3 Minute Monday – Self-Employment, Stress & Clues

Hi friend,

10 reasons why working for yourself absolutely sucks.

Pretty much everyone on the internet is telling you to leave your job and go work for yourself.

If you’re not already side-hustling your way to a million, you should flip your soyboy boss off as you hand in your resignation to finally carve out your own destiny.

But there are some huge dark sides to running your own business that the Hustle & Grind world will never advertise.

So allow me to enlighten you.

You are only ever accountable to yourself.

Not having to answer to a boss sounds fantastic.

No more pointless Tuesday morning meetings and no one whinging if you return late from lunch.

But that accountability provided structure.

Now, not only are you the guy doing the work, you’re the guy telling the guy to do the work.

So, no one is going to tell you off if you don’t do it.

The only person who pays that price is you.

After 18 years of running businesses I can tell you that being both the organ grinder and the monkey is exhausting and flipflopping from neuroticism to apathy is not a good situation.

Never knowing when you’re finished.

Many people start their own business to take control of their time.

But being in charge of your own workload means that there’s always something else to complete.

Instead of having a prescribed list of tasks to move through before 5pm, now you have a never ending conveyor belt of things to do.

Over time, your life can become invaded by a permanent sense that there’s unfinished work.

This Ambient To Do List Anxiety may well help you to stay competitive, but that doesn’t mean it will actually increase your quality of life.

Over time your typical finish goes from 5 to 6 to 7pm, and it’s very hard to turn around once you’ve started down that road.

This can turn into a vicious cycle of mounting workloads and increasing guilt leading to more work and more guilt and so on.

The price that you pay in missed events, time with friends and family and just opportunities to experience life is real.

Yes you ARE your own boss at work now, but your work has become the real boss of your life.

Attaching your sense of self worth to the success of the business.

I spent most of my 20’s feeling great when my businesses were doing well, and terrible when they were doing badly, even though most of their performance was out of my control.

This is a recipe for disaster.

You can do all the right things, release the perfect product, nail the marketing, capture the emails.

But ultimately the market doesn’t care about you, and will respond in the way it responds.

And especially if you’re a young entrepreneur, this is a real risk.

You’re basically outsourcing your sense of self worth to a fickle, fast moving economy.

Previously there was a buffer between your work and its outcomes, but now it feels like a direct relationship.

If you are what you do, then your value is how well you do it.

Very quickly this can turn from emotional investment into identity attachment.

Permanently having to create your own motivation

In a normal job, you externalise motivation to your colleagues and your boss and the company rules, but this support system is no longer there.

Even if you’re starting a business with colleagues and employees, the buck stops with you now.

If you don’t do it, it won’t get done.

And with no one but yourself to motivate you, this can become absolutely exhausting.

Now, not only do you need motivation to do the work but you need motivation to decide what to do and then tell yourself to do the work and then tell other people to do the work too.

This drains your willpower reserves for other things, not only in your business, but outside of it too.

Your motivation to train hard or stick to a diet or build a new habit will suffer because of how much effort you need to expend to keep your business going.

Holidays and downtime barely existing.

I spent 204 Saturdays in a row setting up the same clubnight and never took a holiday which lasted longer than 4 days until I was 26 because I was so terrified of leaving my business for too long.

I only went on one reality TV show because they promised that they could get me back to our event ready for the doors to open on a Saturday night.

Your competitive advantage comes from noticing things that your competitors don’t and being more detailed and creative and consistent.

This is the superpower of the small, agile, lean startup.

But it’s really hard to switch off.

Even if you manage to shoehorn in some time away, that doesn’t mean that your mind is also going to take a vacation from thinking about work.

Never being certain if what you’re working on next is the right thing.

When you’re the person who both makes the rules and follows the rules, you can get caught up spending time a lot of time questioning instead of executing.

There are no Standard Operating Procedures for you to follow.

Usually if you had a question about what to do next, you’d just ask your boss, this outsources the decision making and the culpability for getting it wrong to them.

Now, you don’t have that free pass.

Even after a while when you’ve created a typical working routine, the fact that you made the routine will always leave you with this distracting sense that maybe you should be doing something else.

No assurances about income.

Another reason people start their own business is because they want to be in control of making their own money.

No longer are your efforts and outcomes detached from each other.

Now, you take on the risk and receive the reward, but there are no assurances here.

The market doesn’t give a shit about you.

