“Surround Yourself With Positive People:” Advice From Writing Coach Rebecca L. Weber

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By Susan Johnston Taylor, Freelance Writer

Speaking Out Loud

Rebecca L. Weber’s freelance writing credits read like a who’s who of consumer journalism: The New York Times, USA Today, The Washington Post, and CNN Travel. She also does content marketing for nonprofits and associations.

Born and raised in Boston, Weber has reported stories from four continents and is now based in Cape Town, South Africa. When she’s not reporting on travel, social justice, and other topics, she coaches emerging and mid-career freelance writers and recently launched The Writing Coach podcast.

We skyped with Weber to get her insights on freelancing, where writers falter, branching out into podcasting, and more. The following conversation has been edited for clarity and brevity.


The Beat: What do you love about what you do?  


Rebecca L. Weber: The thing that I really like about writing and coaching is that there is this chance for exploration of things that I'm really interested in. Particularly with freelance writing, I have been able to take my own mini obsessions and questions that I'm curious about and pursue them to write about them for other people.

I am really genuinely curious and interested in the writing and creative process so I get to explore that a lot in the coaching as well. I’m trying to figure out what can be done so that people can also explore their passions and help them get out of their own way.


Is there a recent project that you're particularly proud of?

I just started The Writing Coach podcast, and I write the episodes out, first. It's sort of a hybrid of a number of different things I've done in the past. Part of why I'm proud of it is because I had to overcome my doubts and insecurities about my voice, about speaking out loud. "Is anybody going to want to hear me in their ears?" kind of thing.

My writing is normally for a client. We get very clear about what they want beforehand, so this was really my having to identify, on my own, what I think people are going to want. There's been a certain amount of self-coaching through the process to make sure the editorial content made sense and the listener would find value in it.


What's the biggest obstacle you've overcome to get where you are?

There's one obstacle that recurs in different ways: Self-doubt, needing to find again and again that purpose of going forward and recommitting again and again.


What are the biggest mistakes that you see in writing colleagues or people that you're coaching?

I see a false belief that I think a lot of people have. They think that when they achieve a certain external goal, all their self-doubt and insecurity is going to fall away. They're looking for external validation. They’ll get those certain assignments, or hit a certain income level, or some kind of external goal – and it doesn't happen that way. So that's not exactly a mistake but maybe a mindset issue.  


What are some of the misconceptions you see around freelance writing?

Some people just don't understand all the different parts that go into it. They think that you're just reporting and writing when actually you're also running a small business. You have to deal with the marketing and invoicing and figuring out what's going wrong with your Skype. There's not an IT person for me to call, I'm going to have to figure that out. There are just a lot more pieces in motion to the final product that other people see. There are parts of it that are easy and there are parts of it that are really fun and rewarding in their own right. But I think that people underestimate how much non-writing there is to be able to sustain yourself as a full-time writer.


What is the best and worst writing advice that you've been given?

The worst is at that you've always got to do the same exact thing again and again. I don't think there is one simple way that works for everybody. There are a lot of things that work for a lot of people and you also have to experiment and see what works best for you.

I suppose the best advice is to not be afraid to go deep, to be willing to explore ways of writing and topics that aren't necessarily obvious.  

Is there anything else that you’d like to share?

Find other people, other writers, who are supportive of the kind of work that you're doing, who can be role models for you, and who can be supportive peers who are either at your level or what you're aspiring to do. That can be super useful in those times where you're hearing those clichés about how there's no money in freelancing and you can't make a living off writing. There are so many people who are. Surround yourself with positive people who are actually doing it.

Listen to Rebecca’s podcast, The Writing Coach, for more tips.