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If you want to be an entrepreneur but are struggling to build your asset, try freelancing first.

On this day 1 year ago I went part time at my job and started working on my own businesses. By part time, I mean 6-20 hours a week with 1 to 3 part-time jobs here in Japan, making me close to what I was making for double to work (not quite 80/20 but closer than before). What an exciting time it has been for me. I felt like there was nothing I couldn’t do, and now after a year of it I’m even more emboldened.

I was right to leave my job. Having to be there all day was crushing my motivation to do other more interesting work. Despite this, there is a lot more to being an entrepreneur and building an asset than motivational and inspirational authors like Ramit Sethi, Gary Veynerchuk and Tim Ferriss will prepare you for, even if some of them constantly tell you about how much hard work you need to put in to get there.

I started off trying to build my website Live Work Play Japan into a kind of passive income generating asset with the help of my co-founder Martin. I wrote articles, learned about Google Analytics, Facebook advertising and marketing and content SEO (A lot from Brian Dean of Backlinko), spending as much time outside of my part time jobs as I could to get it off the ground.

I also did all of the logos, featured images, technical and design work on the site as well.

After six months, I started to lose motivation. I had spent more than $300 on servers, website development and themes, Facebook ads and countless hours building recognition and trying to help people in the community of about 1100 Facebook fans and 400 email subscribers. Almost none of them bought the products we are affiliating (more on that another time) and even though our emails sometimes have open rates upwards of 50%, we are still struggling to monetise the site.

Here is the problem

Working on something for a long time without much reward is painful. It is a psychological struggle. When you try to start your own business and after a year you have made a loss of more than $400 you feel like giving up, calling it quits. After all, if you have nothing to show for it, why keep going? As Chris Guillebeau writes in his book Born for This:

“Winners quit all the time.”

However, I think winners quit when they know there is nothing else to gain, but it is important to make the distinction and realise that sometimes you are giving up on something before it has had its chance. Realise not only what you have gotten financially out of your work, but also what you have gained as a professional.

Turn your work into an asset, whether it is making you money or not!

From putting my work out there with Live Work Play Japan I have built up my freelance career, which is helping support my sub-10 hours a week working for the man, and most of my time now goes into my own development and businesses. No longer am I trading my time for money, but now I am trading my time for money AND skills I’ll use for my career and future earnings potential. I have clients paying me to build websites (now my main source of income) as well as a great Facebook marketing client who I enjoy working with. None of this would have been possible without my work on Live Work Play Japan.

Learning everything I have been learning in the past year has made me more optimistic than ever about the future of my career. I’m not bound by a 40-50 hour per week job anymore, so I have time to learn real skills that are going to help me do interesting work in the future. Check here at the bottom of this post for some of the learning resources and people I’ve been following to help me on my journey from full-time worker to full-time entrepreneur/freelancer.

Learning more really is worth spending the time on, and really there is no better way than learning for yourself. Other entrepreneurs I know have spent lots of money learning from gurus and self-confessed experts who charge huge amounts for their online courses. While there is nothing wrong with that and I’m sure there is a lot of value in those courses, I would say that most smart people would be better off learning by spending time and money on their own experiments than paying directly for some kind of course. Learning how you work best and what environments you thrive in is more impoortant than listening to well-intentioned but ultimately demoralising advice from people who might have different goals.

As an example, when I made an information product for English teachers here in Japan, I experimented by dropping £20 into Facebook ads to see how it would do. I’ve since done so many experiments with Facebook advertising that I’m now getting paid to write about using the Facebook Pixel to drive sales (which has just about paid for all of the experiments I’ve done and given me a skill that I can use for the future). I learned a little by reading around and hearing what others had to say, but actually I learned the most from dropping some pocket money into ads so I could see for myself what would work and what wouldn’t. Much less paralysing than wondering if it would work, just try it and see!

The CV/resume of the future

From the kind of work I’ve been doing I’m starting to see a pattern. I think that in the near future our CV will not just be a list of places we have worked and qualifications we have had. It will be the projects you have been most proud to work on, the other talented people you have worked with (and on what), and a grid of connection to who can vouch for your ability to work with others. The skills are a given. Of course you have to be able to do the job, but while necessary that is only a tiny slice of the pie.

Don’t give up on being an Entrepreneur, but try freelancing and working with other people to see what it might take to really start your own business. There is a reason so many businesses fail, and figuring them out before your own business fails is much easier to do as a freelancer helping other companies reach their goals. I would argue that you shouldn’t quit your job to start your entrepreneurial journey. You would be better off starting your company and using your part-time and/or freelance income to keep it going.


Resources I’ve used in the last year to help me on my journey as an entrepreneur and freelancer.

Seth Godin’s Udemy Course – Seth Godin is my hero. I eagerly await his daily blog posts and read every single one of them. His understanding and principles about what work, education and business should and could be are inspiring, and I have shared many of his ideas but never had the perfect words or the platform to say them on. Go subscribe to his blog right now.

Chris Guillebeau – “Art of Non-Conformity” and “Born for This” – really useful books, both of them. The Art of Non-Conformity helped my girlfriend to realise that she needed to change her job, and she quit working as a Assistant Store Manager at Uniqlo and moved in with me in Tokyo. Made a big difference to both of our lives.

Ramit Sethi – I Will Teach You to be Rich. Sounds scammy I know, but he has a lot of insights and his courses are too expensive for me right now anyway. His email list is generally useful and some of his ideas about business can be applied immediately to yours to realise which clients are wasting your time or how to stop thinking like an employee.

Tim Ferris : The 4-Hour Work Week – Life changing book for me and millions of other people. Read past the headline, this book is not about only working 4 hours per week. This book is about building an asset and setting up a lifestyle that you can build around what you want and need. Must read for any entrepreneur out there, even if you think Tim is a bit of a sellout, he has a lot of good points here.

Simon Sinek : Start with Why – A great book, though you can get 90% of it from watching any of his recent talks about Leadership. This will make you understand why your job sucks, not just that it sucks. Leaders make the work environment, if your workplace has crappy leaders, you will be more likely have an unhappy job.

Brian Dean from Backlinko – Good stuff on SEO, has helped my Live Work Play Japan site get to number #1 rank for a whole host of keywords now. Unfortunate as it may seem, SEO is one of the key parts of the question of our generation – “How do I get more traffic?” Haha, what a world we live in.

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