How to make scary decisions; If you want to operate outside your comfort zone, get comfortable being uncomfortable

How to make scary decisions

January 28, 2014

Kate Jones

If you want to operate outside your comfort zone, get comfortable being uncomfortable.

Rebecca Butler saw plenty of scary decisions ahead of her when she decided to open her own business.

The former proposals manager had spent years working in the corporate world and the idea of leaving such a comfortable environment seemed risky.

“There’s a lot of tough decisions to make, but the main one was getting the courage to put myself out there,” she says.

Like any entrepreneur, the possibility of failure loomed over every decision Butler made. But the Melbourne businesswoman found a gap in the lucrative children’s market and wasn’t going to leave it open.


“It’s really quite nerve-racking to take your idea, develop it and then put it out there for possible failure,” Butler says.

“There’s a quote I heard, ‘Get comfortable with feeling uncomfortable’ which sounds cheesy, but is very true.”

Butler and her husband put their personal savings plus two years of Butler’s time into – an ecommerce platform for small businesses to sell children’s, baby and maternity products.

The site launched just five weeks ago and so far, despite further daunting decisions still to come, Butler says it’s all been worthwhile.

Anyone who has taken the leap of faith to start their own business has pushed themselves through a series of difficult decisions.

But Mat Jacobson from online business and management education provider Ducere says it’s all a matter of having the right attitude.

“If you are approaching a decision as a scary one, you’re not approaching it with the right mindset,” he says.

“The decision to venture out and build a business shouldn’t be scary, particularly if the alternative is working for a multinational corporation where you have no control and are at the whim of other people’s decisions.”

The mere thought of disaster is enough to turn budding entrepreneurs away from their business dreams.

Jacobson believes this is because failure in the business world is judged more harshly in Australia than other countries.

“People shouldn’t be scared to try, but the issue of not succeeding with a start-up is an unfortunate characteristic of Australian culture,” he says.

“In the US, it’s viewed as a learning experience.”

Having a mentor to help work through the tough calls is a great way to feel less daunted by difficult decisions, he says.

“A mentor acts as a sounding board and can provide good advice because they are impartial and don’t have a vested interest in the business – just a vested interest in you succeeding,” Jacobson says.

Firing an employee ranks high on the list of daunting decisions for business owners.

It usually comes down to a matter of performance or cost, but whatever the reason it’s an incredibly hard call for any business owner to make.

For those employing a small group of staff, it can be a particularly emotional decision and one that may take longer to consider than most business arrangements.

Firing someone was the hardest business decision Dianna Butterworth, who runs women’s cufflink retailer Miss Links, has made.

“I’ve had to move people on from the business and it’s never easy letting people go, especially when times are tough economically,” she says.

“It’s probably the worst thing I’ve had to do in my career.”

Butterworth says she summoned the courage to give a worker their marching orders by reminding herself to put her business first.

But even then it’s a last resort option, she says.

“I always give people all the resources and training they need before deciding their performance isn’t adequate for the role,”

“It’s not easy especially when emotions can come into play, but if you’ve looked at all the other options in trying to get the best out of the person and to get the job done, and there’s still capability issues and cultural issues, then the only thing is to let them go and find someone who can better fill the position.”

The toughest choices can often be the best choices. While these should not be made in haste, it never pays to agonise on a complicated decision.

Jacobson says strong business leaders know how to move fast.

“The worst thing in business is people who cannot make a decision,” he says.

“If you take a long time to make a decision you’re business will be stunted and everything will slow down.

“Realise that you are going to make mistakes but try to move at a rate faster than your competitors and you should be right about 80 per cent of the time.”

About bambooinnovator
Kee Koon Boon (“KB”) is the co-founder and director of HERO Investment Management which provides specialized fund management and investment advisory services to the ARCHEA Asia HERO Innovators Fund (, the only Asian SMID-cap tech-focused fund in the industry. KB is an internationally featured investor rooted in the principles of value investing for over a decade as a fund manager and analyst in the Asian capital markets who started his career at a boutique hedge fund in Singapore where he was with the firm since 2002 and was also part of the core investment committee in significantly outperforming the index in the 10-year-plus-old flagship Asian fund. He was also the portfolio manager for Asia-Pacific equities at Korea’s largest mutual fund company. Prior to setting up the H.E.R.O. Innovators Fund, KB was the Chief Investment Officer & CEO of a Singapore Registered Fund Management Company (RFMC) where he is responsible for listed Asian equity investments. KB had taught accounting at the Singapore Management University (SMU) as a faculty member and also pioneered the 15-week course on Accounting Fraud in Asia as an official module at SMU. KB remains grateful and honored to be invited by Singapore’s financial regulator Monetary Authority of Singapore (MAS) to present to their top management team about implementing a world’s first fact-based forward-looking fraud detection framework to bring about benefits for the capital markets in Singapore and for the public and investment community. KB also served the community in sharing his insights in writing articles about value investing and corporate governance in the media that include Business Times, Straits Times, Jakarta Post, Manual of Ideas, Investopedia, TedXWallStreet. He had also presented in top investment, banking and finance conferences in America, Italy, Sydney, Cape Town, HK, China. He has trained CEOs, entrepreneurs, CFOs, management executives in business strategy & business model innovation in Singapore, HK and China.

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