It was my absolute pleasure to speak to Belinda “Red” Weaver on freelance hustle culture. She invited me to speak to the students in her Confident Copywriting class. You can catch some of her work at For the Love of Copywriting community.

I have this funny habit that I often wrote out the notes for places I am appearing or speaking engagements I have been given- then I completely ignore them. I think it’s time that I repurpose that content and use it wisely.

Here’s probably barely what I said to Red as we navigated the hustle culture phenomenon. But at least it’s a good backgrounder into why we have hustle culture, some of the good things we can borrow from it. And some terribly stinky bits we can most definitely leave behind.

Belinda posed the questions; I gave the answers. Let’s get into some freelance hustle culture together, shall we?

Let’s start with hustle culture… how do we identify it?

a neon light on a wall reads hustle to demonstrate hustle culture. The room is dark except for the light.

Photo by Zachary Keimig via Unsplash

Hustle culture is a very slick marketing campaign of ideals we fought against because they were counterintuitive to our health. That is, the protestant work ethic of toil until you die and (hopefully) gain your reward dressed up as something glamorous.

I could be less sharp-tongued about this I suppose by breaking hustle culture down like this:

There are issues with overwork and hustle culture. It’s not compatible with physical or mental health. It doesn’t recognise privilege, and there’s a lot of blame in the messaging. If you don’t appear to be able to work yourself out of the hole, this is your fault. If you didn’t hustle enough, you didn’t succeed. Which, seriously, we need to address because there are barriers to self-employment, just as there are to standard working arrangements, that are created by privilege and inequity in society.

Beyond that, even working your butt off doesn’t ensure success. We have to stop personalising our relationship with work to the point where we allow mistakes and failures to loom larger than we should simply because we’ve tied the relationship to very winner versus loser style thinking.

We also have an uneven relationship with workaholism. It’s so normalised to be a workaholic, it’s seen as a badge of honour. And yet, workaholism can cost you your mental health, your relationships, your physical health and create even more toxic conditions like being an unreasonable and demanding manager. Or the tortured artist or the predatory culture that’s been exposed by movements such as Me Too. We allow people to suffer and create suffering for others under some mad genius mentality that at its core is embedded in that succeed at all costs hustle culture.   

Is hustle culture all bad or can we use it for good?

If you have anxiety, one of the best antidotes to it is accepting that you’re anxious. And then working through those feelings and moving toward things with deliberate action.

So, acting on your business isn’t so bad. Moving forward at a pace isn’t a problem. But acting without intention, purpose and aligned with your values is.

Workaholism is a lot of alcohol and the relationship we have with that. Having a glass of wine to wind down, not so much of a problem. Having a drink with friends, nothing unusual there. But when we can’t handle a bad day without wine or we can’t socialise without drinking, there’s a difference.

And this is the same with working culture.

Being applied and focused and wanting to work to achieve things is good for you. But when work becomes a substitute for your value in other areas. Or work becomes so important that essential aspects of your life like family, friends, fitness, being out from under obligation and that sort of thing play second fiddle, you have to start wondering what’s really going on here.

A lot of us have a strong ambition. We have goals. We want to succeed. When does this desire become unhealthy? 

For different people it can be that they’re willing to sacrifice their values in favour of a work win. Or when it becomes the only thing they can concentrate on or talk about. Or it becomes a way to sure up unhealthy relationships- like impressing parents or friends who see you as a 2d figure where school used to be what you were praised for, it’s now work.

Also, when it becomes a state of trying to convince others they’ve somehow failed because they’re not as interested in scaling every mountain, making all the money and so on. When we lose perspective about the importance of work in our lives, this is unhealthy.

How do we separate ambition and unhealthy hustle culture?

I believe not getting suckered by hustle culture is about you understanding why you got into self-employment in the first instance. It probably wasn’t because another freelancer was competing with you. You assumed the amount of risk that accompanies self-employment because you wanted to be at home with the kids or travel the world or to manage your mental health better or to prove yourself you could do something amazing you couldn’t find in a standard workplace environment.

