The freelancer I don't want to be, and what hiring others taught me

You won’t believe how hard it is to find a good freelancer.

I’ve always been on the freelancer side – that’s my comfort zone, my business, the career I’ve built over years. But when I started looking for creatives for Deeply projects, illustrators and designers who were supposed to help with client work, I found myself on the other side for the first time. In the client role.

And you know what? I was shocked.

Not because everyone was bad or unprofessional, but because so many talented freelancers with great portfolios don’t know basic things about working with clients. How many people fail at elementary things in the process – communication, timelines, setting expectations – things that have nothing to do with creative skills but everything to do with running a business.

It was a wake-up call.

And now I understand my clients much better than I ever did before.

What actually happened

Here are a few real situations that happened to me over the past couple of years searching for collaborators:

Story #1: The disappearing act

A freelancer took on the work, we discussed everything, agreed on terms and timeline, and work started. And then, right in the middle of the project, they disappeared. Just stopped responding to messages. A week later they finally wrote back saying they couldn’t continue and returned the money.

The money came back, yes. But the deadline was blown, my client was waiting, and I had to urgently find a replacement and redo everything from scratch under impossible time pressure.

Story #2: “Everything’s under control”

The deadline is approaching, so I check in – how’s it going? “Everything’s under control, I’ll make it.” Deadline passes. “Sorry, just need a couple more days.” Another week goes by. “Almost done, just a bit more to finish.”

This repeated 5 times. FIVE separate times.

Not once did they say “I’m not managing this” or “I need help” or “let’s reschedule and be realistic about timing.” They kept giving hope that didn’t materialize, over and over again, leaving me unable to plan or find alternatives.

Story #3: Expectations vs reality

The portfolio looked incredible – cool work, strong style, everything seemed on point and exactly what I needed for the project. I was excited to work with them. Got the result and the quality was much lower than what was shown in their portfolio. Not that it was bad work, but it definitely wasn’t the level I was counting on based on what they’d presented.

Story #4: Communication like with a buddy

They respond once every three days, messages are short and incomplete, questions get ignored or answered only partially. I don’t expect formality or corporate language, but basic professionalism is the minimum when you’re working with a client, not hanging out with a friend.

The pattern I noticed

What connects all these stories?

→ Lack of basic communication. Not saying in time that something’s wrong, not warning about problems before they become disasters, not keeping the client in the loop about process and progress, not clarifying what’s unclear instead of making assumptions.

→ Not understanding how to actually work with a client. Many creatives do great work and have real talent, but they don’t know how to work in a professional context. How to communicate clearly and consistently, how to set realistic expectations, and how to share their process so clients aren’t left in the dark.

And here’s what really surprised me – almost nobody shared their work process upfront, even though this is incredibly important for successful collaboration. The creative field is one big umbrella, but everyone works completely differently with their own stages, checkpoints, and approaches.

For the client – for me in this case – it’s crucial to know what exactly I’ll get and when, what the stages will be, what your process looks like, and when to expect basically anything from a freelancer. This all needs to be discussed at the start, not assumed that “it’s obvious” or that everyone works the same way.

What this taught me about my own freelancing

I didn’t make these mistakes before, and I don’t make them now. But this experience of being on the other side made me significantly more thorough and intentional in how I communicate with my own clients.

Now I always share my process upfront – I explain the stages, when what will happen, how we’ll work together and what they can expect at each point. I warn about problems immediately if something’s going wrong, so the client finds out right away and not the day before the deadline when it’s too late to fix anything. I keep clients in the loop even when everything’s going perfectly according to plan with short updates between stages, so they’re never left guessing or worrying about progress.

And I respond professionally – warmly and personally, yes, but not like I’m chatting with a friend. Full answers to questions with all the context they need, not fragments or one-word responses that leave things unclear.

And you know what? My clients constantly mention in their reviews the ease and clarity of working with me, how simple and stress-free the process feels.

This isn’t a coincidence or luck – it’s because I’m intentional about these things.

What freelancers need to understand

If you’re collaborating with other creatives, agencies, or studios, you’re working with a client even if the relationship feels casual or they’re “your people” in the industry.

Here are the basic things that should be default, not optional:

1. Communication is part of the work
It’s not just about doing the creative work well – it’s also about keeping people in the loop, responding on time, and clarifying what’s unclear instead of guessing.

2. Share your process
Don’t keep everything in your head assuming others will just figure it out. Explain how you work, what stages there will be, when the client will see what, and how feedback will happen.

3. If something’s wrong – say it immediately
Don’t drag it out until the last possible moment hoping it will somehow fix itself. Don’t give false hope because you’re afraid of disappointing someone. It’s always better to warn in advance and adjust the plan than to let someone down at the deadline when there’s no time to recover.

4. Portfolio = promise
If you show work of a certain level in your portfolio, the client expects exactly that level for their project. If you can’t consistently deliver that quality or it was a one-off lucky piece, don’t show it as representative of what you do.

5. Professionalism ≠ formality
You can absolutely be warm, friendly, and human while still being professional in how you work. Answer fully and thoughtfully, respond on time, communicate to the point.

Being on the other side of the table – hiring instead of being hired – is sobering in the best way.

I understand on a visceral level why clients value reliability and clear communication more than pure creative talent, and why good process can be more important than a stunning portfolio. Both matter, obviously, but one without the other creates problems.

And I also know exactly what makes me a good freelancer to work with – not just the quality of my creative work, but how I work, how I communicate, and how I make the entire process feel easy and trustworthy for clients.

If you’re collaborating with someone, working on a team, or taking projects from agencies or studios, remember this:

basic professionalism isn’t optional or something you add if you have extra time. It’s the minimum, the foundation that everything else is built on.

Happy to help you work through your process and communication in a coaching call so you can avoid these mistakes and build stronger client relationships.

Thank you for reading,