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From salaried to being self-employed : Notes from my first year of entrepreneurship

29th Dec, 2021

During the first year of my entrepreneurship journey, I frequently noted, in my personal diary, the differences I was experiencing being self-employed as compared to being a salaried guy. I had taken the plunge after being an employee for a decade. Being fresh off the salaried boat, I could clearly observe the stark differences in the two work profiles. Interestingly, I also observed that these differences weren’t as obvious to my entrepreneur friends without a salaried past.

I recently came across these notes while looking for something else. Once my sense of nostalgia settled down, I realized that these could be an interesting read.

I often wrote on different aspects of the same topic weeks or months apart. I have combined and condensed such notes for readability below.

Taming uncertainty

(Nov 2017, Feb 2018)

Jumping from a job to entrepreneurship - the most baffling change I’m experiencing is uncertainty. Not reading about it or philosophizing about it, but experiencing it first-hand.

As a tech employee, I worked on the goals my department assigned to me. These goals became my north star. I threw hard work and determination to achieve these goals and my salary, increments and promotions worked out just fine. I was operating in a controlled environment.

But, I am now seeing that, as an entrepreneur, any amount of hard work and positivity doesn’t guarantee me success. I strived towards perfection when working on the last couple of product features. But, with next to nil user adoption, I now see that it doesn’t mean a thing. I may set myself a target of writing 20 blog posts and over-achieve that by writing 25. But, that doesn’t guarantee visitors, subscriptions or revenue. The tools that worked well for me for years do not work the same way in this uncontrolled environment.

I think the way to operate in this environment is to find ways to increase my odds to succeed. Instead of writing 20 blog posts, write 5 and find out if they work. If they don’t, find out why. And then, write the next 5 with those insights. Or, just give up on writing blog posts if it doesn’t make sense. Try something else that appears to have greater odds to succeed. Work probabilistically rather than throwing brute hard work at anything.

Getting out of the building

(Jan 2018, Mar 2018)

My job allowed me to live in a predictable routine while interacting with a limited number of people (colleagues, friends & family). This was very comforting. But, it also made me averse to get outside the shell of my comfort. And, living this way for years meant I could hardly strike a conversation, collaborate, ask for a favor, find common synergy or build trust with people outside my circle. Trying to do so makes me feel anxious and vulnerable.

But, entrepreneurship requires that I constantly reach out. I need to engage with potential customers for sales, digital marketers for feedback, website owners for marketing opportunities, past connections for references and so on. When in business, connections matter.

That stated, every act of reaching out is anxiety ridden because of the fear of things not working out. Also, the fear of not hearing back at all is even more disturbing than the fear of hearing a “no”. Indifference hurts.

The only way out is to not take these failures personally. Keep the ego aside. In fact, learn from the insights these failures bring. And use them to eventually reduce the future chances of failure. So, when you reach out and things don’t work out, learn from it and move on!

Learning to live with self-doubt

(Feb 2018, Apr 2018)

Every year on the job, I had a defined set of goals given by my manager. These goals let me know the path I needed to walk to succeed. This kept things crystal clear & there was limited room for self-doubt.

With entrepreneurship, there’s no task list available. There’s no map to traverse and reach the treasure. I may meet my target of meeting 40 potential customers. But, what if none of them convert? This uncertainty brings in a lot of self-doubt. And, constant self-doubt drains out all the energy and often causes irrational negativity.

The only real way to learn to live with self-doubt is to be okay to fail. And to value, not just success, but also the insights gained from failures. If none of the potential customers convert, I need to understand why that happened. Was it the wrong user-segment? Or, was it pricing, pitch, positioning or something else. Gradually fixing the things that didn’t work is the only way to increase my odds in the future iterations.

It’s okay to not know something

(May 2018, Jun 2018)

Having worked on software performance for a decade, I’m decently knowledgeable about it. But, somehow this made me believe I was equally knowledgeable about many other (unrelated) things. As a result, I believed I knew the solution to many things far outside my area of competence.

I thought - “a certain bookstore could sell more books if they would have a better website”. Or, “a certain team could have lesser support tickets to handle if they’d hire more experienced developers”. Also, “our company would be less affected by the US economy fluctuations if they’d also sell in the APAC region”.

I now realize that these were all just opinions. But, entrepreneurship isn’t about opinions - it demands action. And, it is only when I act over things, I can see the innate complexity of the workings of the world. Everything is in a certain way because of a certain reason.

The bookstore is OK with a substandard website because all their current sales are offline. May be, they are better off optimizing their current sales channels rather than investing in the new channels. And, someone may not be able to hire more experienced developers because of budgetary or cultural constraints.

Stop feeling the need to be knowledgeable about everything. Be ok to respond to questions with “I don’t know”. If something doesn’t seem right, it’s mostly because I do not understand it fully yet. Spend time better understanding it rather than pointing out its flaws. And, the only flaws that matter are the ones you can solve.

Getting off the productivity treadmill

(Apr 2018)

It was a regulation at job to work hard to achieve my monthly, quarterly and yearly goals. As a result, at the end of the day, I measured my productivity in terms of how close I was to achieving the set goals. Somehow, subconsciously, I had gotten into a habit of deriving my satisfaction from this. Any time I’d not be working towards these goals would make me feel itchy and less productive.

But, entrepreneurship involves unknowns and demands a lot of trial-and-error. Simply throwing a lot of hard work at things can make me feel productive for a week or a month. But, it is not the most optimal way to traverse uncertainty.

Be okay to sit-back and contemplate about things. Act swiftly, but only after having taken a decision. But, until that happens, be okay to let the things stay at the back of the head for a few days. Leave empty days to look at the problems from a distance for a more rational decision-making. It’s okay to feel itchy about this in the short-term from the old habits.

Be the jack of all trades

(Jan 2018, Feb 2018)

My job allowed me to focus on solving specific problems. In-fact, my salary and all the other benefits were aligned to take care of my other worries to ensure I specialize working on specific things. As a result, I ended up being good at the kind of things my job demanded - finding & solving software performance issues. But, really sucked at most other things. In fact, I did not even know the kind of problems that existed outside the zone of my work specialization.

In contrast, self-gig demands that I know about marketing, sales, pricing, finance, employee retention, product management, UI / UX, code architecture, deployment, competition and many more things. Of course, I cannot be an expert at all of these, but I cannot ignore any of these. Especially now, as I’m beginning things, I may have to do most of these - often in the same day or week.

This can be intimidating, but the best approach is to learn on the job. No one knows everything. And, it is OK to be humble and accept not knowing even the basics of something. This acceptance also brings an opportunity to ask honest fundamental questions and learn.

Also, some of these areas (like UI / UX) may appear dull from the previous experiences. But, these past experiences were in the seclusion of a limited job role. The same areas can be stimulating when having an entrepreneur’s eye on the larger picture.


Thanks to Niharika Varshney for reviewing the draft of this post.

You can follow me on my twitter. I mostly tweet about my web development, site speed and entrepreneurship experiences.
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