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14 best books to read when you feel lost in your career

Just a quick note that this post includes Amazon affiliate links. If you can, support a local bookshop instead though.

Sometimes you have to feel lost in your career to figure out what you really want. You need to know what feels wrong to work out what feels right.

I fell into the tech world during the year abroad of my English & Spanish degree, and thought that working for a tech giant was what success looked like.

Google and Microsoft rejected my applications, and I ended up working at a startup as a marketer. Then, my idea of success turned into reaching the C-level of a company…. before I burnt out and quit.

I started my own tech consulting and content writing business, did that for a few years, and then realised I didn’t like tech enough to dedicate all my time to it.

Now I write things and share what I know, whether it’s the books I publish, the book blog I’ve built over the last decade, the consulting work I still do 1-2 days a week, or whatever else captures my curiosity.

Along the way, here are the books that have helped me to figure out the way when I’ve felt lost in my career and work.

Some of these are personal growth books that will encourage you to take bolder leaps. Others will help you to question what you really want. A few more are memoirs about people who have found the courage to do things differently.

Read these when you’re feeling lost in your career and, as you do so, ask yourself – what if this is really the beginning of the next chapter of your life?

The best books to read when you feel lost in your career

1. The Big Leap: Conquer Your Hidden Fear and Take Life to the Next Level by Gay Hendricks

The Big Leap is one of my favourite books to read when I know I need to make a big change (and especially when there’s a high chance of me sabotaging my own success).

Gay Hendricks created the idea of the “upper limit problem”. This is about the excuses and sabotages that stop you from reaching the next level in your work, creative projects, relationships, and every other area of your life.

2. Think Big: Take Small Steps and Build the Future You Want by Dr Grace Lordan

Think Big

Think Big is the perfect book to read when you feel lost in your career. It’s all about finding the courage and clarity to dream bigger dreams, set bigger goals, and start taking small but bold steps towards them.

3. Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman

Four Thousand Weeks

Four Thousand Weeks is one of my favourite non-fiction books of the last few years. It asks this crucial question better than any other book I’ve read: what should managing our time actually mean? That and: what should we really be prioritising?

Read this when you’re feeling lost in your career for philosophical food for thought. What do you want to do during your time on earth?

4. A Psalm for the Wild-Built by Becky Chambers

I adore Becky Chambers’ heartwarming, wholesome, and hopeful Monk and Robot series. The first book, A Psalm for the Wild-Built, introduces us to Dex, a non-binary gardener-turned-tea monk on the utopian planet Panga.

Although they love learning about tea and serving customers, Dex still feels lost in their work. So they set off on their bike-powered wagon into the wilderness.

Here, Dex comes across Mosscap, the first robot to emerge from the wilderness for centuries, who’s asking a question that’s surprisingly difficult to get a clear answer on: what do humans want?

5. The Crossroads of Should and Must: Find and Follow Your Passion by Elle Luna

This book is the perfect inspirational read for when you’re at a crossroads or planning a career change. The Crossroads of Should and Must is Elle Luna’s guide to listening to the voice inside of you rather than the opinions and expectations of others.

Whether you’re starting out or starting over, making a career change or a life change, here’s how you can heed the call and act on what you must do, rather than what you should do.

6. The Sun is a Compass by Caroline Van Hemert

The Sun is a Compass is Caroline Van Hemert’s memoir of the 4000-mile, human-powered journey she undertook with her partner, Pat, when she was unsure whether to stay in academia or pursue other callings.

It’s a stunning book that I’ve talked about before, as one of the rare books to really speak to where I am and hoping to go next.

I tried to explain that escapism wasn’t our goal—neither of us was running from a broken marriage or drug addiction or academic failure. We weren’t trying to set a record or achieve a first. We were simply trying to find our way home.”

7. Why We Can’t Sleep: Women’s New Midlife Crisis by Ada Calhoun

Why We Can’t Sleep shares the voices of women in the generation raised to “have it all”… most of whom are exhausted, terrified about money, under-employed, and overwhelmed.

Instead of being heard, they were told instead to lean in, take “me-time,” or make a chore chart to get their lives and homes in order.

In Why We Can’t Sleep, Calhoun opens up the cultural and political contexts of Gen X’s predicament and offers solutions for how to pull oneself out of the abyss – and keep the next generation of women from falling in.

8. The Bookshop on the Corner by Jenny Colgan

Tumble into the pages of The Bookshop on the Corner, a cozy novel about a librarian who feels lost in her career after losing the job she loves.

Nervous but determined and ready for a new start, main character Nina moves to a sleepy village in Scotland where she buys a van and transforms it into a mobile bookshop.

With every new reader she meets, Nina slowly realises that this might just be where she can find a place she belongs.

9. The Enchanted Life by Sharon Blackie

I love this comment in a Reddit thread about the best books to inspire you to quit your job: “The Enchanted Life inspired me quit my miserable f*****g job and work on doing what I love. It’s a marvelous book.”

If you love nature and want to remind yourself of the magic in the world while making big changes in your own life, try reading The Enchanted Life too.

10. Playing Big: Practical Wisdom for Women Who Want to Speak Up, Create, and Lead by Tara Mohr

Written by a fellow quiet person, Playing Big is a handbook for stepping up and being more you.

I first read this book when I was struggling to thrive in an office environment as an introvert. A few years later, I reread it when I started my own business and needed more faith that I could actually succeed.

With this gently inspiring book, Tara Mohr offers such a welcome reminder that you get to choose how you show up. What matters is that you do it, whatever this looks like for you.

11. How to Live by Derek Sivers

Derek Sivers’ book Anything You Want is one of the main reasons I decided to start my own company. It has also informed so much of my business philosophy since then, as well as my book, Simple Business.

However, his book How to Live isn’t just for entrepreneurs. It’s for humans. I love this exploration of living well in which each chapter disagrees with the next.

One chapter makes a compelling argument for why you should be completely independent, keeping all options open. The next chapter argues why you should commit to one career, one place, and one person.

Which one is right? Which does the author believe? All of them. It’s a philosophy of conflicting philosophies. This will also be true for most of us as we move and evolve through life.

12. Mindshift: Break Through Obstacles to Learning and Discover Your Hidden Potential by Barbara Oakley, PhD

If you’re feeling stuck because of preconceived notions of what is possible for you to do and be, read Mindshift.

Above all, it’s a fantastic guide to breaking through obstacles to change direction and achieve bigger goals. But it also reframes seemingly “bad” traits, such as poor memory, impostor syndrome, and getting older into sources of hidden potential.

13. You Are a Badass by Jen Sincero

You Are a Badass

I read Jen Sincero’s You Are a Badass before I quit my job and ended up starting my own business.

It was exactly what I needed: a kick in the butt, but also a gentle touch on the shoulder that said, you can do this.

Read this if you’re feeling lost in your career, or just lost in life. For a boost to your finances, I’d also recommend the book’s finance-savvy sibling: You Are a Badass at Making Money.

14. Freedom Seeker: Live More. Worry Less. Do What You Love by Beth Kempton

Freedom Seeker is another book I loved when I was starting my own business and feeling a bit lost. It’s an inspiring but gentle guide to doing what you love by the author of Wabi Sabi, Beth Kempton.


For more inspiring books to read when you’re feeling lost, complement this with my post on Tolstoy Therapy about the best books to read when you feel lost and directionless in life.

If you’re thinking about starting your own business, even if just on the side of your main job, you might also like my book Simple Business: How to Build a Business for Ease, Freedom & Simple Living.

Simple Business book cover
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