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The Power of Starting Something Stupid. These People Did It, So Can You.

From the start of my freelancing entrepreneur journey, books and blogs have been the source of all my inspiration and motivation.

When we are stuck in a conventional life, surrounded by other people doing conventional things, we naturally think that “this” is just the way life is.

But once we’re introduced to someone doing something different or a book that shows us a different way to live life- it’s hard to go back to living average without desiring something more.

The Power of Starting Something StupidAmong the many books that have influenced my journey recently is “The Power of Starting Something Stupid” by Richie Norton.

The premise of the book is that the most life-changing technologies, businesses, and success-stories started off as a conventionally stupid idea. And that to really live a happy, fullfilled, authentic life, we need to act on our “stupid” ideas.

Richie Norton shows the reader that we must learn how to crush fear, forget procrastination, make no excuses, end pride, and be authentic with our “stupid ideas”- wrapping this all into what he calls the New Smart.

So when thinking about the Freelance to Freedom Project tribe (that’s you!), I thought you might be able to use some motivation from other people who have done stupid things and are grateful for having done so.

Life’s too short not to start something stupid. Tweet that!

So I reached out to some awesome people and asked them to respond to one question:

What is one conventionally “stupid” thing you did in your career without which, you wouldn’t be where you are today?

And here’s what they had to say:

Corbett Barr- The Man Behind Think Traffic

Corbett Barr

I left my safe and prestigious consulting job to start a business. At the time (in 2006), it was conventionally “stupid” to leave a comfortable and high-paying career for the uncertainty of a startup. If I hadn’t made that leap, my entire life would be so much different than it is now. I’m so glad I ignored the conventional advice.

Paul Jarvis, Author of Be Awesome At Online Business and web designer @


I quit making websites for professional athletes in the NFL, NBA and NHL.

On the surface it sounds like a dream job. I got to go to any games I wanted and travel to see the playoffs in person. The only problem was that I really don’t like pro sports. Leaving clients like that behind was the best thing I did because it opened myself (and my schedule) up to take on work I actually enjoyed doing and allowed me the space to take on projects that were a better fit for me personally. Now I have a career I don’t hate, because I built it on my own personal values.

Rebecca Merrifield, Marketing Maven @ The Marketing Movement

Rebecca MerrifieldI turned up to a job interview for a marketing position in March and told the interviewer (the CEO) I didn’t actually want the job (a full-time, perm position) but that I would be a Consultant for them instead and proceeded to tell him all the reasons why that would be more beneficial for his business. The result- I got my first consulting gig, which has paid the bills, given me a higer level of experience and has allowed me time to work on my online business as well!

Tom Ewer, freelance writer and blogger @ Leaving Work Behind

Tom Ewer

The conventionally “stupid” thing I did without which I wouldn’t be where I am today was quitting my job when I was only making a few hundred bucks per month. My outgoings were more like $3,500 per month and people thought I was crazy. However, I did my best to remove emotion from the equation and objectively and quantifiably assessed my chances of building up a sustainable income over the following six months or so. Fortunately my calculations were correct and now, nearly two years later, I make far more than I ever did in my previous job!

If I hadn’t taken the plunge then, I’d probably be far behind where I am now (or possibly still even in my job).

Rebecca Tracey, Life-Switch Coach + Professional Adventure Instigator @ Uncaged Life


Rebecca TraceyWhen I started my business, I immediately bought a van and went on a 7 month rock climbing roadtrip. They say a new business needs your full time attention, and I was only able to give it my very part-time love. And it worked! It gave me the time explore different ways of working with people, it let me try out location independence and see how I liked it, and it took the pressure off of having to make everything work NOW. I wouldn’t recommend everyone do this, but it certainly taught me many business lessons that I wouldn’t have learned had I taken the safe route!

SarahXO, circus performer, blogger and freelance web designer @ SillyGrrl


The conventionally stupid thing I did was leaving my job with a mortgage to pay all on my own. Most people would probably call that crazy, but if I wanted to escape the cube and work for myself I had to cross my fingers and just go for it. Couldn’t wait for anyone else to help me out!


Amanda Aitken, psychic brander, incurable creator and the founder of The Girl’s Guide Courses


A couple of years ago, I turned down a book deal from a major publisher. After finding me through my online course, The Girl’s Guide to Web Design, they wanted me to write a book aimed at beginners to web design. At first, this sounded like an incredible opportunity – but I had SO many exciting plans for how I could better serve and teach my students that year…and I just didn’t feel right about spending my time writing a book that was “just” about HTML and CSS. My mission is much deeper than that – I’m here to empower women to wake up to magical new possibilities by expressing themselves and launching businesses online – so I said “no” to the deal. I don’t regret it for a minute!

