#084: Michelle Ward on How to Make the Leap From Full-Time Day Job to Self-Employment

“How do I successfully transition out of a day job and into full-time freelancing?”

That’s one of the most common questions I get asked by aspiring freelance writers and copywriters.

I’ve addressed different aspects of this question (and suggested courses of action) in a few previous episodes:

#082: Your Biggest Challenge As a New Freelance Writer or Copywriter (and What to Do About It)

#074: Ten Things to Avoid When Ramping Up Your Freelance Writing Business

#048: From Laid-Off Worker to Six-Figure Freelance Writer

#010: How a Well-Paid Executive Transitioned Successfully to Full-Time Freelance Copywriting

#006: How I Took My Writing Biz to the Six-Figure Level (Pt. 1 of 2)

And in today’s episode, you’ll get yet another perspective from someone who’s made the leap successfully and coached many others on how to make this challenging transition — Michelle Ward, a.k.a. the When I Grow Up Coach.

The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe in iTunes or on Stitcher to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

Tell us about yourself

Michelle Ward is best known as the When I Grow Up Coach. When she started as a coach in 2008, she was working as an executive assistant. Before that, she dreamed of a career as a musical theatre performer. Eventually, she became the type of career coach that she needed herself. Today, she provides career guidance to creative women.

How do you advise people who want to go the freelance route?

In brief, you need to start by shifting your mindset. You DO have choices. When you’re stuck in a job, you start to think that this is what work is. It’s what grown ups do.

We’ve all been brainwashed to believe work has to be work—not play.

Suspend your disbelief and ignore the vampire voices in our head. Start by giving yourself a day where instead of listening to those voices, you ask “How?” “How can I do it?” “What steps do I need to take?”

Think about what you can do now, and every day, to bring yourself closer to your goal. You CAN be a grownup and an entrepreneur at the same time.

How do you figure out what actions to take?

The only wrong choice is to do nothing. Doing anything is better than doing nothing. You’ll figure things out when you start doing them. You could think about things for years and never know if they’ll work or not. Get out of your head and into your hands.

Ask yourself: What is the simplest, most cost effective thing you can do for your business that will have the greatest impact. List all the to-dos and prioritize them into “needs” and “nows.” Put aside everything that’s not a “need” and a “now.”

Is there a danger of fooling yourself by taking actions that aren’t getting you anywhere?

You have to be aware. You have to be real. We all know when we’ve crossed the line from legitimate work to procrastination/perfectionism.

What if you don’t have time to build a freelance business?

You’ll never FIND the time. You have to MAKE the time. Go to your calendar and look for things to say no to.

When you say no to things on your calendar, you say yes to your business.

Even if you don’t feel like doing the work, you’ll get into the flow once you dive into it. Try to make it the same day and time every week. Schedule it like a workout

How do you handle client calls when you’re working full time in an office?

You don’t have to explain why you can’t take client calls at certain times. Take the call on your lunch break. Often, clients will assume you can’t take their calls because you’re busy with other clients. It rarely becomes an issue.

Sometimes, you can be honest with clients and let them know you have a full time job. When you eventually leave that job to freelance full time, they’ll celebrate with you.

What can you do if your family isn’t supportive?

Bring your family into the conversation. Ultimately, they want you to be happy. If they’re not supportive, it’s because they’re scared.

Let them know you’re scared too. Share your action plan with them. Let them know what you will have in place before you leave your day job.

Tell us about your course on Creative Live

Michelle’s Ditch Your Day Job course is available on the Creative Live platform. The online course includes about 20 hours of video content, a 70-page workbook and vouchers for Bidsketch, Batchbook and Breather.

Michelle Ward’s website: When I Grow Up Coach.

How David Landed $11,400 in Freelance Work This Summer with a One-Page Sales Letter

I’m doing an online workshop this coming Wednesday, September 2nd on how to land great clients with a simple, one-page sales letter you can send out via snail mail.

As many of you know, direct mail sales letters was one of the key ways I grew my freelance business. And when done right, it’s a strategy that can still work incredibly well today.

In fact, with so much marketing moving away from physical mail and into the online world (via email and social media), there’s a huge opportunity to get noticed when you use physical mail to reach out to prospects.

My guest instructor is a freelance writer by the name of David LaMartina. David has generated $11,400 (and counting) in freelance work this summer by mailing a super-simple, one-page letter to select prospects.

What I love about David’s story is that he’s not a well-known freelancer. In fact, he just graduated from college in 2011, and he’s been freelancing for just three years!

So we’re not talking about someone who had success with this strategy because of his decades of experience or name recognition.

In this class, David will give you the exact letter he’s been using in this campaign. And he’s going to detail everything he’s done, including his exact process, follow-up email script, how he picked his prospects, and much more.

To learn more, visit:


Can’t make it live? Don’t worry. If you register, you’ll get the full recorded replay and all the class materials, including David’s letter.