Letter No 108 - Multiskilling or moonlighting?

Dear friend,

I hope this letter finds you in a playful mood :-)

If not, then I hope this letter gets you a feeling bit playful. But even more importantly, since you have begun reading, I am sending you gratitude and energy. You will receive it. I am writing this letter with this संकल्प (sankalp) - a powerful, unshakeable, loving intent - that this letter will transmit some peaceful energy to you. Take a moment now to feel it.

Ok, lets begin.

This week, I want to dive into a topic that's becoming increasingly relevant in our ever-evolving world of work: multiskilling and moonlighting. Let's explore it together.


I am someone who is blessed to be able to wear multiple hats. Have you met anyone like this? It's like having a magical wardrobe filled with various personas. It's like being a graphic designer who's also a coder or being an teacher who doubles as a gourmet chef on weekends. I am able to a little bit of a lot of things.

I paint a little.
I play the guitar a little.
I sing a little (very little).
I run a little (have to restart).
I cook a little.
I coach a little.
I make pickles a little (once or twice a year).
I do public speaking a little.
I 3D print a little.
I make content for social media a little.
I lead a little.
I follow people who I love and admire... a lot :-)


I am multi-skilled.

Multiskilling is about embracing versatility. It's about acquiring and honing a diverse range of skills that not only makes you adaptable in today's job market but also opens doors you might never have imagined.

Consider for a moment that some of the world's most renowned polymaths—think Leonardo da Vinci or Benjamin Franklin or Rabindranath Tagore or Jagdish Chandra Bose—were celebrated for their ability to excel in multiple fields. While we may not all aspire to their level of genius, their lives remind us that being multifaceted has its rewards.


Of, before we move forward, here is a quick quiz.

Do you multiskill?

If yes, how do you feel about it?
A. Good. You love it.
B. Good. You like it but you feel confused where to focus.
C. Not good. You feel it distracts you.

If no, how do you feel about it?
A. Good. You are happy being focussed.
B. Good. You are not sure - sometimes you feel this way, and sometimes that way.
C. Not good. You'd rather be more multiskilled.

That was just a quick self-reflection. There's no right or wrong answer. But its good to know yourself and where you stand on this. If you answer a B and C it's a good idea to take some time for self-reflection and clarifying how you feel about this for yourself.

As for me, I believe it's good to get multiskilled in the kind of world we are heading into. There was a time when specialists were the need of the day. But I think today leaders and entrepreneurs needs to be multiskilled.

Here are 5 reasons why.

  1. Being multiskilled helps you be more creative and connect dots better
  2. It gives you the ability to have multiple perspectives to situations
  3. It makes it easier to have conversations with different types of people
  4. You are also to understand and empathise with people better
  5. You become more adaptable to changes in the world


Now, let's pause to differentiate between two closely related concepts: multiskilling and moonlighting. Multiskilling, in a professional context, often refers to the ability to handle multiple aspects within a single job or role. It's like a chef who not only cooks but also manages the kitchen staff and designs the menu.

On the other hand, moonlighting involves taking on additional work or part-time gigs outside of your primary job. It's akin to the accountant mentioned earlier deciding to offer tax consultancy services to individuals outside of office hours.

Both have their merits and challenges. Multiskilling can lead to increased efficiency within your current work and may even earn you a promotion. However, it can also lead to burnout if not managed wisely. Moonlighting, on the other hand, can provide financial security and an opportunity to explore your passions. But it requires careful prioritisation and clarity of your 'why' so that you don't end up just running on a treadmill but getting nowhere - neither in your day job, nor in your moonlighting profession.

In the next section I'm sharing some thoughts and perspectives on the trends related to both of these.


The Gig Economy and Side Hustles

The 21st century has ushered in the era of the gig economy and the rise of side hustles. Today, more than ever, people are turning to freelancing, consulting, and part-time work to diversify their income streams and gain greater control over their careers.

Consider this: the skills you possess may be in demand in various industries and markets. You might find that your expertise in digital marketing, for example, can be applied not only in your 9-to-5 job but also in helping local businesses boost their online presence as a side gig.