Heather Thorkleson, Bullshit-slaying life & biz strategist @

Heather Thorkelson

Back when I started working for a big pharma company, the only reason I was there other than to pay off university debt was to potentially be eligible for a Global Health Fellowship (6 month paid fellowship in a developing country) down the road.  The caveat was that I needed to put in 5 years with the company to be eligible.  So when the Director of Sales asked me at a nationwide meeting, two weeks into my contract, where I saw myself going with the company, I said, “I want you guys to send me on a Global Health Fellowship if I’m still here in 5 years.”

Cheeky?  Maybe.  He was taken aback, and my co-workers who overheard were horrified because the economic climate at the time made most people bend over backwards to please ‘the company’.  I was like some kind of brazen loose cannon in their eyes.  But 5 years later, I sent an email to that same Sales Director and said, “I’ve been accepted for a position in Cape Town and I need you to sign off to make it happen.”  He signed, congratulated me on my tenacity, and I went to Africa for 6 months.

Nobody, not one single person, thought it was a good idea for me to tell the company I expected something back from them beyond my salary.  But to me it was a no-brainer.  And my work in Africa was precisely what led me to the realization that I could never do work again that wasn’t directly in service of others.  It altered my heart fundamentally. It woke me up. I left the company a few months after my return from Africa and now I spend every day all day helping people.

Shenee Howard, business activator and brand creator @ Hey Shenee

Shenee HowardI launched my first course on a list of under 120 people. It was January 2012. I knew I needed to do something DIFFERENT but I wasn’t sure what to do and I knew teaching was something I could be good at. Everyone told me that I needed at least 1000 people on my list to launch a successful class but I sold out that one and every one since then and I JUST got my list over 1000 a few months ago. You can’t wait for other people to tell you it’s the right time to do something. Sometimes you just gotta do it. What is the worst that could happen?

Dave Conrey, No B.S. straight talk approach to creative pursuits @ Fresh Rag

Dave ConreyI think “conventionally stupid” is relative to the people on the outside looking in at our actions, so I rarely think in terms of what would be considered foolish by others. That said, I think the most profound thing I’ve done that most people would call stupid is when I shared a post on my blog entitled, “I am Unemployable”. It was a post dedicated to the idea that I was eventually going to leave my corporate 9 to 5 job as a magazine art director, and venture out on my own to pursue my passion of helping creative individuals grow their business. If anyone from my company had read that post (and I’m sure some did), they would have called me dumb and/or crazy because it was a sure fire way to get myself fired. I didn’t get fired right away, but the post changed my mindset, and I spent the next 3 months wondering how much longer I would put up with the crap at my job. Then one faithful Monday, I got the pink slip I wanted. I was laid off after 10 years with the company, and it was the best (and scariest) day of my life. I wouldn’t be where I am now if I hadn’t written that post.

Christie Halmick- Creative courses for the DIY entrepreneur  @ Jewels Branch

Christie HalmickI left my job as art director of St. Louis’s premiere bridal and tourism magazines. A few months before I left, I’d successfully negotiated a 40 percent salary raise for myself and got the go ahead to hire an assistant. I had no plan of what I was going to do next, very little money in savings, and my husband was in the early startup phase of his own company at the time. I wouldn’t be running Jewels Branch today if I hadn’t walked out that door, though.

Nikki Elledge Brown- Communication Stylist @ Nikki Elledge Brown

Nikki Elledge BrownMy big, life-changing, biz-launching offer was a secret when I first announced it – even to me.

It was LATE on a Sunday night. I’d just gotten home from a weekend visiting my great aunts and uncles. I decided to announce in Marie Forleo’s Facebook group that I was going to share an “Exclusive Marketing Week Offer” with my email list that week. I really didn’t know what that exclusive offer would BE when I first mentioned it. I just felt like it was the right time to put myself out there.

The next day, I called my sister to ask, “So what should the offer BE?!” I remember scribbling notes in my planner, trying to do the math on what my “hourly rate” would come to. I’d had just two clients up to that point (in my first weeks of business). I knew I wanted to work with MORE clients, but I didn’t set a sales target of any kind. I just decided on the offer, then shared it via email throughout the course of the week.

The rest was craziness.

