Build the confidence to go out on your own

Reasons why I chose this image: 1) It's a cold winter in Melbourne, and this looks warm. 2) Her kayak looks like a football and 3) she's confident and on her own.

Reasons why I chose this image: 1) It's a cold winter in Melbourne, and this looks warm. 2) Her kayak looks like a football and 3) she's confident and on her own.

I remember when the most exciting part of having to get out of bed and go to work was the thought that I could smash through my work fast enough, so I could then secretly work on my business idea whilst my boss wasn’t looking.

I’m not bullshitting you — I have the notes I used to make into a Word Doc (it was 2003) on my screen as I type this post and they really suck.

But they meant something to me back then.

They were the promise that I could create something from nothing. They were the proof that I could put everything I had learned into practice, not for someone else, but for myself.

I’m sure most Designers have been in this situation — toiling away in someone else’s business and wondering what it would be like if we toiled for ourselves instead.

Such poor creative souls aren’t we?

Before you read on to the end of this post — here is the answer right up front. 

Start now. Whatever you’re doing, wherever you think you’re going, pick up a pen and commit your thoughts to paper. Just start your business idea now.

It will never be perfect. It probably won’t turn out in the exact way that you have planned, just stop thinking about it and start doing something, anything about it.

OK. Now that you know the answer, here’s the important stuff.

The title of this post assumes you need confidence to go out on your own—I agree, you do need an element of confidence, it’s critical to feel empowered and confident when making big decisions such as working for yourself.

You also need a few other things as well.

Whilst I was toiling away planning my own thoughts about the business that I hoped to one day start, I learned a thing or two about a thing or two.
And this was the entire point of simply starting.

Starting (anything) is like creating a compass to help you navigate your journey. The act of putting your thoughts down onto paper (or whatever) is a deliberate exercise in teaching yourself and feeling your way through the idea that you have. 

It will force you to discover new things about the idea you have and in turn force you to go out into the world to learn about these new things you just discovered.

I would do this during work hours (yes, this is true). I would write my notes into a document every day. I had developed business plans, brand strategies, competitive analysis and everything else that you could imagine you’d need to put a decent business case forward. I even had a list of people whom I would recruit at various stages of scaling the business.

I had a firm picture in my mind of what this new business would look like, but lacked a few key things.

Mentors vs Advisors

Early in the year I wrote about the importance of mentors. Go read the post if you haven’t already — it’s not that bad ;-)

I recently read something that spoke about the difference between a mentor and an advisor which really resonated with me.

A mentor is someone whom you meet with regularly, they provide you with advice and guidance on a personal level. They know you, they know your circumstance and they understand the field you’re playing in.

An advisor is a specialist in a very specific area. Law, finance, business development — whichever area you’re weak in, get an advisor. Unlike the regular contact you have with mentors who provide you with very personal guidance, the advisor gives you domain-specific expertise when you need it. 

Surround yourself with people who are either already doing what you’re planning on doing or are on the journey to doing — or possibly have already done it. Make them a part of your world, learn from them and absorb what they know for the sole reason to enable you to make up your own mind about what, and how you will go about heading off on your own.

I had neither of these. In hind sight if I did, they would’ve shown me that I lacked a number of things before I was able to truly go out on my own.

Make meaning

If you’re entertaining the idea of starting something—anything—I recommend you read Guy Kawasaki’s The Art of the Start. 

I read this years ago, and pulled it off my shelf to fill this post with the structure it needed.

Guy’s first piece of advice states:

“The best reason to start a business is to “make meaning” - making the world a better place - by doing something along these lines:
- Increase the quality of life.
- Right a wrong.
- Prevent the end of something good.”

I agree. Business can be a force for good but so many businesses are in it for the money and other stuff.

If you’re thinking of going out on your own to ‘do design’ or ‘do strategy’ for clients. 

Stop for a second and ask yourself ‘Why’?

In The Art of the Start, Guy Kawasaki says to ‘Make a Mantra, not a mission statement’. Something to inspire you and answer the question ‘why do you do what you do?’.

One of my own advisors recently said to me, to find your purpose you need to ask yourself this question (why do you do what you do?) continually until you get to the answer that is as close as possible to ‘save the world’, then you back up one step.


In late 2014, my business partners and I sat down and drew up plans to restructure Tank. Amongst the reshaping and repositioning of our business (another story) we arrived at asking ourselves the question, why do we do what we do?

After a very simple, honest and brief conversation, we wrote our purpose. The simple act of writing it down allowed us to harness the idea within ‘do meaningful work’.

It was the first step, but the most important step in a three year journey of improving what will be a 20 year-old business in 2017.

Write your purpose down.

Prove the concept, create a prototype and ship a beta

How many times have you sat down and had the next great idea only to find that it actually didn’t work? 

Prove the concept.

In some way, whatever you’re thinking of doing make a small version of it, roll out a single project, whatever it takes to prove that your concept works.

If you’re thinking of going out on your own into a freelance business scenario, a single project with a single client for a fee should be enough to prove that your idea is:

  1. valuable to the market
  2. profitable for you
  3. can scale efficiently enough to provide you with some type of income

And if someone tells you that ‘someone has already done that’ when you talk to them about your business idea — feel comfortable in that they’ve just proven to you that there is a market out there for what you’re thinking of doing.

Build the confidence

Ultimately, this article started with the word ‘confidence’ and it should aptly end with it as well.

If you’re lacking the confidence to take a step out on your own, you’re simply fearful of the unknown.

When I first met with Richard and Michelle (my current business partners at Tank) ten years ago, it was for a job interview. An interview as an employee of Tank. By the end of the third interview, I not only gained a job, I also gained two business partners who are still with me 10 years later.

At the time, I also feared the unknown:

  • We just had our first child, could I sustain a family running my own business?
  • If I was to go into business with strangers … my mum always told me to avoid them so …
  • How could I go from a predominantly digital and strategy-focussed career to one that, well, I didn’t really know what type of career

But I also realised a few truths that in themselves, filled me with confidence:

  • I was in my early 30s and prepared to take a risk figuring that if it didn’t pan out, I had a fair bit of time to make things right
  • The strangers who were interviewing me, seemed like nice people
  • Working for myself meant that I could make my own decisions

Balancing these truths gave me the confidence to respond to the offer of employment by posing a question instead.

“What if we were partners?”

I gave it a shot.

I put those five words out there and ten years later I count Richard and Michelle two of my closest allies.

We’ve been through highs and lows and we’ve helped one another through both business and personal crises. In a year the business turns 20 and I’m grateful to have had a hand in shaping it over the last 10 years of its life — we’ve already started planning our 20th birthday party.

So, confidence sometimes takes courage.

And courage at times can seem both a little foolish and arrogant depending on your perspective.

Sometimes you just have to put it out there and see what happens.

And the rest

There’s a wealth of information I could’ve put into this post. Here’s a list of the things I didn’t mention that will go along way towards building the confidence to go out on your own:

  • Read about business
  • Learn about sales
  • Decide if you’re going to work on the business, or in the business
  • If you’re working in the business, continually sharpen your skills
  • If you’re working on the business, continually sharpen those skills
  • Hire people carefully and only when people align with your own values
  • Manage them out if they don’t
  • Be prepared to make the hard decisions and wear the consequences, good or bad
  • Always ask yourself, ‘what does the business need to succeed?’ instead of asking yourself ‘what do I need to succeed?’. There’s a difference.

I'll be writing on most of these points in future posts, but for now ... enjoy.