Berlin & Los Angeles



It’s been almost 2 years since I bade farewell to the corporate world to live the life of my dreams: being location independent, working on projects that inspire me.

How time flies. It’s been quite a journey, and I don’t expect it to get any less exciting or challenging anytime soon. If it did, well, it wouldn’t be much fun then!

Over the course of the last 22 months, I’ve experienced a series of firsts:

  • Secured a year’s seed funding from a client for my then week-old startup
  • Wrote 500 Google Glass app ideas for said startup within 6 months
  • Gave a short speech about said startup at a Google Developer Group networking event at the Google office in Berlin
  • Secured regular paying clients for my freelance copywriting services
  • Formed a collaboration with a Berlin-based freelancer’s cooperative, whereby I’m now part of their Creative Bureau

I’ve also experienced my share of setbacks, as with anyone else treading the uncertain waters of entrepreneurship. If I had to pick the 8 most valuable lessons I’ve learnt since taking the leap, it would be the following:


1. You don’t need to have it all figured out

Having a plan is great, but it means nothing without action.

A great business plan doesn’t guarantee success. Only putting it out there and getting real feedback from customers will tell you if you’re on the right track. And the sooner you know, the sooner you can adapt and change.

So while having a plan is useful, it boils down to having clarity of what you want to achieve and trusting your instincts. The rest will follow.

Plans will change. No one can predict the future.


2. You DO need to have the stomach for it

Life as an entrepreneur (or even a freelancer) is uncertain, often scary, but totally worth it. Persistence is a prerequisite.

I’ve found myself wondering numerous times (and still do occasionally), whether I have totally lost my mind. It requires discipline, commitment and faith in yourself, a hundred times more so compared to working for someone else, because this is YOUR business.

Whether you succeed or fail is ultimately up to you.

It’s a challenge, but a very worthy one, because the rewards are invaluable. It’s mind-blowing, the kind of opportunities you find when you open yourself to them.

“Only those who will risk going too far can possibly find out how far one can go.” – T. S. Eliot


3. Surrounding yourself with like-minded people is key

Having a support group is essential. You need people who get what you’re trying to achieve, who will understand, inspire, motivate and also give you the necessary kick-up-the-butt when you get stuck.

I have been incredibly fortunate in this respect. Not only do I have an online support group via The Hundred Dollar Club, I have also met inspiring entrepreneurs and like-minded individuals along the way, often in the most unlikely places.

They keep me energised and motivated, inspiring me to keep going despite my doubts.


4. Be open to advice, but listen to your gut instinct

I believe in being open to different views and ideas. You can always learn something from the next person, but only apply what feels right to you.

In my world, I define success based on the ‘New Rich’ philosophy that people like Tim Ferriss and Chris Guillebeau live by.

“The New Rich (NR) are those who abandon the deferred-life plan and create luxury lifestyles in the present using the currency of the New Rich: time and mobility.” – Tim Ferris (The 4-Hour Workweek)

One way I discern advice is to ask myself: does the advice fit in with my definition of success? Is there a way it can fit? If the answer to both is ‘no’, I disregard it and move on.


5. You don’t have to do it the way everyone else is doing it

My mantra in everything I do is: Does it make sense? If not, why am I doing it?

Oscar Wilde said this: “Everything popular is wrong.”

While it might seem extreme, I agree with the notion that we have been conditioned to follow the masses almost on auto-pilot, which has progressively diminished our ability to analyse a situation objectively and to make independent choices.

I admit to being rather selective about the type of projects and clients I work with, despite the fact that I could do with the money. But if all I wanted was to make money, I wouldn’t have left the corporate world. I left because I wanted my work to have meaning. Not just to do as I’m told.

The ‘why’ behind the project, organisation or brand is as important to me as my ability to deliver the skills required. I realise it’s not always a practical choice, but it’s what I’m compelled to do.

Just because it’s not the conventional way doesn’t make it wrong.

Does it make sense (for you)? If not, why are you doing it?


6. Comparing yourself with others holds you back

The problem with comparing ourselves with others is that we often feel inferior and woefully inadequate as a result. It usually makes us feel that we’re not good enough. I’ve been guilty of that for most of my adult life.

I find that a more accurate measure of progress is to compare where we are today with where we were yesterday, last week, last month, or a year ago.

In short, the only person you should be comparing yourself with is: yourself.

And instead of focusing on how much further you have to go (which can be demotivating), focus instead on how far you’ve come. Give yourself a pat on the back for all you’ve accomplished, and enjoy the ride!

I’m pretty sure Seth Godin didn’t become a best-selling author overnight.


7. Give yourself permission to fail

I wrote to Derek Sivers when I first quit my job and told him about my transition into entrepreneurship. He was very cool, and was kind enough to share this valuable piece of advice with me:

“Much of success is luck. What the public loves will usually be a surprise. So do many things, giving each one 100%, but if the public just isn’t excited about it, walk away and do something completely different. Knowing this in advance, your first step should be to just do anything useful to others, realising it’s just the first of your many endeavours and shouldn’t be taken too seriously.”

A few months back I was faced with a difficult decision regarding my startup. I’d invested a whole year of my time and energy into it. But it had come to the point where I had to be honest with myself. The reality of it was, I wasn’t any closer to achieving my goals after a whole year of working on it. It was a tough decision, but it had to be made. I decided to call it quits on the venture.

Far more important to fail and learn from it, than to get stuck in a rut.


8. If you don’t ask, you won’t get

No one likes rejection. But if you don’t ask, guess what? You’ll have exactly 0% chance of getting what you want. By asking, you increase your chances by 50%. Simple math, really.

I was desperate for work a few months back, when I decided to leave my startup to focus on my freelance copywriting. I was in the process of negotiating a monthly contract to provide my writing services to a local tech organisation. Unfortunately the contract fell through, due to internal organisational issues.

I figured I would be frank with my client. I told him I was strapped for cash and asked if he would recommend me to his contacts. Well, that question led me to securing a four-day writing gig for him. It wasn’t as good a deal as the 3-month contract I was previously negotiating, but it was definitely better than nothing. He’s also one of my regular clients now.

I don’t hesitate to ask these days, though I do so knowing full well the answer could be ‘no’. Sometimes it works, other times it doesn’t.

But if you don’t ask, you’ll definitely not get.

It’s that simple.

Have any you’d like to add to the list? Do share. I’d love to hear them!

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Lindy Siu