3 Kinds of Complexities That Every Entrepreneur Should Be Ready For And How to Deal with them


One of the things that is as predictable as the fact that Sun will rise tomorrow morning from the East and set in the West in the evening is the fact that once a business gains momentum, complexity will creep into the business, which will then slowly stifle the very growth that led to the complexity.

So, what can we do about it:

One of the things that entrepreneurs can do about complexity is to expect it and plan for it in advance. In a fast growing business, there could be three kinds of complexity:

  1. Process or systems
  2. Business Model
  3. Mental Model

Lets explore each one of these in some more detail.

Complexity in our Business Processes or Systems:

This is the kind of complexity that is a direct result of the growth of the business. The teams put together processes and systems haphazardly as and when the needs arise. We can see this in our business, when our employees start complaining about the company having become too bureaucratic. People try to side-step processes and exceptions slowly start to become much more common.

In a nut-shell, this is self inflicted complexity.

There are two ways to handle these complexities:

  • Anticipate these complexities and plan ahead of time. This requires the COO of the business understand the way the business is growing and anticipate areas which need standardised processes and systems in place. When putting in place these systems, processes and policies in place, care needs to be taken that these systems are not designed keeping in mind the current need but keeping in mind the need for the next level of growth that the business is eyeing. There needs to be a balance that needs to be maintained in addressing the current needs, while at the same time the needs that the business will have when it hits the next level of growth, which comes along with its own set of complexities.
  • Deal with them when and where they show up: This method requires that you empower your employees to deal with complexity as and when it arises with clear guidance about what is acceptable and what is not. This method requires a culture where it is ok for employees to make decisions about policies and processes, as long as they keep certain basic rules in mind and inform everyone else about the change in the process that they are creating. This method when used effectively can be fast and give your business a great competitive advantage or on the other hand if not done well, can cripple your business with ever more complexity and may even kill it.

Complexity in our Business Models:

This is the kind of complexity that is a direct result of changing market-place dynamics. This means that there is a new dynamic playing out in the market and while dealing with these dynamics, we create complexity in our business model. It could be complexity in any of the 9 elements of a business model as shared in the business model canvas. We could end up targeting multiple customer segment with different products offering different value propositions. It could be complexity in the way we manage our relationship with out customers. It could be complexity in the way we partner. It could be complexity in the way we utilise our resources. It could be complexity in the way we are pricing our products or in the GTM. It could be complexity in hiring and training the right kind of people that we want in our business.

In a nut-shell, this is a complexity that we create in response to the market dynamics that are playing out.

This kind of complexity is difficult to get out of. It needs tough decisions to be made. Clearly defined and articulated strategic choices need to be made. Product lines might have to be trimmed. Old partnerships let go of and new partnerships forged. Simplification of a business model level complexity is not a trivial thing but still can be managed, as long as we can decide where our future lies.

Complexity in our Mental Models:

The last and the most difficult type of complexity is when our mental models become complex. This is both a good thing and a bad thing, as with anything important.

This is a really bad thing if this is not a result of deliberate effort but has creeped up in our thinking. This is when we are unable to think clearly. We are unable to make trade-offs that need to be made. This is when paralysis by analysis takes route. We start doubting everything including our ability to steer the ship. The biggest challenge here is that it is extremely difficult to realise that we are in the clutches of this kind of complexity.

However, if this is a result of deliberate attempt on our part to cultivate our ability to engage in Janusian thinking, this is a good thing, As this allows us to not only make strategic trade-off’s, but allows us to hold opposing and contrarian views at the same time when making decisions. This gives us the ability to build in nuances in our decisions which are difficult to counter. This is when we are able to tackle multiple challenges with a single, simple and elegant solution.  As F. Scott Fitzgerald famously put it:

“The ability to hold two opposing ideas in mind at the same time and still retain the ability to function is the sign of a first-rate intelligence.”


Typically each one of these complexities will arrive in your business every time we grow our business by Five times. We need to be prepared and expect these complexities and be ready for them. We live in a world full of turmoil and complexity. It impacts everyone – us entrepreneurs, more than anyone else. Great entrepreneurs don’t run from chaos, they run towards it. As there is always a lot of opportunity amongst chaos.

