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The Black Dog: How to Handle Isolation and Depression as a Freelancer

Today we’ve got a stellar reader question…my thoughts follow.

### 

Nick, 

I am already enjoying reading Upwork Domination.

As regards your question: 

If you could snap your fingers and eliminate ONE business issue, what would it be?  

The one business issue I am struggling the most with is self-motivation, probably some aspect of that is ‘imposter syndrome’ as generally I am not withdrawn by nature.  

Maybe this is caused by negativity caused by too much doomscrolling…  

To be more precise, the one issue might actually be about generally finding enthusiasm through periods of depression…  

All a bit dark and heavy but this type of melancholia has been an issue even for celebrated individuals such as Winston Churchill who struggled with depression, describing it as ‘the black dog’.  

I notice I suffer a lot less when I have money in the bank. Right now, when I need to be on my A-game, as money is at a low point, I am suffering from it a lot. 

I probably need to make some lifestyle changes, do more exercise etc. 

Ok enough now. Thanks for the info. I look forward to going through it and ideally becoming another of your official positive reviews.  

All the best, 

### 

Man, I could write a whole book fixing all of these issues. For now, you’ll have to accept a very long and rambling blog post. 

S, I believe you’ve thoroughly self-diagnosed everything that’s wrong with you—and I’m willing to bet my entire imaginary collection of Black Dogecoin that every individual reading this email right now has experienced at least ONE of the issues you’re describing. 

I’m going to jump around and tackle these one by one. 

OK? Right then… 

Lifestyle Changes 

Specifically exercise—start here first. 

Active people are happier and more mentally resilient. 

You don’t necessarily have to get ripped or become ‘marathon-ready.’ 

But the vast majority of us are wasting away at a desk for the better part of a day—that is NOT how humans lived throughout most of history. 

Even walking for half an hour every day will do wonders for your brain wrinkles. 

Exercise makes you physically healthier, which directly affects your mental health—but there’s more to it than that. 

Those who exercise now view themselves as ‘someone who exercises,’ which creates a positive identity you want to maintain. 

Nice feedback loop. 

Next… 

Doomscrolling 

Have you watched The Matrix? 

Where 99.9% of humanity is plugged into a high-tech virtual reality coffin? 

Well, The Matrix is real. 

But it doesn’t look like a coffin—it looks like ‘infinite scroll.’ 

Reddit, Instagram, even LinkedIn… 

Every online platform is designed to sap your energy and convert it into currency for that platform’s owner. 

I don’t care if you’re watching college students snort mayonnaise on TikTok, or radicalizing yourself on Reddit political memes—it’s ALL designed to siphon your life away. 

You KNOW, deep down, that you’re wasting your time…and that makes you feel like crap. 

There’s no trick to disengage yourself. You just need to stop doing it, cold turkey. 

Imposter Syndrome 

I’ve written about imposter syndrome a lot in this newsletter, but I never get tired of talking about it. 

In the interest of saving time… 

Imposter Syndrome comes from a lack of experience. 

You overcome “I don’t know what I’m doing” by…doing. 

The problem I see with a lot of people is that they ARE experienced… 

But every time a slightly different version of the same problem pops up, people with Imposter Syndrome get too deep in their heads… 

And that slightly different problem becomes a brand new problem that you’ve never solved before. 

For example, say you’ve written 10 sales pages for different SaaS companies. 

You doubt your ability to deliver the 11th sales page because ‘this market is different.’ 

Or ‘this founder isn’t as marketing savvy so he won’t appreciate me selling too hard.’ 

And so on. 

These are all excuses. 

In reality, your range of expertise is much BROADER. 

If you’ve written a sales page for a SaaS company, you know how to write a sales page for a coaching program. 

Or emails for a health supplement. 

See where I’m going? 

You’re boxing yourself in for no reason, and let me tell you every successful person’s dirty secret: 

EVERYBODY is faking it. 

More money means more happiness BUT… 

Yes, money does bring happiness. 

How can it not? 

More money means freedom of pain, inconvenience, time…everything. 

BUT… 

While you’ve pointed out that you feel more enthusiasm for LIFE when you’re making more money, I must make this very clear: 

Money is INVERSELY correlated with the ambition to make MORE money! 

Meaning… 

The more money you make, the less pressured you feel to make more money. 

It is VERY difficult to maintain a steady state in life. 

In my experience, I’m either declining or rising—never truly ‘stuck.’ 

What we mistake for periods of stagnation are really periods of very slow, insidious decline…that we don’t realize until we’ve hit rock bottom. 

When you’re booked solid with good clients and making money hand over fist, you get comfortable. 

When you get comfortable.. 

You go into MAINTENANCE mode. 

Now you’re playing not to lose instead of playing to win. 

Playing to keep what you have, instead of winning more. 

You stop sending outreach to potential new clients. 

You stop working on your business. 

You start slacking off. 

Then slowly, like dominos, you lose one of your clients. 

You have surprise expenses. 

Things start to fall apart. 

And you’ve lost the killer instinct that got you here in the first place. 

You may have heard this saying: 

Good times make weak men. 

Weak men make hard times. 

Hard times make tough men. 

Tough men make good times. 

And so on. 

But every man and woman goes through this cycle on a personal level many times throughout their lives. 

Again…there’s no ‘hack’ to keep up your enthusiasm. 

You just have to force yourself to continue doing the things that got you there…even after you’ve already gotten there. 

Booked solid on Upwork? 

Occasionally send proposals and waitlist clients who you’d like to work with. 

You might even find a BETTER client than the ones you have now…instead of waiting until next month when you have NO clients, and panic starts to set in. 

And speaking of clients… 

One of the fastest and easiest ways to find more clients is…

Reading my emails.

“Thoroughly enjoy them” just like S did by clicking the link below: 

Fear itself, 

Nick 

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