The Plunge: Keith O'Brien

A self Q&A about my decision to go into business for myself

I realize it’s a bit indulgent to interview myself, but this is a proof of concept for a new, recurring feature. I’d love to talk to you if you have made the plunge (not the leap - because it’s never so graceful) into your own business. Email me at keith if you want to share your story.

Who: Keith O’Brien is me. I am the proprietor and, currently, solo practitioner at Total Emphasis, a content strategy and ghostwriting agency.


Previous titles: Editor-in-chief, Head of Digital Transformation, Head of Content, Director of Media & Entertainment
How long solo: Four years
Where you can find me: LinkedIn, website, here 

Why did you decide to go into business for yourself?

Well, there’s a short, unhelpful answer to that. I didn’t. Being laid off and the beginnings of a global pandemic made that decision for me. I supposed I could have beat my head against the wall and applied to a dwindling number of zombie job postings, but I choose the more likey path. It wasn’t my first time going into business for myself (in between corporate jobs), but I knew that - and I swear this is not a paradox - it would be both hard to get work and, yet, there would be a ton of work out there. High supply and high demand, so it would be who you knew and how you positioned yourself.

What do you do and how do you differentiate yourself?

I do content strategy and ghostwriting for a host of clients. I write anything from social thought leaderships for executives to research-driven reports and whitepapers. I conduct content audits and produce large-scale strategic recommendations. My shorthand: if it involves the written word, I can do it.

I differentiate myself on three specific factors:

  • I explicate how my work pays for itself, both in value to external audiences and the avoidance of requiring much of their executives costly time

  • Prospects they do not need to commit to anything more than one piece of content. Of course, they will get volume discounts if they sign up for more. But I never lose a potentially large piece of business for a smaller, immediate one

  • I reach out to prospects when I am full of business and would struggle to take on their work. It makes the conversation very low stress. But I also tell them they can reach out if they’re in a pinch (writer flaked, client or executive didn’t like original draft) and I’ll get it done, no matter the deadline, no matter what else I’m doing

What do you miss about corporate life?

Not much. I would say I miss being able to go on vacation and having your co-workers cover for you, but that doesn’t really happen, does it? And that’s not an indictment on my co-workers or co-workers, in general. Anyone remotely careerist is irrevocably attached to his/her/their devices and work emails; it never stops. What’s great now, I guess, is you’re getting paid if you’re working on vacation. Pressed to pick something really, the challenges of managing multiple clients can get tricky at times.

What do you love about consulting life?

I love the variety, the problem solving, the independence, the freedom. I love new business, something I thought I would never say. I am the business now, so if anyone is either proactively reaching out to me, or taking my messages, that means they want to be in the business of Keith! That’s exciting and flattering.

What’s your best piece of advice?

Turn off the doubt in your head that stops you from reaching out to someone you think a) won’t remember you, b) is “out of your league” professionally, or c) won’t learn anything from you in a value exchange. Off the back of a pandemic, we are still vulnerable and starved for connection. And we know, we don’t know everything. The person you are scared to contact is scared of something - maybe that exact thing is not being contacted.

Give me three takeaways

  • Love it or hate, LinkedIn is your best friend. Ignore the blowhards and find meaningful connections. Send a message to someone you sort of know but don’t have their email address.

  • Take walks, take deep breaths and tell yourself: it will work out. I am afraid it doesn’t always work out, but I know dwelling on how it won’t work out won’t help.

  • Don’t treat help as a zero sum game. Help whoever you can. Ask for help whenever you need it. It is statistically impossible that it will even out over the course of a lifetime. And that’s okay!

  • Don’t limit to whom you talk. New business is everywhere.

The Plunge

The Plunge is a recurring section where independent contractors/consultants/ freelancers/whatevers discuss why they took the plunge to independence. If you have done likewise and wish to be featured in an upcoming piece, email me here.