In the three weeks that followed, my client list grew from 2 to 92. And (thankfully) it’s been growing steadily every since. It’s that “secret” offer that changed everything. No goals or expectations, just a word nerd looking to be of service.

Moral of the story: Don’t overthink things! Go with what feels right, and share it with confidence. The right people will LOVE it.

Lauren Lund, web designer @ Code Culture Inc

Lauren LundI quit my high paying design job (that many people would have killed for) in order to start my own web design business. I barely had any clients lined up or money in the bank, but I knew I’d do anything I had to do to make it work – I couldn’t stand the thought of spending one more day working for someone else! It was definitely a huge risk but I’m happy to say that it’s all paying off. My company, Code Culture, is officially incorporated and I’ll be hiring 2 employees to help me keep up with the workload this fall.

The best part of being my own boss is the mobility that it provides – especially when working online. As I write this I am sipping a coffee on a patio in Vancouver. To my left are mountains and to the right, the ocean. Definitely beats the cubicle I used to work in.
When I first quit my job, many people thought I was doing something “stupid”… Now, they’ve never been happier for me. If you believe in yourself and your ideas, and you’re not afraid of hard work, you can make it happen too!

Chris Pearson, the man behind Thesis @ DiyThemes

Chris PearsonI stopped building on a VERY successful platform and developed a new one (for 2+ yrs!) to prepare for the future.



And of course- Richie Norton himself, author of “The Power of Starting Something Stupid”

Richie NortonMy life has been a series of making “stupid decisions” which turned out to be smart choices. One of the so-called stupid decisions I made early in my career was to pursue a dream to help budding entrepreneurs in developing countries. I had no time, no experience and no money to make this dream possible…I was still in college trying to get my feet under me. I entered a business plan competition with the idea and it completely failed. However, I moved forward anyway despite the naysayers. Through a process of getting mentors and partners I was able to successfully launch a mentor-venture capital company before I graduated and help people start companies in developing countries. This “stupid idea” became a catalyst for many opportunities including consulting, new ventures and eventually writing “The Power of Starting Something Stupid”. Leaning into stupid was the smartest thing I could do for my career.

So, what stupid idea are you going to start?

Now it’s your turn. In the comments below tell me what conventionally stupid thing have you done, without which you wouldn’t be where you are today?

Know someone that could benefit from a little motivation to start something stupid? Share this post!



Leah Kalamakis Leah Kalamakis is the founder of The Freelance To Freedom Project and a web designer/developer for brilliant entrepreneurs. When she’s not hanging out in the FTF Community, you can find her people watching on the streets of NYC. Come say hi on Twitter, Instagram, or Facebook.

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{ 29 comments… add one }
  • Great post Leah and thanks so much for including me. I love what Amanda said about choosing to do what really lights her up instead of what looked like a good idea on the outside. And also Shenee’s comment about launching to a small list. I launched my first Adventure Reboot to Iceland when I only had 128 people on my list and within 2 days all four spaces had filled (it cost $1700 not including airfare). It’s not always about the numbers! It’s about the value you bring and how Your People perceive you. Forget about what Everybody thinks – they’re not Your People.

    SO FLIPPING EXCITED you’ve launched Freelance To Freedom – this is so needed! Congrats!

    • Leah Kalamakis Leah

      Thank you Heather for being an integral part of getting this off the ground and of course contributing your story for this post. People need to hear these things to help get over their fear and make the jump! Love that about your retreat and another great example of what Shenee spoke about regarding list size!

  • ahhhh thank you for posting all these FANTASTIC entrepreneur experiences. I think I quite like starting something stupid 🙂

    • Leah Kalamakis Leah

      Yes- and there are some more great examples in the book.

  • Hey Leah. My situation is a bit different. My corporate jobs are ancient history–back in the 90’s (gasp!). I had been happily doing the stay at home mom thing for over a decade. I was blessed with a comfy life and a wonderful family. But it wasn’t enough. Many of the mom’s in my community looked at me funny when I started my business. They wondered why in the world I would want to work. But I do want to work and even if it seems stupid to some, I want to make a difference in women’s lives and the more people I can touch the better. So stupid or not, I am all in–and super happy. Thanks for this great post. I love reading about everyone and their journeys.

    • Leah Kalamakis Leah

      Thanks for the story Lorna! Yes- starting something stupid isn’t about quitting but about doing what’s right for you regardless of what others may think. Congrats to you for doing what is fulfilling and makes you super happy!

