Risk Everything in Life 


Hey there!

Happy New Year! 😊

Did you miss me over the holidays because I missed writing to you terribly, but breaks are important, too :)?  

Anyway, I am back and would keep mailing you these bytes, as before.

I know you’ve entered 2021 with many goals to achieve. (Didn’t we all enter this year with the hope to cope up with the last one?)

But what are goals without plans and plans without risks we take to achieve those goals? 

You might have heard – Risk & reward go hand in hand. Higher the risk, the higher the gain.

Today, I want to talk about just that – the risks we take as a freelancer.

Let me share a story with you about the risks I took and the rewards I achieved.

I am sure you’d have your own version of this, and I would love to hear that. (Do email me the risks you took to start your freelancing journey.)

But before that, something on about 'risks'. 


Risk ≠ Gambling 

Have you ever played the roulette? (You must have seen it in flicks, definitely) 

The ball moves on the rotating wheel and no one knows which number it would land on.

When I first saw the roulette table in real-life (Don't ask me what I was doing in a casino :P), I smirked as everyone was gambling on in, excitedly, in the hope of winning a jackpot. 

Out of dozens on that table, I guess only a few managed to win some tokens that night.

Many people I met after that were just like the people I saw at the table – they want to be successful- as a freelancer, as a businessman, or as a marketer but they just resort to luck and gambling. 

No one talks of the risk and reward relationship, let alone the calculated risks.

Remember, your freelancing career isn’t a roulette table. And your winning chances aren't based on luck alone. Leads don’t land in your inbox out of luck. 

You only see results when you consciously take a calculated risk or work according to a plan. Right?

Risk isn't like gambling and you're never 'lucky'. You get rewarded for the risk you take in your career.

So, the next time anyone says that you were lucky as a freelancer, just smile, smirk, and get back to work - risk everything you have for reaching a new height.

Just yesterday, I was reading a chapter in The Psychology of Money (If you haven't read it, I highly suggest this one) that talked about the relationship between risk, luck and success. (Chapter 2). 

In the entire chapter, Morgan Housel tries to establish a relationship between both and their impact on success. But he just concludes that nothing is as good or bad as it seems - you can never actually account for luck in life.  

But I believe calculated risks take us far in our personal and professional journeys. 

Take calculated risk to attract rewards on your doors 

You already know my journey, so I won’t repeat it. But when I left my job in 2017, it was not a gamble but a calculated move. I prepared for months before planning my switch to freelancing.

Yet, I risked everything I had – a decent salary, a schedule, a company to associate my name with, for my dream reward – the freedom that comes with freelancing. And in the end, it helped me enormously –professionally, financially, and personally, even.

All I want to say is that don’t worry about the risks that come with that dream project you’ve been waiting to handle, or the dream client you wish to pitch. 

Create a plan and account for risks, right from the beginning.

And if you’re still thinking if freelancing would be worth it and if you are fit for it in the long run, I am telling you, you’re in a better position than I was 5 years back when I decided to go full time.

I wrote something about how I managed to take the leap of faith by balancing my job and freelancing before starting as a full-time freelance. You can read the blog if you want some tangible action points and motivation. 😊

My point with all this? Just one: 

Don’t be afraid to take risks as long as you’re not planning to lurk around a roulette table.

I’ve compiled a few general pointers for you to help minimize risks (and take calculated risks) as a freelancer at different stages of your journey. Hope this helps.

How to take calculated risks while freelancing? 


1. Before you start freelancing

    • Have an emergency fund (at least six months of your expenses in a separate account)
    • Talk to your parents, partner, or friends (clear out everything beforehand – your plan, your goal, the support you need, your schedule)
    • Don’t fall into the trap of ‘online trends’. Only chase something if you can handle it yourself.

2. While freelancing with your job on the side

    • Check your employment contract, first of all. (Many companies don’t allow side hustles)
    • Talk to your manager and clear out your stand beforehand (You don’t want to be caught red-handed while pitching a prospect online)
    • Never use your office time or device for completing your freelancing projects  
    • Don’t try to hide your freelance journey (You’d raise suspicion)
    • Never ever work with your company’s competitor as a freelancer
    • Plan your exit strategy with a fixed timeline (You can’t keep juggling both the responsibilities for life) 

3. As a full-time freelancer 

    • Never start without an advance (even if you know the client)
    • Always draft a formal contract with a new client (use an eSign software to seal the deal)
    • Use milestone-based payment schedule to avoid heavy losses (Think of Upwork-style contracts)
    • Provision for bad debts, annually (You’d protect yourself from shocks)
    • Trust your gut feeling (If a prospect appears shady, don’t risk your time)
    • Start thinking of diversifying your income (Don’t rely on client payments, all the time)
    • If you are planning to sub-contract work, vet the freelancer with a personal project first. (Don’t end up goofing a live client project with a sub-contractor)

I hope to hear your ‘risk and reward’ story soon. I am planning to share a few on my new blog in the future. So, feel free to share yours and I might end up featuring yours. 😊


Till the next time, keep freelancing! 


Your freelancing companion 




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