Falling Off The Ladder Book Review: A Freelancer’s Perspective

Falling Off The Ladder book on a blue wooden background

There’s been a lot written about the practical aspects of starting a freelancing career. How to set up a profitable freelancing business, how to market your brand, how to manage your finances. But what about the mindset needed to thrive as a freelancer? That’s what this review of Falling Off The Ladder by Helen Hill aims to discuss.

Falling Off The Ladder book on a blue wooden background
Falling Off The Ladder: Revamp your mindset and thrive in self-employment

Note – Kate received a copy of Falling Off The Ladder as an early reader. However, Kate was not incentivised in any way to influence her review.

Key Takeaways:

  • It’s an honest take on what it’s like to make the jump to self-employment
  • You can learn from the author’s experience with tough times, learning to say no, and various other challenges
  • I found myself reflecting a lot on my own freelancing journey as I read it
  • It’s the perfect read for anyone thinking of leaving full-time employment to start freelancing

Who Is Helen Hill?

Written in a friendly, reassuring voice, Falling Off The Ladder is packed with useful advice about making the move from a traditional career path to self-employment.

Helen is a freelance digital learning and content design expert. With 13 years of industry experience, she made the move to self-employment in 2018. She wanted to share her experience to help others following a similar path trying to find their feet in the freelancing world. So it’s a very fitting book to review on the Freelance Ready blog!

What Is Falling Off The Ladder About?

Falling Off The Ladder is a guide to developing the mentality needed to thrive in self-employment. It looks at how to succeed (on your own terms), find fulfilment in your career, and navigate the highs and lows of the freelancing journey.

People ‘fall’ off the traditional career ladder and into self-employment for many reasons. They may be looking for a job that better suits the demands of their personal life. They may have experienced a toxic work culture or burnout. Or they might simply feel the traditional ladder wasn’t for them. In the first few chapters of the book, Helen explores these reasons in more detail.

In part two, she looks at the five stages of deciding to become a freelancer. The panic at the disco stage in particular may sound familiar to anyone who has already made the leap to freelancing!

The rest of the book then focuses on the benefits of self-employment, as well as how you can deal with the inevitable challenges that you’ll face. This can serve as a super useful primer for anyone looking to make the jump to freelancing, or that has recently done so.

Why I Loved This Book

This isn’t a book to just read once, put back on the shelf, and never look at again. There are interactive activities at the end of each chapter to help you reflect on the key issues and questions raised. This turns the book into more of a journaling exercise that helps you examine your own purpose and reflect on your motivations for going freelance in the first place.

One of the things I enjoyed most about the book was its honesty and practical advice. Hill doesn’t shy away from talking about the challenges of self-employment. Whether it’s lacking motivation or confidence, having blurred boundaries between your work and personal life when working from home, or just the ‘feast or famine’ nature of freelancing. We all know it can be hard at times!

Helen discusses all of these issues (and more) and offers practical advice about how to manage them. For example, she suggests keeping a “little book of epic wins,” in which you write down your achievements and revisit them when your confidence takes a dip. The experiences and advice of other freelancers are also woven throughout the book.

This helps bring a multidimensional perspective to everything covered within it. It doesn’t just make it actionable and practical as a freelancing guidebook, but it’s also just a damn good read!

Who Should Read Falling Off The Ladder?

This book is ideal for anyone who has recently made or is thinking about making the leap from traditional, full-time employment to self-employment. It’s especially timely given that the COVID-19 pandemic has reshaped the employment landscape, as well as many people’s career expectations and aspirations.

Editor’s Note: This is true even in 2023 as I update this post, with the effects of the pandemic very much still apparent across the freelancing industry.

Reading Falling Off The Ladder will help you decide whether freelancing is right for you and equip you with the mentality you need to succeed. It’s the first book I’ve come across that talks about this very important aspect of becoming a freelancer. I learned a lot from it and found it both reassuring and motivating!

It’s Useful For Beginners & More Experienced Freelancers

The book is an equally helpful resource for more experienced freelancers who are having a wobbly moment in their career. The exercises prompt you to reflect on your freelancing journey, the benefits it offers, and your values. This can be a useful reminder when you’re feeling frustrated or burned out by self-employment.

Overall, Falling Off The Ladder is an invaluable guide on how to thrive in your freelancing career!

Note: For another review of a great freelancing book, check out Kate’s article on The Multi-Hyphen Method by Emma Gannon

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