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5 Skills I Learned in the Military That Helped Me Become a Successful Entrepreneur

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things learned in the military
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The moves I’ve made in my career from the military, to the mining industry, to running a multinational business in Latin America, aren’t linear. It’s not every day an ex-Australian military officer finds their niche in Latin American business.

Graduating from Australia’s Royal Military College and Defense Force Academy, I served as a commissioned officer in the Australian Army for nearly 11 years, completing operational tours to Central Asia and the Middle East.

The transition from various Army engineering and infantry roles through to managing a team of legal and financial executives was neither quick nor painless. But, as I entered the company formation process, I found my military service played a significant role in shaping my entrepreneurial fitness. The skills I developed in the Australian Defense Force supported me through several commercial iterations more than once.

Here are some of the key connections I drew between core military values and those I apply to the boardroom environment:

1. Be calculated and decisive

Unsurprisingly, a crucial requisite of military functionality is working quickly and effectively under pressure. This rings especially true for the strategic planners of operations: the commissioned and non-commissioned officers.

My military role made tough demands on me to decide on the best course of action for myself and my team. When deployed overseas, making the wrong decision or not making a decision fast enough could mean failing our mission, and putting people in danger.

In business, it’s vital to understand, analyze and communicate the risks involved in the options laid out before you at various stages. Making offers to clients, moving into a new market, investing large amounts of money into projects. And decisions need to be made based on this analysis before these opportunities pass by.

I can confidently draw on my experiences in service to act fast and capitalize on opportunities as they become available, and make tough decisions in high-pressure situations.

“You cannot make progress without making decisions.” – Jim Rohn

2. Resilience is key

Resilience is fundamental to success in any military career. In training and on operations, one soldier’s spiralling morale could put an entire section in danger. Military personnel are vetted for their adaptability and mental strength from day one, using tried-and-true techniques to push people to their limits.

Having a high level of resilience allows you to cope when things don’t go to plan in business. Investments might not show returns as quickly as hoped, a competitor snatches up an important client, or a difficult situation arises between staff that needs careful management.

I can confidently draw on military-learned techniques to support my own and others’ resilience in the office. Being able to maintain a high level of morale among teams fosters productivity and a willingness to ‘soldier on’ in challenging situations.

3. Leadership and cooperation

People in leadership positions are those that others turn to for advice and support. As a leader, you have to be prepared to make tough decisions that others can’t or won’t. A high-performing team has a courageous, empowering, and communicative leader at its helm.

This is as true in the military as it is in business. Building the right team and driving them to success is both challenging and rewarding – whether the outcome is securing a key logistical foothold to allow aid and other supplies to travel into a war-torn area, or seeing a newly-opened office secure its first major client.

4. Discipline

Not every soldier has an easy time appreciating the ubiquity of drills in their military workplace, nor their role in underpinning the success of a smooth operation. But a lack of discipline is tantamount to putting oneself and others at risk. Ignoring lawful orders, or not applying proper first-aid to a fellow soldier, are a couple of examples of this.

To me, commercial discipline means being professional always, even in stressful or frustrating situations. Maintain integrity in everything you do, and don’t cut corners. Carrying out proper legal and financial procedures means staying compliant under local law, and avoiding complications with authorities.

Staying committed to an objective and refusing to drop standards enables you to build a credible reputation for your business that clients hold in high regard.

“We don’t have to be smarter than the rest, we have to be more disciplined than the rest.” – Warren Buffett

5. Cultural awareness

Finally, but no less importantly, showing respect for cultural customs in business is essential for cultivating strong professional relationships. Being aware of your cultural background, and sensitive to those of others, will help build social connections, and make you more relatable to others.

Foreign militaries operating in troubled parts of the world understand that building trust with local individuals and communities is imperative. Without that trust, moving around becomes difficult and more dangerous. To gain trust, soldiers must show respect for people’s culture and way of life.