So first and foremost, keep checking in with yourself as to why you started freelancing in the first place.

And then continually check-in by asking yourself a few questions-

1.      Are the trade-offs between work and my personal relationships well balanced?

2.      Am I excited by what I am doing and making intentional choices in line with my values and purpose or am I just in aimless motion?

3.      Who is this for?

Remember, no one wants “I was great at invoicing” or “I nailed the Johnson account” on their tombstone. Our clients won’t attend our funerals. And work friends, well, even in freelancing, there’s a fair amount of fair-weather friend stuff going on. Instead, look to be there for the people who want to be there for you.

When we enter hustle culture territory, what flags can we look out for?

1.      You have a fairly all or nothing approach to work.  

2.      You’ve forgotten how to look at the little steps that make the progress.

3.      You find it difficult to relate to people if not talking about work.

4.      You’re not sure of the purpose of it anymore but you’re always busy anyway.  

5.      There’s a lot of magical thinking “If I just fix this last thing”, “if I just work nights now”, “once I work hard this month I can…” that never seems to an end or is replaced by next month’s statement.  

6.      You’ve become the business equivalent of a door knocker trying to sell your ideals to everyone. Everyone has to be excited by work, everyone has to care about your work, and you’re very keen on telling everyone else how they should work.

7.      Life is generally out of balance.  

How do we temper/balance ambition and our mental health? 

Purpose, intent, wanting to achieve – heck, even stress- these are all healthy things. A healthy amount of stress or ambition or tension helps move us.

When it’s not healthy is when work has lost connection with these things. I work with a lot of freelancers who have moved away from the motivations and reasons they got into freelancing in the first instance. They’ve started modelling other people’s success and reading all the morning ritual posts. Before you know it, the reason they put their butt on the line no longer features. It’s all about competing and trying to outdo the other person on their own turf.

How you stay away from that is you stay close to your own motivations. The ones you had before you saw the other freelancer across the crowded hustle culture favoured conference room.

Some questions that help include:

·        Why did I assume all this risk in the first instance?

·        Have I met that goal and need to replace it? Or have I lost it and drifted away?

·        Am I happy with my personal life?

·        Do I understand why I am working the hours and making these choices?

·        Where’s the opportunity to grow?

·        How can I strengthen capacity?

·        What is my next challenge?

·        Have I made a difference today to my company, client, world?

·        What impact does my work make?

·        Would people notice if I wasn’t here?

·        What do I bring to the table?

·        Why am I the best person for the job?

·        How do I stay grounded and satisfied with the act of completion?

Having that balance and intentional working mindset helps you to be able to take advantage of the positive aspects of hustle culture and leave the stinky, unhealthy bits behind.

I’d love to talk about positivity. I like to think I have a positive mindset, but we’ve also talked about toxic positivity. Can you talk more about that?

I saw a fantastic meme the other day that summed up toxic positivity in relation to the hustle culture.

hustle culture with toxic positivity - Toxic positivity looks like- • Good vibes only • Just need to hustle harder • The bad only makes you stronger • No excuses Instead, let's try- • All feelings are allowed • It's OK to rest • That sounds really hard, I hear you • How can I support you? Not every bad circumstance needs a silver lining.

Toxic positivity looks like-

·        Good vibes only

·        Just need to hustle harder

·        The bad only makes you stronger

·        No excuses


Instead, let’s try-

·        All feelings are allowed

·        It’s OK to rest

·        That sounds really hard, I hear you

·        How can I support you?

Not every bad circumstance needs a silver lining.

How can we flag that and what’s a healthier approach?

Put your purpose and values at the centre of what you do. Have intrinsic goals to motivate you. And make self-care a thing. Get out from under the obligation of having to answer to clients, peers, kids, friends, your community- and make yourself a priority.

I am also a huge fan of active leisure. A film and a wine are fine. But if you’re finding that you can’t switch off from work, choose things that help you to make the mental switch.