  • I love this and appreciate you putting it together in such a creative way. That book is being added to my “must read” list!

    • Leah Kalamakis Leah

      Thanks Krista! There is still 2 days left to enter to win a copy!

  • I love it! You are so right! Most of the best things start off with a crazy or stupid idea…then following through with it by saying that stupid thing out loud! You can’t back out then!

  • I think doing something “stupid” is your internal guidance trying to steer you in a direction that’s brilliant for you. My something stupid was starting a restaurant with no formal training and investing all my money in it. That something stupid was so clearly my calling. And even though I felt I lost my mind if I thought about it logically, I can still recall, prepping something before the dinner shift and knowing in my body that I was exactly where I should be. It was a full body deja vu.

    • Leah Kalamakis Leah

      Yes Silvia, I agree- intuition plays a big part in it. When you know it, you know it and will be able to make it work! Loved your story, I didn’t know that about how you started! I definitely love hearing stories of people that do things without a formal education around it because the truth is it’s not 100% necessary anymore.

  • Stupid, in this case, sounds more like “different”. I think we owe S O much to the people who dare to do “different” things.. They are the trailblazers for so many others. Freedom to be different is HUGE.
    Thank you for an inspiring post (and I’m impressed with the number of people you had leaving their thoughts in the blog post – wow) and wanting to empower us ALL to do great things.

    • Leah Kalamakis Leah

      Yes- different, unconventional… there are many words but I loved how Richie used the term stupid is that’s often how many people feel about an idea when it first pops up. Thanks for stopping by and commenting, I’m super grateful to all the people who shared!

  • I think the highest compliment I can give you Leah is that I wish I would have thought of this blog idea and written it! I can relate to so many of the stories of walking away from a sure thing, taking a giant leap of faith, trusting my gut and… discovering more about myself and success than I ever dreamed of! Keep on being brilliant!

    • Leah Kalamakis Leah

      Thank you Lana- I think it is a topic that should be covered again and again. I’m sure your readers would love to hear your stories and share with you their own!

  • I turned down a job starting up a new school in the summer of this year. It was the hardest decision I have ever made. Though I loved the children, my heart longed for freedom. Freedom from the constraints of the British education system and working a 7am-11pm day. So I quit, with the steely resolve that I needed to work for myself. Only, I didn’t have an idea. So, i’m landed a job in a start-up company and worked on my own project on the side.

    It’s ok, for now…. But importantly, I feel it is a huge leap forward towards my ultimate goal of being my own boss. A destination that has never called louder.

    • Leah Kalamakis Leah

      I know how you feel Ally. The best part about going out on your own is that you can design your business the best way that suits your talents and what you love to do. So find a way to be your own boss & be surrounded by lovely little ones! Congrats on your first leap and I’m sure you’ll get to your ultimate goal soon!

  • Great stories! Very inspiring. I think the stupidest, but one of the best in hindsight, things I’ve done was to turn down a sought after position with a very high end international design company to run my own business. At the time I felt like an idiot for putting my freedom above the opportunity presented, but running my own business instead has opened up so many bigger and better doors, I couldn’t be happier!!

    • Leah Kalamakis Leah

      Love it Shana! Thanks for sharing!

  • What an epic post! Love it!
    Such wonderful and inspiring stories!
    Also, thanks for sharing your thoughts and insights about the book. I didn’t know about it and now I’m definitely going to put it in my book’s wishlist (:

  • They don’t sound stupid, just inspired to take a leap of faith. 🙂 Great post, Leah!… Mandy xo

  • Very inspiring post 🙂 What looks like ‘stupid’ in fact is life altering and awesome sometimes.

  • Great post, thanks.

    Glad we are surrounded by stupidity, it has made being a business owner a more exciting place!

  • LOVE IT! Remember, conventional = boorrrring 😉

  • Love this post! As someone who quit a ‘stable’ position as an Account Director at a top-end agency to live life on my terms, I can appreciate this! It’s definitely not easy. There are tons of bumps in the road and occasionally you might wonder if you should quit but it helps to see other successful entrepreneurs doing it. It’s worth the ride to know you did it your way…as ‘stupid’ as it may seem to others 😉

    Thanks for the insight Leah!

  • This is awesome! After reading your post celebrating your one-year anniversary, I decided to go back and read your blog from the beginning. It’s amazing to see where you started (with this post) and where you ended up just one year later! 🙂

    Thanks for sharing these great tips! It’s inspired me to write a post about this for my Blogtober challenge.

    You rock 🙂

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