4-day course with Penelope: Get the Guts to Start Freelancing


After a long break from new courses, Melissa and I did a course on how to start freelancing. This is especially timely because over the last six months while I have been rejiggering my online courses Melissa has launched a freelance business.

My first thought was: Oh. Crap. Melissa is too busy to do courses with me. But she says that will never happen.

So join me for Get the Guts to Start Freelancing: it’s a four-day online course with chat and constant chatter from me, and from Melissa who will sometimes moderate and sometimes cut me off to make her own points. You’ll learn how to make a strategy to start and create tactics for attracting more clients as you grow.

This course includes four days of of video sessions and email-based course materials.  You can purchase this webinar for anytime, on-demand access. The cost is $195.

Enroll now.

Do you know why I can live on a farm, and travel to New York and LA whenever I want, and homeschool my kids, all at the same time? Because I’m great at freelancing.

I started freelancing when I kept losing jobs in my 20s. It was more of a safety net than a strategy. But learning to rely on myself as a freelancer meant that as my wants and needs changed through the years I have been able to make a wider range of choices to create the life I want.

I’ve freelanced as a writer, web developer, designer, event coordinator, publicity consultant. I’ve probably freelanced in twenty different fields. The reason I could do that is that I’ve created a freelance system for myself that translates to lots of different industries. And I’m going to show you how to use my system.

It’s true that having a job and collecting a steady paycheck is comforting – I still have fantasies of weekly paychecks. But there is pretty much no way to have a dynamic, growing, engaging career while making family a priority, unless you get control over your own hours.

There are ten million courses about how to launch a startup. I teach some of them. But what I’ve realized is that most people don’t have a startup idea that will get them the life they want. Most people don’t want 80-hour weeks and investors breathing down their throats. What most people want is an interesting life that includes time for paying attention to the people they love. And most of us can get that from freelancing.

What freelancing really is: figuring out where you are most valuable in the workforce and finding the people who pay for that. Freelancing is also building relationships with people who value you for what you want to be recognized for. It’s super-rewarding and it’s the perfect solution for most people feeling boxed in by corporate life.

For most people the barrier to freelancing is they don’t know how to get started. This course will show you how.

Also, Melissa is going to talk about being a freelance recruiter. Her only experience with human resources is getting fired from fifty jobs, yet now she’s making $10K/month working with human resources departments.

Which also tells you that Melissa really doesn’t need to work with me any more. She does it because we have so much fun. And you will too. So come change your life with our online party for the future freelance you.

Day one: Create a path to success that’s tailored to your skills

  • Find your speciaity and tell your story in a way that naturally attracts new business.
  • Learn secrets for presenting yourself in a genuine way to create a word-of-mouth business.
  • Build a plan for freelancing that focuses your time on your strengths instead of your weaknesses.

Day two: How to market your freelance business

  • Identify the clients who will be easiest to reach, and create a plan for getting in front of them.
  • Hear real-life case studies that show how people like you have successfully marketed themselves.
  • Not all marketing is equal. Understand the type of marketing best-suited to your needs.

Day three: Overcome the fear of financial stress

  • All freelancers deal with cash-flow issues. Instead of solving them, learn to work with them.
  • Uncover the freelance-friendly insurance industry – yes, it exists. And find out about companies like Freshbooks that provide financial software specifically for freelancers.
  • Manage your time so you don’t hate your life. You can’t work 24 hours a day. Know when to say enough is enough.

Day four: Q&A

Questions and answers – ask me anything!

So enroll now.

26 replies
  1. Teresa
    Teresa says:

    Thank you for offering relevant and timely courses! I’m getting ready to make the switch to freelance work and am really looking forward to this course! I’m heading over to sign up now!

  2. Darnell Jackson
    Darnell Jackson says:

    What’s up Penelope,

    This sounds really cool

    I have found myself that nothing helps you when you’re starting out more than having confidence.

    The problem is you can’t get confidence until you know what to do.

    You could try to figure it all out on your own but you NEVER know how long that might take.

    It could take years and as a matter of fact that why most people get burned out they get tired of not getting results.

    I recommend everyone who is serious about freelancing get training from someone who knows what they’re doing.

  3. M.G.
    M.G. says:

    Find someone to read your ads for spelling errors and typos before publishing them would also be a good tip.

  4. Scott Asai
    Scott Asai says:

    I love how you have mastered running your own systems and help people get started. You’re so action oriented and give straightforward advice that’s easy to implement (as long as you do it). You’ve figured out HOW to freelance, not so much WHAT to freelance about. Brilliant.

    • Penelope Trunk
      Penelope Trunk says:

      Here’s an interesting thing about introverts. It does not mean a person is shy if they are an introvert. And it doesn’t mean they like people. Extravert and introvert signifies how people recharge themselves and how people process ideas.

      An introvert needs to recharge alone and process before they talk. And extravert recharges by talking to people and an extravert thinks best while they talk.

      So freelancing is great for both types because anyone can market themselves and anyone can make clients love them. It just means you have to know your strengths to do it in a way that makes sense for you.

