From Freelance Writer to Boss

Once upon a time, I was a freelance writer but it didn’t stick.  I’m watching another friend struggle with the tipping point right now. She’s too big to be her one woman show freelance micro-business (graphic and web design) anymore, she can’t keep up with all the work. She’s either got to start turning down work (and keep that super annoying late night part time job OR price herself much higher in her uber-competitive market where her established niche is affordable for micro business). The other option is to take that leap from Micro to Small business – and get some contracted or employed help.
I remember being a solo flying freelance writer and copywriter, making enough but not a lot. There comes a tipping point where you have to decide if you want a growing business or to remain a freelancer. It’s daunting. It’s terrifying. It’s freaking hard. I’ve watched closely as two businesses have taken the leap and have worked with dozens of others. Here are the challenges you’ll likely face going from freelance to boss!

Freelancer to Boss - the Talk About Creative team being photobombed at Ric's Cafe last year

Leaving the freelance market means putting prices up

You’re going to have more unbillable hours shortly, you now need to cover them. Remember if you’ve always been “affordable” as a point of difference, soon you’ll be slightly less affordable but you’ll be able to meet deadlines better, offer more choices, offer different skills etc. That’s worth a bump in price. You may find that putting prices up brings more customers and better quality ones. I did.

You don’t need employees right away.

If you’re a service, there are usually plenty of freelancers looking for clients so you can easily work with them to pick up your slack at first. It does mean sharing your clients and proprietary information with a potential competitor – putting you out there in terms of risk. It’s vital to get a nondisclosure agreement and contract organised that stops them from contacting your clients directly and keeps your trade secrets, well secret. If you’re an online store, just needing help with picking and packing, it’s time to put feelers out for a local lady looking for a few hours. Friends can get complicated but if you’re in a local social network you can put out feelers for some contract casual help. They’ll need an ABN and some flexibility. The problem here is that you’ll train them up with no guarantee they’ll be sticking around! You trade all these disadvantages for the advantage of being able to grow at your own pace without tying up money and risk in employees.

Contractors are human

One mistake I’ve made and have seen others make is to assume that you’re paying them, therefore they must be perfect. Nope. Contractors are no different to staff in that you’ll be dealing with a human being who has talents and flaws, dramas and complaints, who will make you feel better and worried…. It’s just like managing staff! You’ll need to pay close attention to your freelancer’s gifts and flaws and be sure to get them working to their strengths…even if it means you do a particular job you hate because they’re not great at it!  After I contracted my own freelance writers, I was still stuck with the task of blogger outreach because NOBODY did it well.  Luckily,  freelance writers by the name of Amanda and Dani came along and saved me from this dreaded task but it took a long time to find people good enough.

Your mark up on their work

Not marking up enough is another biggy! If you’re hiring at $20 an hour and charging the client $22 you’re going to make a loss. With more help comes more unbillable hours. Way more. And eventually, you may need more team members on unbillable hours like book keepers and admin. If you charge an hourly rate for your work, this is where it’s going to get tricky as the freelancer needs a competitive hourly rate or they’ll leave you for someone else. Your client needs affordability but if they’re good, loyal clients, you might find it doesn’t matter. One mistake I’ve seen made is to use far flung freelancers from Elance or Odesk. This can work. Maybe they can do some of the work to keep your costs down, but you run the risk of reducing the quality of the work. If you then decide it’s not working and try to put your prices up, the clients are going to bolt! If you are using developing work workers, screen them first!

You are not responsible for the whole wide world

Hiring friends muddies this one. Hiring contractors does give you the benefit of being able to… fire contractors. Unlike employees, the contract you have will likely have an easy peasy get out of the contract free clause. This means that when someone constantly misses deadlines due to personal drama, you can just stop working with them. Easy peasy, right? Actually firing contractors makes you feel like a giant lump of poo. It will tear away at your soul and make you feel like you’re responsible for their children’s Christmas and their mortgage payments all in one. You’re not. That doesn’t help. You’ll still feel like poo. BUT legally, you can do it, and you WILL have to do it.

Freelance writer training – what I did wrong

Training is one mistake I’ve made several times. I have “thrown them in to sink or swim” traditionally and done training via feedback and edits. NOPE. One round of training changed the way this business works. The change in culture and the confidence was an epic shift for the better. Make it fun, make it valuable for them, bring cake – it will double as a team building exercise done right. Upskill them. Find out what they’d like to be doing in the business and teach them – even if it’s a job you usually do and enjoy, they can do and enjoy it while you take a holiday (yes, once you make this move, you can have holidays and still make money). If they enjoy working with you and feel like they’re growing their skills and are part of something they enjoy, you will end up with a loyal, happy team….even if you can’t afford to pay them what you’d love to pay, or give them the benefits that they’d love, or make them bona fide employees. This is about empowering people to grow their own careers…you owe it to them!

Going from a humble freelancer writer to a boss was incredibly daunting.  If you’ve limited managerial or business experience – be honest with them, show them that you’re learning the ropes too. Be patient and remember that you need them as much as they need you and bam, you’re suddenly in small business!

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