It doesn’t care how hard you’ve worked, you can do everything absolutely right and watch your revenue get chopped in half next month.

Some months you’ll double your income, some months you’ll make nothing.

You need to ask yourself whether you can handle this?

Really think about it.

In a normal job, you’ll receive your pay cheque no matter how the company is performing.

Some people are built for this monetary orderliness, they like stable, linear progression which they can predict and it makes them feel safe.

If you strike out on your own, you become your own pension, backup plan, holiday allowance, sick leave and pay rise all rolled into one.

Watching your financial security get ragged around at the mercy of market forces is not fun.

It becomes much harder to get a mortgage.

Buying a house or building a property portfolio is on many people’s list of financial goals.

If you’re in typical employment and have around a 25% deposit to put down, you can usually find a bank to lend you around 5 times your annual salary to buy a house.

If you’re self employed however, the bank will scrutinise your accounts much more closely. In the UK you’ll need to provide 3 years of SA302’s which are the Self-Assessments of annual income, plus they may dig even deeper into the sources of that to look at wages, dividends and any other forms of income that you’ve received.

I don’t know how it works in America but I can’t imagine it’s any prettier.

This means you essentially cannot get a mortgage if you’ve been self-employed for less than 3 years.

That might not sound like long, but if you’re holding up your ability to enter the market or move into a dream home, it will feel like an eternity.


Even if you have a huge, amazing team and a shithot assistant, you will have to deal with more paperwork.

Realistically, you’ll probably have to do most if not all of it yourself.

Articles of incorporation, bank accounts, trademarks, leases, business rates and then constant ongoing checks of these is beyond tedious.

Yes it’s cool to have a bank account with your company name on it, but no one talks about the headaches of submitting your annual expenses every year or dealing with enquiries from His Majesty’s Revenue & Customs.

If you’re administratively-minded you may be fine to deal with this, but if you’re already cutting it tight to meet a deadline, finding out at 3pm on a Friday that you’ve got an intellectual property dispute to deal with is an ugly situation.

Always feeling like your work could have been better.

You probably want to start your business because you’re passionate and talented at something.

But if there is one way to turn a love into a labour, it’s to monetise it.

You don’t know what time you’re supposed to finish, or specifically how you’re supposed to do the job, and you daren’t take any time off from doing it.

But even if you get past all that, you are now the final Quality Control check for your own work, and everyone else’s.

The amount of time you will spend double and triple checking work cannot be understated.

You will wake up in the middle of the night sweating because you’ve realised a slide is missing from tomorrow’s presentation or you’ll need to hotspot off a tour guide’s phone to update a link on the website.

This IS the entry price you pay for being at the top of the tree.

The buck will always stop with you.


The question you need to ask is, why are you thinking of working for yourself?

Presumably you want to be happy and satisfied with your job.

But all of the gains you make in increased freedom and money and input, each come with an associated cost.

You will use up willpower and spare time and sanity to make this happen.

You need to work out if that’s truly a price you’re willing to pay.


I do a podcast which has had 500 million+ downloads. You should subscribe on Apple Podcasts or Spotify.

This week’s upcoming episodes:

Mark Normand – one of my favourite humans on secret Hollywood rituals, new swear words, staying positive in a cynical world and more.

Coleman Hughes – a great breakdown of how race politics has overtaken modern life, whether it actually helps minorities, the idiocy of anti-racism and what a better vision looks like.

Cal Newport – the creator of Deep Work breaks down his new book Slow Productivity. Very good antidote to frantic hustle culture, practical, philosophically insightful. Don’t miss this.


Having a clue is overrated.

There’s this funny myth that people actually know what they’re doing.

I’ve spent time around some of the richest, smartest, highest status people on the planet.

And let me tell you, it’s idiots all the way up.

Normalise saying “I don’t have a clue, I’m going to work out how to do it anyway.”

Why you are stressed.

“Stress doesn’t come from hard work. Stress primarily comes from not taking action over something that you can have some control over.” — Jeff Bezos, 20 years ago

Beware of the story you tell yourself.

The story we tell ourselves is the most powerful one in the world.

Eventually, we start believing it, even when it’s not true.

While a positive story by itself won’t guarantee a good outcome, a negative one will certainly prevent it from happening.

“If an idiot were to tell you the same story every day for a year, you would end by believing it.” — Horace Mann, h/t Shane Parrish


Ring your mum.

We all need this reminder more.

Big love,
Chris x

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