      And naturally, we’ll cover all that in the course :)


      • Felicia
        Felicia says:

        Thanks for addressing the introvert issue. I am an INFP who has been a freelancer on and off most of my life, and would like to become a self-supporting, successful one going forward (either on my own, or with partners). Do you recommend this course over the course you’re offering on the Myers-Briggs and career? I am on a budget.

      • Peter Belowski
        Peter Belowski says:

        To address the introvert question:

        Yes, you can be a successful freelancer as an introvert. I have done it ridiculously well for 20 years.

        It is difficult to “put myself out there” — it doesn’t come naturally for me. But partnering does. I found what worked best for me was to concentrate on a select client list and build long-term relationships and trust — where I wasn’t successful monetarily unless they were also.

  5. Hossam Salem
    Hossam Salem says:

    I am so afraid to start freelancing because it has some risks of not being a stable income, specially when you want to start a family
    you can’t rely depend 100% on it.
    But maybe i will change my mind soon , a 9-5 job is killing my dreams

  6. Carmen
    Carmen says:

    I’m only leaving this comment here because people keep asking me if they should take this course. My personal opinion may not mean much, but here it is:

    First you have to have a skill that you can market and freelance. If you haven’t learned a new skill yet, then there’s no point in taking any courses until you figure out what skill you want to learn first.

    I’ve been freelancing for 19 years marketing the same skill for 19 years. I want to learn a new skill, something that matches my personality type, and freelance using that new skill. So I took her personality type course first. Now I’m working on practicing my new skill and gaining confidence. I can integrate my new skill with my existing skills in my freelance business.

    That said, I love all of Penelope’s stuff, so if you’ve got a skill to freelance, then take the course. But freelancing something you do not enjoy doing won’t work. Learning something new might be the first step.

    • Felicia
      Felicia says:


      Are you saying you gained clarity about which new skill to offer in the personality type course?

      How did you figure out which skill to use for the 19 years you have been “marketing the same skill?” It sounds like that was BP (before Penelope). If that has enabled you to be successful as a freelancer that is pretty impressive.

      • Carmen
        Carmen says:

        Hi Felicia. I think some of us picked rudimentary skills that we were good at in our early 20’s, and our survival skills have kept us going. I think the need to survive is what drives a lot of freelancers like myself.

        Of course you’re not the same person in your 40’s that you were in your 20’s. You’re more self-aware, and you also become limited in certain ways. Your body can’t handle the same type of stress in your 40’s as it did in your 20’s. So we’re looking for something new out of necessity because we have 30 more years of work ahead of us. There’s no retirement to look forward to, so we’re diving into the next leg of our careers, so I took the personality type course just to gain more insight.

  7. Call Me Carmen
    Call Me Carmen says:

    What a great concept for a course. I have freelanced in the past, but settled into a stable day job for now. But I know life won’t always be this way … nor do I always want it to be.

    Unfortunately I’m traveling that week and can’t make the dates/times. I hope you offer this again later.

  8. ApprentieMaman
    ApprentieMaman says:

    Hello Penelope,
    I have two questions about this course:
    – can it also be helpful for people who are already freelancing?
    -do I have to follow it in real time or is it possible to buy the course and listen to it afterwards?
    (I would prefer the second possibility).

  9. Bjorn Karlman
    Bjorn Karlman says:

    When my wife and I quite well-paid jobs to travel the world and do volunteer work for all of 2013, part of the reason we weren’t too worried we’d be reduced to busking for a meal, was freelancing. It worked. Our freelancing income was definitely a helpful revenue stream. So I am a big believer in what the three-day agenda covers. Here’s my question though: I am Swedish and a lot of the time freelancing gigs seem to favor Americans (a lot of the time companies can’t pay non-Americans easily). Will you address the needs of international freelancers?

  10. hangerart
    hangerart says:

    freelancing gigs seem to favor Americans (a lot of the time companies can’t pay non-Americans easily). Will you address the needs of international freelancers?

  11. Jane Dolan
    Jane Dolan says:

    Great news that Melissa is back on board for this course – she brings a lively & smart element (not that PT is not those things) but the chemistry between the two makes for a super fun seminar.

    As a PT seminar junkie, I can whole-heartedly tell Felicia that you will learn Myers-Briggs AND freelancing. PT loves Myers-Briggs so much that she can’t not include.

    The other thing anyone one the fence should know about Penelope, though she probably doesn’t like the fact out :-), is that she is extremely generous and genuinely wants you to get as much as possible from her courses = she is a fantastic teacher!


  12. New Friend
    New Friend says:

    Hi P. I’m signed up for your Freelance course. Q? From your perspective, what is the diff between calling oneself a consultant vs. a freelance?

    I’m signing up for: Start Your Own Company – as well.

    I’ve begun developing my WP site in preparation for launch as a marketing/strategy consultant – but is it freelance or is it consulting? …Maybe I’ll just have to wait until next week to find out. Cheers! :)

    Love to hear opinions from other posters on this topic. Thanks!


  13. Debasish
    Debasish says:

    Hi….Hope you to be well. Myself Debasish and i am from New Delhi, India. Taking you to my profession i work as a retail merchandiser in a fashion retail brand and now i want with my running job to get involve in free lancing jobs as well by which i can gain little more. So can you please suggest and advice me upon the same so that i can find a track for myself in free lancing. Thanks with Best Regards, Debasish

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