be able to make.

But at the end of the day, we have to be honest with ourselves – do we really want to go and make a difference or do we just want to feel better about ourselves and have a good story to tell?

Unemployed? Making the most of 9 to 5!

You never really realize what being unemployed truly feels like, until you find yourself in this situation. Although I strongly believe in not making excuses for it, I do have to admit that it can be challenging.

Prior to that, you think that when you suddenly have all of that free time, you are able to accomplish all of the things you’ve wanted to but never had the time. The actual reality turns out to be quite different.  Instead of fixing up the house, going to travel for a bit, or learning a new skill – you can often end up in this hazy state where days go by and mold into one another.

The whole process can end up being quite demoralizing – it’s no coincidence that the depression is also on the rise nationwide. We often tend to attach our sense of identity to the type of work that we do, so when we become unemployed, our levels of confidence and self-worth end up going down as well.

The most challenging part of it all can be making the most of your time while you are looking for work. It’s often difficult to enjoy yourself at any activity, because you always have that little voice in the back of your mind saying that: “maybe you should be looking for work right now?” or “should you really be relaxing right now while you’re not bringing an income.”

But let’s face the facts. Looking for work doesn’t take up 8 hours a day (typically). Unemployment can last for a pretty long time. Feeling guilty doesn’t get you anywhere.

So, what can you do to turn the situation around a bit? Everybody probably has their own advice to offer, but here are a few things that work for me:

- Focus on things that you DO have control over, such as your health and fitness.

When you’re unemployed, it often feels that you’ve lost the control over your own destiny and that ends up spilling over in other parts of your life.

It’s important to realize that you are still in control of many things – your health being one of them. You may not be able to control your job, but you can focus on starting an exercise routine and better eating habits.

I’ve been doing some jogging on and off for a while before. However, I decided to sign up for a half-marathon three months in advance and to begin training daily for it.

This turned out to be very helpful on several levels. For one, that hour and a half a day of running and exercising gets your mind off things and leaves you feeling great afterwards.

Secondly, having a specific goal forced me to really commit to training on a daily basis. It gives a purpose and it keeps me accountable.

Whatever exercice regimen you set for yourself, make sure to be clear about your goals and work on a week-by-week plan on getting there.

- Use the free time to try new activities and make sure to get out of the house. Meetup.com is great for that.

This is an often-repeated advice and may sound a bit like a cliche, but I believe that it’s truly important to your own well-being to get out of the house on a regular basis and do things with other people.

It keeps you active, improves your confidence as you meet others in a similar situation, and even develops your interests and hobbies further.

For myself, I’ve joined meetup.com and ended up in a couple of great groups. Among them, I usually end up attending 1 or 2 events per week, ranging from hiking and cycling to just playing ping-pong or meeting up in a cafe.

In fact, I liked it to much that I started my own group focused around outdoor recreation.This also forces me to focus and plan my free time better.

- Consider volunteering. We are happier when we give back.

People often find that they are most fulfilled when they do work that benefits others. Even if you don’t have a paying job right now, it doesn’t mean that you can’t contribute to others. Volunteering is a good way to start with a small time commitment and you can often be surprised at just what kind of opportunities you may have available to you.

For example, in the past, I’ve spent a few years volunteering as a Night Disaster Responder for the American Red Cross. Not only I was able to pick up valuable skills, like First Aid, Shelter Operations, Mass Care, and so on – but it was also an opportunity to do something that I could never do otherwise – responding to fires, floods, and other disasters in New York City.

- Limit TV consumption.

This may be a tough one for many. When there is a lot of downtime, we are often drawn to the TV as a way to pass the time and forget about the troubles of reality. However, I think that many find that if they spend 3-4 hours watching television, they come out feeling even worse than they did beforehand. It has a power to suck your energy out of you.

I would highly recommend to limit the amount of time you spend on TV and when you do, sit down with a specific goal in mind (ie. watch a specific movie rather than 4 hours of day time television). Better yet, go and spend that time outside, read a book, or engage in physical activities – you will certainly feel better afterwards.

- Create a schedule for your days and goals for your months.

It can be a terrible feeling to realize that yet another month has gone by and you haven’t really accomplished anything since then.

In order to avoid that, you need to create some structure to your day – even if it’s all self-made. It can be challenging when you don’t have any specific commitments or things that absolutely have to complete during the day.

But even then, you can still plan your days. To give you an example, I aim to wake up same time every morning and sit down to write out the activities for the day. It usually includes 3-4 hours of job hunting, an a hour and a half for exercising and running, another hour or two for working on miscellaneous projects and the rest of the time on various household chores. This helps you avoid the feeling that the whole day has gone by and you didn’t get to do anything.

On a more long-term scale, you also want to sit down and consciously think about what you’d like to accomplish over the course of this month and the next one. If you don’t set up these goals, you should not be surprised when the month goes by and nothing gets accomplished.

Although far from perfect, here’s an example of my own:

- Running – get up to 30 miles per week (increase slightly each month)

- Outdoor Recreation – organize two trips per month into the outdoors (hiking, etc.)

- Blog – write at least 1 blog post per week

- Time Management – wake up by 7.45am every morning.

- Dancing – learn how to swing dance within 3 months by taking at least 1 lesson per week

You get the point.

The fact of the matter is that having these goals – whether it’s swing dancing or getting outdoors – keeps you straight and gives you an opportunity to focus on what you can do during the time of unemployment.

Don’t lose this time. You won’t have a chance to get it back.