How we manage each one of these complexities define how far we will grow as a business. I have in the past also shared a different model (Heart-beat Model of sustainable growth) of running a business which allows us to not only expect these complexities but plan and exploit them instead.

Importance of Silence and Reflection in the Life of an Entrepreneur


We are living in a world where there are just too many demands on our attention as entrepreneurs. There is the internal chatter about our people, products, processes, etc. Then there is the external chatter of marketing, networking, selling and to top it all off, there is social media and NEWS (fake or otherwise). Add to this there is a huge movement about increasing productivity. Every other blog (at times, this one included) tries to gives us hacks that can help us increase our productivity. So, in this environment, it is quite natural for us to try to use all our time and attention to maximise our productivity.

However, it is critical that we don’t get sucked into this seemingly logical thing to do.

Importance of Silence:

One of the most important things for us, as entrepreneurs, is our ability to make connections that others miss, see opportunities that others are blind to and be creative. Generating good ideas and connections requires us to look at things from different perspectives, which can happen when we give ourselves some quiet time, to think and reflect. It is this reflection that gives us the ability to connect seemingly unconnected stuff. It is reflection that enables us to bring our best creative self.

Author JK Rowling, biographer Walter Isaacson, and psychiatrist Carl Jung all have a practices for managing the information flow and cultivating periods of deep silence. Cal Newport talks about how he has stayed away from social media and does what he calls Deep Work (You can listen to my podcast with him here) that allows him to be super-productive at what he does.

Recent studies are showing that taking time for silence restores our nervous system, much like deep sleep. Silence is our pathway that allows us to get into contemplative states. It is during this state that we allow our minds to tap into our sub-conscious, creating the opportunity for connections of apparently random stuff, thereby allowing us to be creative.

Cultivating silence, as Hal Gregersen writes in a recent HBR article,  “increase[s] your chances of encountering novel ideas and information and discerning weak signals.” When we’re constantly fixated on what to say/write/tweet next, it’s tough to make room for truly different perspectives or radically new ideas.

If you are a typical entrepreneur, you will also find embracing silence to be extremely difficult and irritating.  What we need to understand is that cultivating silence isn’t just about getting away from social media or office chatter but it is ow we make time for reflection. When used well, it can also help us become better listener and increase out mindfulness.

We also need to understand the work pressures that we have to deal with and so it is critical that we are intentional in our need to set time for reflections. So, we need to put in place deliberate practices that create opportunities for us to incorporate silence  in our incredibly busy schedules.

Here are four practical ideas that can help us:

1. Two Minutes of silence before every meeting:

We can all do really well if we can have at least 2 mins (ideally 5 mins) of silence before any meeting that we attend. We can use this to meditate or even take some deep breaths. We could use this 2 minutes to reflect on what we are trying to achieve from this meeting. We can even think about what kind of mental state do we want to be during this meeting. Imagining how would someone we really admire run this meeting, puts us in the right frame of mind for the meeting. This also makes every meeting that we attend intentional. If we can’t come up with our objective for the meeting, we can start to re-look if that meeting needs to remain on our calendars. This also helps us defeat attention residue. It is now well-known that when we switch from one task to another, there is a short period of time when we are carrying our attention from the previous task into the current task. By taking the 2 mins silence between every meeting, we force ourselves to get rid of this attention residue thereby being fully available for the current meeting.

2. Movement:

A lot of creative people, when asked about their most creative moments talk about moments when they were in motion. For some it is when they are in a shower, for some it is when they are walking or running, For some it is when they are cooking or gardening. Each one of us needs to find out what it is that we could do that provides us the movement and also allows for self-reflection to happen inside of us. We need to schedule this on our calendar as a daily activity. This creates a habit that allows us to reflect on what is happening in our lives, which allows for creativity to emerge.

3. Nature as a companion:

We need not be an outdoor person to go into the lap of mother nature. Once a month nature retreat, where we are all alone, with no distractions, in nature’s lap, is an experience that one needs to have to know its impact. Being immersed in nature can be the easiest option to improving our creative thinking capabilities. Again, this needs to be scheduled and needs to be an activity that we do by ourself. What we could also do, is to take our leadership team into the woods with a clear instruction that each one is expected to contemplate and reflect upon the current reality, struggles and challenges that each one of them is facing. They are not allowed to talk to each other during this afternoon. We could finish the retreat with a social get-together, if it can be arranged in the woods.

