Being Honest Without Making Yourself Unhireable

As a freelancer who also writes online, I naturally have a lot of people in my network doing something similar. And every so often, I read something another freelancer has posted online and feel a very specific kind of pause.

I don't judge anyone or feel superior, because it's just not that kind of party with me. It's more like a quiet, internal, “Aw, damn, dude. Not sure I would have said that right out loud like that.”

If you're also someone who juggles both freelancing and blogging, you might know the moment.

It might involve someone being extremely honest about how broke they are right now, how impossible the market feels, how the system is rigged, or how everything is unbelievably shitty and getting worse by the nanosecond. I see it on Medium a lot and Substack, too. Sometimes it’s on LinkedIn (which is… a choice).

Sometimes it’s everywhere at once, like a touring one-person show called Late Capitalism: The Musical.

And look, I get it. I really, really do. I have all of these same worries and struggles (plus a few really weird ones that are probably relatively unique to me). I live in the same broken economy. I pay the same ridiculously dystopian grocery prices and have mini-heart attacks whenever I see hamburger costs $11 a pound that week.

I use my writing and blogs as pressure relievers from time to time. But I've also had to learn how to be honest without broadcasting distress for the well-being of my brand.

The Lie We're Sold About Authenticity

Somewhere along the way, especially online, “authenticity” got rebranded to mean total emotional exposure. Say everything. Share it all. Process every last scrap of your existential dread in public. And if it really hurts, publish it immediately, preferably before the coffee kicks in.

If you don’t, you’re fake. Or guarded. Or “not being real.” Or, my personal favorite, “not brave enough.”

I don’t buy that. At all.

Authenticity isn’t about saying everything you feel in the moment all the damn time. It's about telling the truth with intention and discernment. It’s knowing the difference between reflection and recklessly exposing open wounds to the elements.

In other words, it exists somewhere between “so, I’ve been thinking about this” and “I am currently very unwell and have Wi-Fi.”

That said, I have a lot of things I absolutely write about publicly in the name of real talk and being open with people — uncertainty, disillusionment, money anxiety, getting older, feeling completely out of step with the world. But I try very hard not to write about those things while actively spiraling into the void. I also don't frame myself as someone who's waiting for the internet — or maybe the right client — to come rescue me from my own life (although I wouldn't exactly say no if it happened).

Same facts. Completely different signal.

As Freelancers, We're Containers More Than We're Applicants

I get why people tend to miss this, because no one exactly pulls you aside and tells you this when you make the questionable decision to become a freelancer. There’s definitely no onboarding packet titled So You’re a Human Fire Extinguisher Now you can read for guidance.

But when you’re a freelancer, you’re not applying for jobs in the traditional sense. You’re offering to hold something for someone else — a new project, their administrative stress, their SEO mess, or maybe a deadline problem currently screaming at them from Slack.

In other words, most clients don’t hire freelancers because life is perfect and peachy-keen. They hire freelancers because something is on fire and they would like it... well... to stop being on fire.

So when someone stumbles across a body of work online that paints a picture of a frustrated, defeated person who seems to experience a fresh crisis every Tuesday — especially if they’re considering hiring you — they’re probably not thinking:

“Excellent. A desperate person. Let us feast.”

They’re thinking, subconsciously:

“Does this person feel steady enough to take this off my plate without adding new problems?”

Most prospective clients look at that and think, “I do not have the bandwidth for this energy.” And then they quietly close the tab.

Why I Try to Avoid Oversharing My Struggles

Don't get me wrong. I'm hardly floating above reality on a cloud of passive income and affirmations here. I am certainly not immune to fear or even complete panic-soaked anxiety. I am not over here “manifesting” my way out of grocery math, either.

I worry about money, and I worry about the future way more than I know is healthy. I worry about what happens if things dry up or decide to go ahead and break in exciting new ways. A lot.

But when I write about those things publicly, I do it after I’ve digested them a little and only from certain angles. I write about patterns, lessons, tradeoffs, and perspective shifts. I also try to turn whatever I'm talking about into something with a takeaway for readers in a similar position. It's better for the reader, and it's better for me, too.

Because there’s a big difference between saying, “This is hard, and here’s what I’m learning from it,” and saying, “I am actively drowning, please bear witness.” One builds confidence and helps me reframe panic-inducing life stuff as useful experience. The other asks the reader to put on a life vest themselves.

Clients, understandably, aren't going to be all that interested in the life vest option.

Platform Matters More Than People Want to Admit

Medium and Quora readers love a good confession, kind of like LiveJournal used to back in the day. LinkedIn pretends it's all business but actually wants inspirational theater attached to a glossy corporate headshot. Personal blogs (like this one) usually sit somewhere in the middle, depending on how you use them and how much chaos you decide to allow through the door.

What I personally wouldn't do is treat every platform like a personal diary with SEO. Because every writer can (and should) have:

• Private processing spaces
• Semi-private creative spaces
• Public professional spaces

Not every raw thought needs to become content as is, and not every feeling necessarily makes a good brand pillar. Not every bad week needs to become a think piece, either. That's what personal journals are for.

So, How Do You Handle This Without Becoming a Robot?

If you’re a freelancer who also blogs and you don’t want to either lie or self-sabotage, allow me to share a few guidelines that have kept me out of trouble over the years.

Write from a place of clarity, not collapse

If you’re mid-spiral or on the verge of tears but also feel the urge to write it out? That’s the time for a journal entry, a walk, or maybe an aggressively long shower. Publishing can wait.

Separate venting from meaning-making

Venting is completely valid. We all do it (especially me). But it doesn’t need an audience every single time. Public writing works best when it offers synthesis, not just steam release.

Assume clients are lurking quietly

Because they are, especially these days. They rarely comment or engage, as they're not looking to announce themselves. However, they absolutely read and form opinions in silence, like cats.

Match the platform to the exposure level

Your personal blog can safely accommodate a lot more complexity than LinkedIn, while your trusty Substack newsletter can offer more nuance than Medium. You do not have to be the same everywhere, and in many cases, you shouldn't be.

You don't owe anyone proof of suffering

You don't need to "earn" work by demonstrating how hard things are in front of God and everyone. Struggle is not a résumé line item, nor should it be. Clients honestly just care whether you can solve their problems and be relied upon to do so.

You Can Be Human and Hireable

I absolutely detest the notion that you somehow have to choose between being real and being a professional, because you don’t.

You can be thoughtful, honest, tired, perceptive, disillusioned, funny, and unequivocally open about being over certain kinds of nonsense while still presenting as someone who can be trusted with responsibility. That means carefully choosing what you signal, and when.

You're not running a reality show (unless you are), so you're not required to livestream your entire inner life in exchange for likes, claps, or clicks. There should always be some things you keep to yourself.

It's called having good judgment, and when you freelance, judgment is one of the most valuable skills you can have.