Don’t Just Survive Your 1st Year Writing Online. Nail It, and Prove Everyone Wrong
You’ve hired yourself, now what?

Maybe mum was right.
Maybe the HR also had a point when they said why don’t I just take some time off.
Maybe I should’ve listened, taken a few hikes through the woods, or swam in the Caribbean Sea for a few days, and then gone back to the safe paychecks. I miss those a lot.
What the hell have I done?
Your only certainty
No matter how strong your creative pull is, no matter how much of a safety net you’d built before you left your job, or how enthusiastic you felt about your new freedom, there will come a time of serious, all-consuming, hair-pulling self-doubt.
In fact, it will probably come much sooner than you think.
This is believed to be one of the biggest reasons why the most likely time for people to return to being employed is within or shortly after their 1st year of working for themselves.
For some people, this might in truth be for the best.
For others, writers and creatives in particular, the idea of going back to safety will be more suffocating than sitting in a sauna full of strangers.
If that’s you, here are a few survival tips I’ve learned on my 2,5+ year journey of making money writing words, that have helped me outlast all of my doubters’ expectations (and mine too):
This is the most serious promotion you’ve ever had
The reality is:
Not only you’ve just hired yourself. You’ve promoted yourself to a position that would otherwise take you years to reach. You are now the CEO. The founder of the venture that’s going to make or break your career.
Take this promotion more seriously than any other promotion you’ve ever landed in your life.
Respect yourself as the CEO. Nurture yourself as the creative brain. Educate yourself as the marketing force.
During your first year, you’ll need to wear multiple hats, probably many more than just the above three.
Set up a strategy map (mine is a boring Google sheet) to iterate and review weekly and quarterly, to stay clear on how you’re managing it all.
You’ll need to make peace with unpredictability and flexibility and be willing to jump head-on into the kind of mud you would never consider jumping in at your day job. Pig-play-pen level kind of mud. Only, you’re not just playing.
Things are about to get just as rough as they are exciting.
First, find your feet:
Ideally, you’ll have built a safety net on which to live for a while (heavily recommended).
That gives you a bit of time for maneuvering trial and error.
Use this time to:
BE a beginner
Give yourself the space to be a newbie. Learn as much as you can from it. Even if you’re not new to writing itself, building a small business based on it is of course complex, and in so many ways not about writing at all.
You’ll need patience and courage. Bucketloads of it.
Adjust to your new universe by scrutinizing what other people are doing, learn all you can from (legit) creators online, get started on building a network with other people in your niche.
Set up your daily routine. Try different things until you find what really works for you.
At my leaving party, which started at the office and then swiftly moved to a grungy pub on York Way, a few colleagues said the exact same thing to me:
“Good luck to you, but I couldn’t do it. I need the discipline. I won’t get anything done otherwise.”
And they were right. Discipline is everything. So you need to wear your CEO hat strictly at all times.
But always remember, no one starts off being excellent.
You’ll make mistakes, feel far behind everyone else, fall asleep at the desk from not having a break for days, drink too much wine. That’s fine.
Allow yourself to be human.
Find actual work
Maybe you already have connections you’re bringing from real life to build on.
But if you’re truly starting from scratch, everything is good enough. Even Fiverr and Upwork. The two are excellent for finding entry-level writing gigs to build a portfolio.
Get ready — you’ll be making lots of submissions and pitches and only a few of them will stick at this point. But as you build, your success rate will increase, and with a bit of luck, increase fast.
Golddust:
- Clients looking for long-term collabs.
- Writing gigs about topics you could talk about in your sleep.
- Clients previously let down by the quality of someone else’s work. Do a great job and you’ll shine!
Any unique skills you could use?
Maybe you have an extra-superb eye for detail (editing gigs), speak another language (translating gigs), or are great at catchy one-liners (email marketing).
Explore as many options as you can to see where you stand out.
Blogs currently accepting pieces from new writers:
- Listverse — fun listicles. You get paid $100 for each accepted listicle.
- Cracked — humor, personal experiences, pop culture. They pay up to $200 per article.
- Funds For Writers — writing career advice blog. Pays $50 per original piece and $15 per reprint.
- Reader’s Digest — will pay you $100 for sharing a personal story.
- Copyhackers — copywriting tips. They pay $300 — $1000 per accepted guest post.
- Eating Well — all about healthy eating. Pay rate is $1 per word.
The only way to tie it all together
On those agonizing days I try my hardest to remember this:
Pain is the price for pushing through plateaus. Discipline guides you through that pain.
Discipline sounds hard and restrictive, and like it’s exactly the kind of thing you’d wanted to escape when you left your job.
But discipline has this unique beauty about it.
It lifts you up and pushes you forward through pain, and it also drags you back down to earth when you’re too high on success.
It keeps you working, cool-headed (for the most part), and level. You stay steady. You make less impulsive mistakes. You keep going, building the habit, stretching the writing muscle.
You can keep things as balanced as you need. Keep your mornings disciplined, afternoons flexible. Or vice versa, whatever works. It’s not about restrictions.
Rather, it’s about respecting your inner CEO enough to do the things you said you were going to do, when you said you were going to do them.
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More useful stuff published (now weekly) on my Substack: Building Momentum, Solo
