The challenges of full-time freelancing that no one warned me about

Marijana Kay
6 min readAug 28, 2017

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Going from a full-time role into self-employment didn’t come naturally to me. Now, I’m happier than I’ve ever been, but this didn’t come without challenges — I’m sharing them below with you. Let me know if you feel the same!

My routine literally doesn’t exist unless carve it out

Most of the times, a standard full time job comes with a routine, regardless of the hours, shifts and the nature of the job.

It’s simple: you know when you need to show up. After a certain amount of hours, you go home. Easy.

When you’re self-employed, however, and you’re working from home and you literally don’t have anyone else to liaise with… Things become a challenge.

I’m usually a productive person, I LOVE writing, and I just thought “Well, I’ll just start writing and write for as long as I need to, and I’ll be fine, right?”

Might work for some people — it doesn’t work for me. In order to be productive, I need to create certain conditions. I am ridiculously easily distracted and unless I set a schedule for myself, there’s very little chance that I’ll just wing it by working from my bed.

I’m most productive in the morning, and I’m in the process of creating a daily routine that will make me do the most attention-requiring work then. I also need to be sitting at my desk and have a tidy environment. I’m testing out calendar blocking, the Focus@Will app that allegedly combines neuroscience with music, and the amounts of tea necessary to get me working. I’ll let you know how it goes!

A quick side note: I’m not saying that the usual 9–5 that comes with office jobs is necessarily a productivity booster… It’s often quite the opposite, at least from my experience. It does force you to show up at a certain time, though, which is absent when you only need to show up at your home office in nothing but your pajamas.

Time becomes VERY relative

This is both a challenge and a blessing.

When I was in my full time job, I often felt that a week could go by without me realizing where it really went or what I’ve accomplished during this time. Days felt incredibly short and weekends seemed rare. (Weird, right? Weekends happen every week, but it surely didn’t always feel that way.)

So many things are different now. First of all, I have about 90 extra minutes in my day because I’m not commuting anymore (that’s over 7 hours a week, by the way — a whole extra day!). Days feel incredibly longer. On Wednesdays, I sometimes feel like the whole week’s already gone because I’ve done SO much in these 2–3 days, but I’m not exhausted as a result!

Another thing is that time feels like it goes so much faster when I’m working. This is a challenge on its own because I love what I do, but I think that’s the exact reason that makes the time fly. You know that feeling when you’re in a job that exhausts you, and 8 hours feel like eternity?

Me too. Never again.

Being my own boss means I’m running a business

I’d love to tell you it’s all butterflies and rainbows and I’m now living in a land of endless writing where no one at all ever affects me.

Yes, they do: my clients, prospects, the tax office, the bank, and a long list of others.

Admin work and emails can easily take up hours upon hours each week. There’s almost always a way to improve processes, but they can’t be completely avoided.

And then there’s also the stuff that you never EVER have to think about when you’re an employee… Branding, marketing, social media, networking. You can easily survive years in a company without ever thinking of these. Being self-employed? Not so much.

Building a network and a community takes time and effort. As does running a business, no matter how small.

I’m still obsessed with it and wouldn’t trade it for anything else, though.

People may not necessarily understand

Most often, they don’t really mean anything bad and they are not trying to be mean.

But people do think and assume all sorts of things when you say things like “I’m self-employed now”, “I’m a freelance writer”, or simply something like “I quit my job so I can finally do what I want”.

Some of the worst reactions I’ve received…

“Isn’t that really low-paid work? How is that making you happy?”

“It’s good that your husband is working, he can provide for both of you now”

“What do you mean, self-employed and pursuing your passion? When are you going to look for a job?”

When you quit your job for the challenges of working for yourself, it’s uncomfortable, uncertain and hard as hell, particularly when you’re just starting out. But most people don’t understand it’s not temporary. It’s not a sabbatical. It’s not ‘just a phase’.

It takes courage, boldness and lots of planning and sticking to the plan to make that jump and make it work.

I’ve learned to not get too upset when people start questioning and doubting my career choices, no matter how intruding it may feel; unless they are willing to at least try to understand, I simply walk away from that conversation.

May be harsh, but helps my sanity.

My job and my private self start crossing paths

Now, there are many reasons why this happens.

For me, working from a home office certainly doesn’t help divide my personal and professional lives.

Being able to work the hours I choose means I may switch between work and personal stuff multiple times a day if I have to (although I try not to as it makes me less productive).

Running my own show also means that the quality of my work and the client relationships I build directly affect the success of my business… And that may sometimes mean I will be replying to an email far outside of my regular business hours or on weekends, or push a project forward and do it in a shorter timeframe because it will make a huge positive impact for my client.

For obvious reasons, all of this tends to interfere with my personal life, the time I may be spending with family or friends, traveling, or simply enjoying some downtime.

And this proves to be a challenge because of some past struggles. In my most recent full-time job, I used to allow myself to work long hours or look after work from home, on my personal time. After a while, it started being harmful to my peace of mind and it threw off my work-life balance, which triggered anxiety.

When it got so bad that it affected my ability to work productively, maintain healthy human relationships and sometimes even my ability to get out of bed in the morning, I promised myself to never do that to myself again.

That has taught me a huge lesson, and while my self-employed self now is now forever a part of my private self, I am doing the best I can to think of my health, both physical and mental, before anything else.

It’s not easy, but I’m getting there!

What are your biggest challenges of self-employment, especially the not-so-obvious ones? Let me know :)

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Marijana Kay

Freelance writer & content strategist for fast-growing SaaS & marketing brands + Fortune 100s. Obsessed with using content to tell stories. 🇭🇷 in 🇮🇪.