Climbing The Ladder

How To Actually Go From “Aspiring” To “Professional”

By | Monday, March 07, 2016


Over the weekend, I got a question in the Ask Chelsea Anything inbox that touched on something we’ve talked about a few times on the site, and which I think is always incredibly important — especially given how much we advocate the hustle economy and the always-having-a-side-project lifestyle. The reader wrote,

“So, after years of wanting to become a freelance writer, I’m now finally starting to take tangible steps to get it all happening — I’ve started my writer website and plan to start uploading blog posts to it shortly. I plan to contribute articles for free to various sites to build a portfolio and am fully aware that I may be doing this for a while before I’m qualified to start charging rates.

I guess I’d love to hear your opinion on when you think it’s best to actually start charging money, and how to start negotiating a fee when you’ve been contributing to a certain site for free. How many published articles should a person have to their portfolio? Or, is it more a case of contributing a certain amount of articles to one website before it’s fair to even ask the question?”

I have tackled this question to some degree specifically from a writing perspective, because that’s what I’m obviously most qualified to talk about, but I think there are some universal truths when it comes to making that transition from “amateur” to “pro,” regardless of industry. (Even for things that aren’t freelance-based, there is the internship-to-employee pipeline that can feel like you’re on a hamster wheel of never quite being taken seriously.)

The overarching issue here, I think, is a philosophical one. It can be very hard to take oneself seriously in an industry one is trying to break into, and as someone who spent nearly an entire year writing on a near-daily basis for free, I can attest to just how difficult it can be to ask for money. But as with many things, professional evolution is often a “fake it before you make it” concept, and unless you start considering yourself as a professional and acting like one — in negotiations, in interviews, and even in in emails — you are never going to become one.

This is why I feel, if you are about to do work for someone, whether that’s a one-off project or a full-time internship, you must always ask for money. Even if you are fully prepared to do the work regardless, you need to make sure the topic of money is at least broached. Let them know that it’s on your mind, and that you are not just some wide-eyed youth fresh off the bus, eager to help out.

Make sure that your LinkedIn, email address, email signoff, social media profiles, and business cards are all reflective of what you are doing — even if that work is for free. Put every effort into portraying yourself with the seriousness with which you need to be taken, and never downplay your accomplishments. Always tell the truth, of course, but put your successes on display and craft your image thoughtfully. If you’re going for an interview, dress like a future employee, not like a future unpaid coffee-getter. These are all superficial changes, to a degree, but it is our appearance and presence which will often make the difference in a job, or a rate, or even a salary. Build this with attention to detail.

Similarly, your portfolio and personal site or blog (and nearly every career track could benefit from you having one or both of those) should always be as up-to-date and impressive as possible.

Ultimately, the truth is that the timing for “when to ask for money” is “from the beginning.” The timing for “when to negotiate” is “as soon as any money is on the table,” (and I lay out some specific strategies for negotiation in the article linked above). But the more nuanced question is “when to walk away if money isn’t there,” which is something we all have to navigate for ourselves, based on a huge number of factors (financial security, job aspirations, level of competitiveness of our industry, etc). There are many people in my industry, and I’m sure many others, who get quasi-religious about the whole “never do any work for free” phenomenon, but I think this is shooting yourself in the foot at the very beginning of things. For me, it’s more about “when and how to stop working for free,” and to be clear, I still write for free for certain projects when it has some other, tangible benefit for me.

Knowing when to walk away is a tough thing, but it’s important that you accept it for a variety of reasons. Maybe you’re in a string of unpaid internships that aren’t leading to anything bigger, and need to start switching career tracks. Maybe you’re writing for a publication whose byline you’ve secured, but aren’t getting any money from. Maybe you’re gifting samples of your Etsy line to an influencer and aren’t seeing the customers trickle in from it. Whatever it is, learning to say “no” and mean it is the biggest hurdle. I’ve had many clients come back after I say no to a certain rate, and give me what I was looking for, because the truth is that the strongest and most influential negotiation tool is being able to walk away. If negotiation were quidditch, walking away would be the snitch. Everything could be going perfectly, but if someone plays the walk-away, everything can flip in an instant.

Going from an “amateur” to a “professional” whatever-you-are will be a very different path for everyone, but there will always be key consistencies: professionals take themselves seriously, they curate their digital-and-IRL images, and they never let the topic of money go undiscussed. They know when to walk away and have done it, and they know that for every 10 rejections they face, there will be a success that makes it all worth it. They know that these things happen incrementally, and that only you can push that notch forward, because no one else will do it for you.

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