4. Go on a media fast 

Try turning off all devices for a day every month. This can be pre-scheduled with information about this shared with everyone who needs to know. We can also set up an emergency protocol, in case someone really needs us. Once this is done, we need to turn off all devices for the day. This includes our phone, tablet devices, television sets and anything else that has a screen. Use this day to connect with everyone around us fully and try to enjoy listening to our ambient noise, irrespective of where we live. The place I live, I have birds chirping in the morning and the traffic noise throughout the day. This allows us the opportunity to disconnect from our work and focus on something else. It is during such disconnection that our sub-conscious continues to work on the different things that we are working on. It is during this time that connections are made and creative ideas emerge. We just need to make sure that we have some way for us to capture these ideas without compromising the media fast.


The world is getting louder.  We are getting busier. And the demand for creativity is higher than ever. We can use silence and the ability that it provides us to contemplate/reflect to come up with creative ideas and also help us improve our productivity significantly.

Timing And Entrepreneurs


One of the things that a lot of entrepreneurs who failed in their first attempt at starting and running their enterprise attribute their failure to is – Timing. They complain that their timing was wrong. They were much ahead of time. The users or customers were not mature enough to adopt their product or service.

Some wanna be entrepreneurs use timing as their crutch. They are waiting for the right time to launch thier business. This is not the right time, the economy is not doing very well, or is doing too well. The timing is not really great from a personal stand-point.

Most successful entrepreneurs attribute their success to luck and timing. They say there were there at the right time and at the right place, doing the right thing. It is this narrative that creates a false sense of importance about timing.

In this short film, titled Timing, the team at White Flag Productions talk about the myth of “The PERFECT TIMING”.

Lessons Learnt:

Some lessons in entrepreneurship that I learnt while watching this film are as below.

Perfect Timing = NOW:

There is no perfect timing. No, wait, there is perfect timing. We don’t find or discover perfect timing, we create it. We create the perfect situations and the perfect opportunities. How? By being present when they show up. Just like we need to be in the water if we want to find that great tide to surf on, we need to be in the game, in order to find the perfect timing. We will never catch that great tide if we are on the shore, waiting.  So, the right time to start something is now. The right time to do something is now. The right time to create art is now. The right time to create the change we want to see is now. The right time to be the change we want to see in the world is now.

Spiritual Suicide:

If there is a creator, artist or an entrepreneur within us and we don’t pursue that dream, it is like committing spiritual suicide. The missed opportunities and the lost time will always weigh on our soul and continue to give distress and pain all life long. As they say, the biggest regret that people who are about to die are about things that they wanted to do but didn’t. Let us learn from them and not allow the same regrets to enter our lives. Let’s not commit spiritual suicide.

Messenger of Misery:

As any creative, artist or entrepreneur will tell us, there comes a time in their journey when the messenger of misery will pay is a visit. Some call it resistance, some call it block and entrepreneurs call it a stall out. Just like there needs to be a moment in every Hero’s journey which tests the hero to the core, before transforming him/her into the hero that we can love, so it is in the life of every one of us. We should not only be prepared to deal with the messenger when she comes knocking on our doors but in a way expect and welcome her with arms spread out. This is a moment in our journey which will transform us from a mere mortal to a hero (hopefully!!).

Cometh the hour, cometh the teacher:

In Eastern philosophy, they say that the teacher appears when the student is ready. Not before, not after. It makes our lives easier as entrepreneurs if we believe in this. When we go for a stretch goal, something that we truly aspire for, something that seems to be so far away from our reach, we need to believe that when we are ready, our teacher will come who will help us uncover the hidden talents, resilience and the strength that is needed to achieve our goals. The teacher could come in any shape, form or figure. It could be in the form of a thought, a chance encounter, a random connection or even as a mentor. We just need to believe that the teacher will come.


In conclusion, I will only want to say this – “There is never a wrong time to do the right thing”.