Passion Projects and Skill Development

Ah, passion projects! These are the endeavors that ignite your soul, whether it's starting a podcast, writing a book, or crafting artisanal soaps. Pursuing these side ventures not only brings joy but also offers an avenue for skill development.

Picture this: your fascination with astronomy prompts you to launch a stargazing club. Not only do you connect with fellow enthusiasts, but you also fine-tune your event coordination and public speaking skills.

Managing Time and Energy

There is an eternal struggle that goes on between managing time and energy when you're navigating multiple roles. It's like conducting a grand symphony with a hundred instruments, each requiring your attention.

Setting boundaries is essential. Just as the conductor ensures that each instrument plays its part in harmony, you must delineate your various roles.

And let's not forget the importance of self-care. Multiskilling or moonlighting can be exhilarating, but it can also be draining. Ensure that you're carving out moments for relaxation, reflection, and quality time with loved ones.

The Future of Work

What does the future hold for multiskilling and moonlighting? As we hurtle toward a new era of work, it's anyone's guess. The rise of remote work, automation, and artificial intelligence is reshaping industries and redefining what it means to be a skilled professional.

The next generation might find themselves navigating even more complex career landscapes. But remember, change brings opportunity. Being agile and open to acquiring new skills will be the compass guiding us through uncharted waters.

Seeking Fulfillment

Ultimately, the pursuit of multiskilling or moonlighting is about more than just financial gain. It's about finding fulfilment and purpose in a world that offers a multitude of paths to explore. Take time to understand yourself and your situation. It's important to get financial success AND fulfilment. This, according to me, is non-negotiatable.


As you ponder on this subject, I want to share two self-reflections with you.


The most important thing is to understand your own needs more clearly. Whether you choose multiskilling within your current work, or to moonlight with other opportunities, or some combination, being clear of your needs and the associated trade-offs will help prevent burnout, and yet keep growing in results and fulfilment.

Here are some of the needs we all have. I'm sharing them to get your thoughts rolling. They are not an exhaustive list. See them just as a thought kick-starter.

  1. The need to earn more
  2. The need to have diversity of people, place and work
  3. The need to build a personal identity
  4. The need to be a part of something bigger
  5. The need to have freedom to switch on or off
  6. The need to have stability and growth
  7. The need to work with a committed and smart team

Know your needs. Ideally, write them down. Write a few sentences of your thoughts for the needs that you feel are relevant for you. And then see what makes sense to you. Remember, neither multiskilling nor moonlighting may be the answer to your needs. Keep exploring. Talk to a few people you look. Tell them about your needs. Their thoughts may open open new perspectives.



Jobs or roles are not monolithic mountains. They are made up of many tiny rocks - many separate tasks. No job is made up of only one task.

Lawyers do not only make court appearances.
Surgeons do not only perform surgeries.
Journalists do not only write original articles.

It's important for you to
  1. Understand and list down the tasks your work is made up of
  2. Identify the skills required in each of them
  3. Then, think about which skills where you shine
  4. Also, think about which of the tasks might be easily automated by A.I.!
  5. Finally, think also about which skills you wish to deepen and develop yourself

These two combined reflections of Inner (self) and Outer (job) will help you understand your own work better, and come up with better directions and choices in your work and life.


Before we close this letter, I want to leave you with a thought: Your journey is your own. There's no one-size-fits-all answer to whether you should embrace multiskilling, moonlighting, or both. The key is to stay true to yourself, your passions, and your needs - and to stay PLAYFUL.

And now, it's your turn. Share your stories, your insights, and your questions. Let's embark on this multiskilling adventure together, and may it be filled with discovery, growth, and fulfilment.

Your stories, dear readers, are a source of inspiration. By sharing your experiences, you offer valuable lessons to fellow adventurers on this multiskilling journey. So, don't hesitate to contribute your wisdom, and let's build a collective treasure chest of knowledge.

In fratitude,