Have an end of day ritual like changing your outfit, closing the door to the office, and taking the kids to the playground or the dog for a walk. Walk around the block. Slot in your exercise. Water the plants or pull out the craft supplies. Build a demarcation point between work and home life, even if it’s not clearly evident.

I also want to talk about mistakes. I think many of us rationally know that mistakes can be a positive influence on our strategies but how can we embrace failure in the moment?

We have to get comfortable with putting ourselves in situations where failure is likely a forgone conclusion. Some of the best moments in life I have had has been recognising I am not the smartest person in the room, opening my ears, closing my mouth, and taking it all in.

Girls as young as eight stop trying new things because if they cannot reach 100% competency, they don’t want to face the failure. Yet boys tend to crash on through and be far more comfortable with not being in poll position. We need to stop telling ourselves that if we don’t get it first time, we should stay away from it. Or that first prize is the only prize.

This is the root of the hustle culture- this idea that by any means possible, we should win. And that if we don’t win, it’s not worth our time. Well, we can’t win at everything all the time. But that doesn’t make other moments and achievements any less valuable.

Challenging failure is about perspective. So, “what can I learn from this situation?” is a great question that very few people actually ask themselves. Learning from it means you don’t lean into blame or try to paper over it. Run an autopsy. Look at the role you played. Look at the things you ignored. And figure it out honestly.

Also, put the mistake into perspective. That all or nothing thinking again is a problem here.

A mistake rarely influences everything. It’s rarely permanent. And despite what we get told, life is a heck of a lot less personally directed than we think. People generally don’t do things to us out of malevolence. They do it mainly out of being oblivious.

The same can be said of mistakes. They don’t happen to us because we’re a bad person or we’re a failure. They’re part of life. So, adopting a proper perspective and a growth mindset helps stop them looming so large they eat us from the inside.

What are some practises to keep us in a healthy zone when it comes to our mental health?

A life in balance and where respecting yourself enough means you will listen to yourself with an open heart and compassionate viewpoint.

Moderation may not sound cool, but enough sleep, enough exercise, time with work and time with friends, having breaks during the day, learning to be still just as much as focusing on productivity- it all matters.

I think too staying away from stinky thinking about yourself and others helps. Australians are probably a little too cynical and a little too afraid of failure. If I do something new for my business, I will invite an American or an English friend to be the first to hear the news these days because Australians have an unfortunate habit of saying “yeah good, but you missed a spot or why did you choose that photo?” – we’ve been kind of groomed to be unassuming and not to showboat to the point where we try and dampen people down a little. Which is a shame because I see it eroding confidence, that it stymies innovation, and creating this warped culture that perpetuates an inner dialogue that’s really tough to break away from.

Do you have any resources to recommend?

James Clear’s Atomic Habits is a good book for addressing thinking patterns and swapping out bad habits for good ones.   

Art will save your life by Beth Pickens – written by a counsellor who is queer and works with the queer artistic community after Trump got in, Beth’s book takes that feeling of grief and pain many excluded Americans felt and gives a roadmap to creating with intention. It also gives creatives, who often struggle of staying away from hustle culture too much to be able to earn a living, a practical way to break that cycle of similarly negative thinking about money.  

Do the work by Stephen Pressfield – actively counsels against making your brand your name to give perspective and also implores you to get the work done without making it all about you. All helpful messages I think if you find the glare of a spotlight on you as a person and a business a bit much.  

Also, use what you have available to you. Time is a resource to protect your mental health. And we’re far more creative when we give ourselves time to play. Problem solve, do stuff that doesn’t have to be seen on the internet or social media. Create for yourself. Have a project in the dark.

Want to know more about me?

I talk about content, culture, community and coaching here

Australian freelance advocacy and stress reduction can be found here

And if you want to study with me via courses such as “how to keep working when you’re dying on the inside”, “marketing for introverts” or “the accidental community manager” as well as other classes in business development, marketing, persona creation, pitching and more, you can get me live and loving up your inbox and screen via the Freelance Jungle Patreon.

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