Lets get started! Lets keep going!


What could Tiffany’s Do?


Last week the Wall St. Journal featured a story on Tiffany & Co’“midlife crisis.” The piece highlighted the jewellery brand’s struggle to regain its “cool” and improve recently tepid sales and profits. A few days later they announced the hiring of a new CEO.

Tiffany is hardly the only brand that is going through such a crisis. There is a lesson that all of us can learn from the experience of Tiffany and to a certain extent, even JC Penny. Steve Dennis on his blog talks about the customer trapeze. The customer trapeze is the idea of a brand hoping to reach a new, highly desirable set of customers while at the same time letting go of those with less favourable characteristics. Most often we see it at play when brands see that their most profitable demographic is ageing and at some point in the near future will start reducing their spends.

Knowing this, brands want to re-invent themselves to become more relevant to the new generation by becoming more hip or trendy.

The Challenge:

The challenge comes when they want to entice the new younger generation to engage with the brand, while at the same time do not want to alienate their existing client base, which is still generating most of their profits for them. This is a true catch-22 situation for brands. But is it?

Tiffnay has tried almost every trick that brands have in their sleeves – becoming more fashion forward, introduce less expensive items in their portfolio or attaching themselves to celebrities that appeal to the new demographic that they want to attract. What they are trying to do is to find the perfect moment when they can let go of their existing customers and take on the new ones. In Tiffany’s case, over the years they have introduced less expensive items and expanded their assortments in an attempt to widen their appeal to the new generation of shoppers. They have even taken on Lady Gaga and Elle Fanning as spokespeople and launched a new, more youthful ad campaign.

What could Tiffany’s Do?

I believe that this is a false dichotomy. I also believe that there is a simpler and a more easier way for brands to transition from one set of customers to another.

Option 1:

Create a new brand for the new customer segment. Let the old brand age with the ageing population cohort.

History reveals that very few established brands are able to successfully execute a dramatic re-configuration of their customer base–at least quickly. There is a significant risk in pursuing this strategy because, irrespective of what the brand does to do this switch, they will not be able to become attractive to both the ageing and the young cohort. In the process of trying this, they only alienate both the customer base, which ends up not so well with the brand and the brand dies a very slow and a painful death.

What is needed here is a mindset shift. What happens if companies create new brands for a new cohort of potential customers and continue to use the existing brand for their existing cohorts of customers. The existing brand can continue to remain relevant to their existing customers and even look at other things that the brand can do for the customers, keeping their brand values intact. In this case, in addition to creating beautiful jewellery, Tiffany’s could also look to create other items that an aging population needs – embellished walking sticks, reading glasses for the old. You get the flow.

What this approach does is allows a brand to live and stay relevant to a specific cohort of customers with their sensibilities. It is ok to allow a brand to age with their customers who grew old loving the brand.

Option 2:

The second answer is a bit more difficult.

Instead of trying to win the younger generation by themselves, allow their existing customers to do that for them.

What I mean here is the following: Instead of the brand trying to woo the next generation of customers and win them over, allow their existing customers (ageing population) do that for them. Then the question becomes what can the brand do for their existing customers so they can win their daughters and grand-daughters to their brand. This allows for two things to happen at the same time:

  • Strengthen their relationship with their existing cohort of ageing customers
  • Build a bridge for the new young customers to start engaging with the brand

This also means that the entire brand needs to go for a make-over and if done well, this can give the brand a new lease of life. The risk here is that if done badly, this could also very much fast track the death of the brand.


In conclusion, I will only say the following: how Tiffany’s and other brands in the similar situation handle it can have a profound impact on the brand – one way or other.



Start From Where You Are

One of the questions that a lot of wannabe entrepreneurs ask all the time is if there is a right age to start their entrepreneurial journey.

In this short video, Entrepreneur and business coach Marie Forleo shares a list of 10 women role models, who started their journey and late in their lives and went on to see a lot of success.

This only shows us that age is just a number. We need to start from where we are. Enjoy The video.

All you need is the problem that you are passionate to solve, some ingenuity, a good dose of creativity and a lot of hard work.

And as they say,

Let’s Go Make a Dent!