Making a Choice, Any Choice

When I was in the process of selling my business, I’ve heard and read about many other business owners who went through a very rough time after they sold it. The reason being that so much of their time and energy has been invested into their business that they’ve began to tie their own identity to it. So, when it was no longer their company to run, they were at a loss as to what to do next.

I thought that this was a pretty realistic thing that can happen, but figured that it would be different for me. I was young, was already pretty burned out from the business, and was looking forward to moving on to something new. The transition would work out just fine, I thought.

To some degree, it has. Right after the company was sold, I was able to make arrangements to do something that I’ve always wanted – go volunteer and live in the developing countries. So, within a matter of a few months, I jumped into that and decided that I’ll put off all of the planning about the future for when I come back.

Then, just what I hoped wouldn’t happen, actually happened. When I returned from my 7 month trip abroad, it was pretty quickly that I realized that I had no idea what to do next.

I didn’t want to jump into the industry that I’ve spent 6 years working in because I wanted to see and learn what else was out there. But to start anywhere else, you needed some industry specific knowledge and I still had this “sense of entitlement” that made it very difficult to be willing to start from scratch.

I jumped between ideas on starting a new business, buying an existing one, starting a job – just doing something that I could start building my new “identity” around. When I’d meet somebody that would ask me what I do for a living, I’d laugh it off and say “that my job is to look for the meaning of life”, but deep down, it was really frustrating me that I didn’t have an answer for this.

The bigger problem with all of this was that as days, weeks and months were rolling by, it felt like it was becoming even more difficult to get out of this sinkhole. After a while, the confidence that I’ve had when I built all of my previous businesses was starting to disappear. Instead, it was becoming replaced by a little voice that would come up every time I would explore a new idea: “Can you really do pull it off? Are you sure it’s not too much risk?”.

The fear to start something and fail at it was affecting all of my decisions. It felt that if nothing else, over the years, all of the companies I started were relatively successful and I can ruin this trend with a wrong choice. As a result, I ended up making no choices at all for some time.

It took some time to realize what was really happening and the consequences of what would happen if this were to continue. “Paralysis by analysis” – a situation where you begin to analyze each opportunity in a million ways and then ultimately find excuses not to do it – is the ultimate barrier to success.

The reality is that it’s often better to make a choice based on limited information and your intuition, then no choice at all. That’s not to say that you shouldn’t analyze and understand the opportunities you have at hand. However, you’ll often find that when you make a decision to pursue something, you start to see new opportunities that you haven’t anticipated and that things tend to work out better than you expected.

The biggest risk you have is not failing, but rather losing time and opportunities due to indecisiveness.

What This Blog is All About?

A little while ago, somebody asked me about the people that I most admire and why. As I made the list, I was surprised with the results.

Aside from the expected shortlist of family members and several close friends, the remainder of the list was shared a common characteristic – they were all bloggers.

There were a number of business bloggers – those that ran successful startups and companies. Then there were lifestyle bloggers – which were able to create a different and fulfilling lifestyle path for themselves. And a number that don’t fit in either of these categories.

As I was thinking more about why these people ended up on my “admiration” list, I realized that it came down to their ability to connect, teach and inspire their audiences. I don’t think that they are necessarily any more remarkable than any other people who accomplished challenging things in life, but it’s their willingness to share their experience, their ups and downs, and their lessons that makes them stand out.

One of my own long-term goals has been to create a positive impact on the lives of others, but for a long time, I’ve had a difficult time figuring out just how exactly I can do that. And while I’m still working on the answer – and will be addressing it in the future posts – I realized that the one thing I can do towards that is to share my own experiences on things that may be relevant to some.

This blog is called Quarter Life Musings, because it’s meant for people who feel like there is something more to be had from life and are not satisfied with following the old path. It’s meant for those who want to figure out how to make a positive impact in the world, find work that fulfills and inspires, and overall build a lifestyle that truly makes you truly happy.

It’s not for everybody. I think that plenty of people are happy where they are and many simply don’t want risk changing things. But if any of the following things resonate with you, I hope you’ll find at least some of this useful.

In general, the blog will focus on three themes:

Changing the World for the Better – We all want to make a difference. We all want to make the world a little better and contribute to the greater good. The problem is that we often don’t know how. Give money to charity? Volunteer? Even with all of that, it still often feels that it’s not enough.

Entrepreneurship and Work –  I find that more and more people (myself included) are looking for greater meaning and satisfaction from their work. It’s no longer enough to do mind-numbing paper pushing and get a paycheck every two weeks. We want the work to have meaning, to fulfill us, and to give us a purpose greater than ourselves.

Traveling With a Purpose – When you ask somebody what they’d like to do when they retire or when they have some leisure time, the answer inevitably comes down to – travel. Yet, on the other side of the coin, I also often hear how people go on a vacation and want to go home after 5 days or so. I truly believe that travel holds a key to a more fulfilling and rich life, but I think that just going places as a tourist often bores us.

Over the coming months, we’ll talk more about the problems and possible strategies and solutions to all of these things.

Am I an expert in any of these subjects? Hardly. I can only share with you the experiences that I’ve gone through and promise to be as transparent and open about it as I can.

I’m 24 years old. I’ve been self-employed for over 6 years; founded and sold several technology and publishing businesses. I co-wrote and published a book. I spent 7 months living and volunteering in Central Asia and India and traveled to about 20 countries so far (which I think is too damn little).

But it’s only the beginning.  I feel there is still so much more that needs to be done over the years, so I invite you to join me and push yourself just a little further and see what happens.