The same is true in business. A small hiccup such as not shaking hands, or giving an air-kiss to a new acquaintance here in Latin America could start an entire working relationship off on the wrong foot. Cultural sensitivity shows a willingness to embrace people and their society. Never underestimate the significance people place on this element when evaluating your suitability as a professional partner.

It’s no secret that commercial success requires passion, hard work, and dedication. Don’t be afraid to call upon your own and others’ previous experiences to find solutions to problems or forge ahead with complex projects. For military personnel considering testing out their business acumen, be confident that your years of service to your country have also set you up for success in the world of business.

Craig Dempsey is a seasoned business professional in Latin America. He is the Managing Director and Co-Founder of the Biz Latin Hub Group that specializes in the provision market entry and back office services in Latin America. Craig holds a degree in Mechanical Engineering, with honors and a Masters Degree in Project Management from the University of New South Wales. Craig is also a military veteran, having served in the Australian military on numerous overseas missions and also a former mining executive with experience in various overseas jurisdictions, including, Canada, Australia, Peru and Colombia.

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Entrepreneurs

The One Brutal Mistake That Keeps Most Entrepreneurs Stuck at Six Figures (And the Fix That Unlocks Seven)

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Image Credit: Joel Brown - Addicted2success

You built something real. Customers are coming in. Revenue is growing. But no matter how hard you grind, it feels like you’re hitting an invisible ceiling. The business owns you more than you own it, and scaling feels like a distant dream instead of the next logical step.

I’ve seen it destroy too many sharp founders. They’re doing everything “right”—working longer hours, chasing every opportunity, saying yes to every client. And yet the growth stalls while their stress skyrockets.

The mistake isn’t effort. It’s identity.

Most entrepreneurs still see themselves as the indispensable hero who has to touch every single part of the business. They built it with their own hands, so they believe only they can run it at the highest level. That belief is exactly what caps them at six figures.

The shift that changes everything is deciding you are now the leader of a system, not the worker inside it.

You stop being the best operator and start becoming the best owner. That means ruthlessly auditing where your time is spent and handing off everything that doesn’t move the needle on growth. Yes, it feels scary. Yes, it feels like you’re losing control. But the entrepreneurs who break through are the ones who trust the process more than their ego.

Here’s what that actually looks like in practice.

First, identify your $10,000-an-hour activities

The ones only you can do that truly grow the company. Everything else gets documented, delegated, or deleted. Most founders I know are shocked when they finally track their time for two weeks straight. They discover they’re spending 60-70% of their week on things that could be handled by someone else at a fraction of the cost. The ego loves to whisper that “no one can do it as well as me.” That voice is expensive. It costs you leverage, it costs you time with your family, and it costs you the mental bandwidth to actually think strategically about the future of the business.

Second, build repeatable systems for the rest.

Not fancy software. Simple checklists, processes, and people who own outcomes. Your team stops waiting for your approval on every little thing. This is where most entrepreneurs get stuck—they hire help but never actually transfer ownership. They create bottlenecks because every decision still funnels back to them. The fix is to document the process once, train someone thoroughly, then step back and let them own it. Yes, there will be mistakes in the beginning. That’s the cost of building something that can eventually run without you. Every mistake becomes a better system.

Third, measure what matters.

Revenue per employee. Customer acquisition cost. Lifetime value. Stop celebrating busywork and start obsessing over leverage. I’ve watched founders go from celebrating “we’re so busy” to celebrating “we added three new team members and revenue per person went up 40%.” That’s the shift. When you start measuring the right things, your decisions change. You stop hiring to offload tasks and start hiring to multiply output.

The hard truth is that most entrepreneurs never make this transition.

They stay the bottleneck in their own business. They become the ceiling. And the business grows to the exact size that one person can manage with heroic effort… then it plateaus. The ones who break through are willing to feel uncomfortable for a season so they can build something that actually scales.

You didn’t start this journey to trade one boss for another… especially when that boss is you. Let go of the need to be the smartest person in every room. Your job now is to build something bigger than yourself. The ceiling isn’t real. It’s just the point where your old identity stops serving you. The question is whether you’re willing to let that old version of you die so a new one can lead.

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