7 Reasons Why You Shouldn’t Take Your Side Hustles Full-Time

Jul 27, 2021
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The grass isn’t as green as I thought it would be.

It’s been a month and a half since I took my side hustles full-time and it’s been a less than perfect start. Spending two weeks going insane whilst self-isolating in my room with covid didn’t help.

It’s more than that though and despite being an overanalytical gremlin, there were many things I got wrong. I’m anti-hustle porn but I managed to get tangled in it myself. I’m potentially more stressed today than I was before I quit.

Yet I still believe I made the right decision and I’m optimistic about the future. I don’t want to stop you from chasing your dream life but I want you to be better prepared for it than I was.


#1 Parkinson’s Law

Amardeep of two months ago was so naive. I believed I’d have so much free time once I quit my job. I could be a man of leisure.

Work crept up on me with a vengeance.

I found I couldn’t focus because I had the mindset of an abundance of time. I’d fail to get enough done during the day and end up working late into the night. The time I gained was swallowed up by decreases in productivity. It wasn’t supposed to be like this.

Parkinson’s law states “work will expand to fill the available time”. As a new entrepreneur, my ego thought I was above the law but I wasn’t. You might find the same. You won’t plan to waste time but it will happen by itself quietly as it did for me.

What to do about it:

I’m now tracking my hours religiously using Clockify. It allows me to track exactly how long I spend on different tasks so I can plan my days more effectively.

The act of being timed brings my competitive side. I want to avoid the embarrassment of a record revealing that I spent over an hour writing an Instagram caption. If you track yourself, you’ll probably be surprised at where your time actually goes.


#2 The crippling pressure

I’m sure writing used to be more fun.

Now I’m plagued by self-doubt and never think anything I write is good enough. I smash out the first draft then rewrite it until I’m not too disappointed in myself to press publish.

Today someone slid into my DMs and said how honored they were that I liked their post. It was kind of them but it triggered my imposter syndrome. I know I’m not terrible but I’m worried I can’t live up to people’s expectations. I can’t even live up to what I demand of myself.

If you love what you’re doing on the side, consider whether taking it full-time will steal some of your joy. Your perception may change when it’s what is paying your bills.

What to do about it:

People use their side hustles as an outlet from their frustrations with their day job. Yet when it becomes the main thing, they don’t replace the outlet with something new.

I launched my podcast last week which is like my side hustle. It gives me creative freedom without any pressure because it’s so new. This alternative productive use of my time has lessened the burden on my writing.


#3 The overburdening admin

It’s weird how most people don’t mention the hassle of sorting out their taxes when they sell the entrepreneur life.

Don’t underestimate how much of a headache getting everything in order can be. I have two separate companies and a dozen income streams. Most of my income is in dollars but most of my expenses are in pounds. Then different online platforms pay in different ways and need different forms.

You also need to work out the most effective way to pay yourself. How much of your take-home pay will be in salary and how much in dividends? What pension scheme will you use and how much will you pay in?

You want to be on the right side of the law but trying to understand it is a task easily procrastinated. Then the pile gets bigger and you have even more reason to put it off. It’s a vicious cycle.

What to do about it:

I’m lucky as my father is an accountant so can guide me through the system. If I didn’t have this connection I would pay a financial advisor. It’s worth paying to get it over and done with than fighting yourself for months.

It’s a good idea to do this before you quit to allow you to have the most realistic expectations. Everyone uses their revenue numbers when they post online, you might be shocked to see how little becomes money in their pocket.


#4 The volatility

I detest the toxic culture of entrepreneurs mocking people who are employed for valuing the safety of a consistent paycheck. Don’t listen to people who need to put you down to make themselves feel better.

Some people who take the side hustle full-time are fine with the volatility of their earnings. They find it exciting (or they do when it’s working in their favor). Then others like me aren’t risk-takers by nature and miss the stability they once had.

My earnings are all over the place and I have no idea what my income for this month will be.

Yet I’m in a privileged position with my savings and investments which made me comfortable enough to take my side hustles full-time. Please be careful of comparing the risk you take compared to others. Some dive into the unknown without a parachute but many have a secret backup.

What to do about it:

I’m giving up some of my freedom in exchange for a steady income. You don’t need to spend all your time on your own projects just because you are your own boss.

Evaluate whether a hybrid model of regular client income and your own risky projects works best for you. You can get the best of both worlds knowing you can pay your bills but also potentially shoot for the moon.


#5 The paradox of choice

Have you ever been frustrated when your boss has asked you to do something outside of your job description?

If you quit then there’s no more job description.

Everything is on you.

You’ve got to decide how you use your time and money. There’s no one else to fall back on or ask for approval.

This can be freeing but overwhelming too. I’ve got several hundred items on my to-do list now including my bloody taxes. Trying to pick what to prioritize and when feels like a choice I can never get right.

A day job forces you into a structure and to pick the highest priority tasks for your side hustles. You have the comfort blanket of the valid excuse of not having enough time. It’s bittersweet to lose that.

What to do about it:

I fall back to if-then plans when I get overloaded. I make the shiny things on my to-do list wait until I get the big one-off tasks done. For example, if I sort out my taxes then I’ll start writing a book.

If you mimic this for yourself, then you take away choice from yourself which makes it easier to plan the present.


#6 No more colleagues

I’m difficult to get a conversation with. I don’t shut up once you get me talking though. If you get half an hour of my time, you’ll find I’ll still be blabbering on an hour later.

I miss going to an office and having colleagues to chat with throughout the day. Solopreneurship can be lonely and Zoom calls aren’t the same as being in the same physical space as people for me.

In-person, you can easily tell when someone is busy and when it would be ok to chat. You can talk at the coffee machine for a couple of minutes then start walking back to your desk and the other person takes the hint.

If you like the energy of working with others, make sure you take this into account. I know many people love working alone but it isn’t for everyone.

What to do about it:

I’m inviting friends to come to my flat to co-work and it energizes me to have organic conversations throughout the day. This is great while companies are letting their employees be flexible with where they work from.

I know this might not last so I’m consciously making friends with other people who have control of their time in London. I may try coworking spaces too though fear I will be a distraction!


#7 Having to explain what you do

I’m jealous of those who have jobs everyone can understand easily. They get a nod of approval and recognition and the conversation moves on. I get a funny look when I tell people I’m a writer. Then I ramble as I try to explain all the different other things I do like editing, podcasting, YouTube, freelancing, coaching, and course creating.

It’s hard to explain I’m somewhat good at what I do without resorting to humble bragging in some way. I’m an online writer with millions of views. I’m an online writer with over 40k followers. I’m an online writer look at me. I make myself sick.

It comes from a place of insecurity. Two years ago if someone told me they were a blogger, I’d have judged them and thought they were having a minor life crisis.

If you take your side hustle full-time then be prepared to be expected to justify it to everyone who doesn’t understand what you’re doing.

What to do about it:

There are two ways to explain what you do. Either the big picture or the low-level details. My problem was neglecting my reason why and focusing on what my income streams were rather than my income river.

If you talk to people about your overarching mission, you’re likely to spark more interest than the mundane details. You don’t need to simplify things for other people. Treat your decision to take a different path as something that makes you more interesting not more isolated.

Amar's Letter

Real talk on driving impact as an imperfect human.