Working solo

An introspection on the challenges & rewards of leaving a job and working solo.

Nowadays, it is in fashion to talk about “following your passion”, “finding your true self”, “being an entrepreneur”, or “chasing your dreams”. These clichés often urge you to leave the current organization you work for, and to work solo.

So, let me get it out of the way upfront: Working solo is very difficult. It can be especially so after working for several years in large companies, as I have learnt first-hand over the last two years.

This post is my attempt to share what I have learnt of what makes “work” work (you can interpret that in more ways than one!), lay out the challenges of working solo, and end with the promised rewards of working for yourself.

De-constructing work

To understand the challenges of working solo, we first need to understand work. I have tried to capture my understanding of what work — as we usually understand it — does for us. Do take time to pore over this picture:

What work does for us, made at http://goo.gl/izCeXn

To clarify a few points from the picture above:

1. Work can be about self-expression & freedom, or it can be about servitude and the following of someone else’s idea(l)s.
2. Work gives to us, at a conscious level, our identity & purpose, a structure to our lives, an order to our days, a community of people to be with, money to satisfy our needs and desires, and a sense of safety.
3. At the same time, and more powerfully, work operates on a sub-conscious level, and is tied to our emotional well-being: questions of Other/Me, Doubt/Clarity, Shame/Self-worth, Anarchy/Order, Loneliness/Community, Fear/Confidence are all at play.
4. Organizations keep us in their service by feeding these needs of ours. The relationship can be a healthy, symbiotic one or an unhealthy, parasitic one. Either way, it creates strong ties of dependence that become harder to wean away from as time goes by.
5. Working solo means having the strength and willingness to be open to uncertainty, to shame, to anarchy, to loneliness, to fear and ultimately, to questions about your identity.
6. The rewards of working solo are to conquer your fears and become stronger, gain a clearer understanding of yourself, develop a more balanced relationship to work, experience the joy of self-expression and attain a greater degree of independence in your life.

The challenges of working solo

Now, before writing about the challenges of working solo, I do want to lay out a couple of points:

1. The picture above is also interesting if viewed through the lens of “What do schools do for us?”. At a superficial level, there are differences. However, at a sub-concious level, schools work the same way.
2. The reason I raise this is: if you have been through years of schooling and college, and have then worked at an organization for several years, then working solo is going to be very hard. You are just very used to all the things that you get (“for free”) at an organization to be able to let go and work effectively on your own.

So, what are the challenges of working solo? There are many, and the challenges are layered: you need to think of it as a game in which you level up daily. Let us examine each of the points above — in the order in which I faced them — and see how we can meet the challenge:

1. Ordering your day: When you start working solo, anarchy takes over quickly. The joy of working on your own can quickly turn into the morass of TV, pizza, aimless chores and empty diversions. Solution: set up a fixed place and time to work. Keywords: Discipline
2. Handling loneliness: No more office gossip, no more competition and one-upmanship, no more team drinking, no more bitching about the boss. Dealing with this can be very hard. Solution: find a community you can be part of. Keywords: Sangha, or community
3. Ordering your life: For three months you want to start a company, the next three months you want to contribute to a social cause and then you want to learn guitar. Focus, deadlines, progress, guidance, feedback — all that you were spoon-fed with are now absent. And then, as time goes by, there is a sense of doom and gloom that creeps in… Solution: set goals, make a plan and stick to it. Keywords: Plan & Persevere.
4. Measuring success: If you’re lucky, you may make more money working solo than you did in a company. Even so, this may not be the case for several years. With no money and no bonuses — the measures of success that you have grown up with — your self-worth will take a pounding. Talk of “measuring your success through happiness” rings like an empty platitude when everything else is an emotional whirlwind. Solution: Find a friend, a family member or a mentor you can talk to often. Finally, the solution is to grow to a level of maturity where money is only one of the parameters of success. Keywords: Friends & Family.
5. Falling sick: The first time you fall sick when you’re working solo can be very hard. Along with anarchy, loneliness, doom & gloom and a depleted self-worth, you now also have fear. Thoughts of your mortality and the safety of your loved-ones will creep in. Solution: Have friends and family near-by. Keywords: Caring.
6. “Who am I?”: A simple question at a party, “So, what do you do?” — this can stump you. A question from your spouse, “Oh, you’re not working — can you drop the kids off at school?” — this can rankle. A friend says, “Let me pay for that dinner, you’re not working” — this can hurt. The word “entrepreneur”, a catch-all word nowadays, seems meaningless. Solution: Live in the present, and walk your own path. Keywords: Meditation

The words above explain it in a long-winded way, but to put it plainly and simply: learning how to handle depression is the biggest challenge of working alone.

Just as coming up too quick for air can cause “the bends”, similarly, letting go too quick of all the structure of working in an organization can cause depression.

The trick, I believe, lies in patience, humour, optimism and space for failure. Cultivate these, and you can beat the depression that surely will knock on your door.

The rewards of working solo

I have made a strong case in the above section for why one shouldn't quit to work for themselves. To re-iterate: working solo is hard.

You are misguided and will be disheartened if you are doing it because of the pop-philosophy of “following your passion” or “chasing your dream”.

You will be soon disillusioned if you are doing it because “I can do this better and faster than I did at my large company” or “My place of work is big, bloated and inefficient.” [Note: I used to work at Microsoft for 10 years before starting out on my own! ☺]

You will likely be heart-broken if you are leaving your job starry-eyed with visions of “Indian garage start-up bought by Facebook” or “Indian freelancer dating Emma Watson”!

So then, why work solo? The answer is that if you persist, persevere and work through the challenges, you will be rewarded richly.

1. You will find your natural rhythm: Though you will start with discipline, over time, you will find your natural rhythm of work: you will work when you’re ready for work, work hard and focused when you’re working, and stop when you’re tired. This will feel good.
2. You will create or find a connected community, and yet know how to be comfortable when alone: If you win your battles with loneliness, you will emerge with a community that you have created or are part of that has more meaning than your earlier community of the workplace. At the same time, you will know how to be comfortable when alone.
3. You will find few things that bring you joy, and you will make your time count: Once you go through the highs-and-lows of trying many things out, you will settle on a few things that are important to you and that you want to contribute towards deeply.
4. You will “get over” success and failure, have an improved self-worth and form deeper relationships: Once you are motivated by people, and not by success or failure, you will form deeper relationships with your friends and family, and will have a more balanced and healthy relationship with your work.
5. The conquest of fear: This is a big one, so let’s pick two: health and money. If you can be comfortable with ambiguity and uncertainty in these two, then this itself will be a big reward.
6. Self-expression and independence: If you’re successful in your journey of working solo, you will emerge with a powerful self-expression that isn't limited by titles and roles, and that naturally leads to a greater circle of influence.

So, there you have it: a natural rhythm of work, deep motivation and commitment, a connected community of people, greater self-worth, deeper relationships, the conquest of fear, and self-expression and independence.

Sounds scary, and yet exciting? Oh yes, it is.

[Context: I worked for 10+ years at Microsoft before taking the plunge to work on my own. The above essay captures the challenges I have faced so far, and my attempts at solving these challenges. Battling these challenges is daily work, and they’re not yet all beat. But I do believe in the rewards at the end of the process — and so, I am going to continue to walk the path. Please leave a note, share your thoughts or connect with me if you too have shared similar experiences!]