How Embracing Risk Doubled My Income 5 Times Within 10 Years

Learning what drives value within a business will set you apart.

Casey Winans
Nov 26, 2020 · 11 min read
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Photo by Daniel Xavier from Pexels

started my career as a software engineer. That wasn’t the title used back then, but it represents what I did and how I approached my work. I shined in that role and loved the creativity it offered me.

I was content to sling code all day long — working away in my little world. People that interrupted me were dumb. That went double for marketing people and project managers.

Knowing what was important came naturally to me. At least my definition of what important meant. Yet no one outside my team shared that definition. I saw all sorts of technical issues to fix that should have had priority over marketing projects and customer requests.

In reality, my concerns did not match those who made the big decisions. It took me years to discover why my concerns were never given the priority I felt they deserved. But when I did, my needs began getting traction and my income grew faster than I had ever dared dream.

Discovery #1 — Speak The Language of Business

Early in my career, my ideas were often ignored. I spoke of my needs, but my words fell flat most of the time.

While I have many stories, one comes to mind. I had discovered software that would save me time. A lot of time. When I asked to buy the software, my manager wasn’t convinced. Yet I saw the business spending tens of thousands every year to attend tradeshows where the only goal seemed to be who could get the drunkest.

What I failed to understand was the formula they had perfected over several years. They met with potential customers to build relationships and nurture sales opportunities. After every event, they closed enough sales to more than offset the cost of attending those tradeshows.

They understood the language of business. The tradeshows grew revenue so the cost of attendance was worth it.

But, my request hadn’t shown why it was important to anyone other than me alone. My boss needed to know how the software would make the company more money or save it money.

It was so obvious yet I had completely missed it. The software would allow me to be more productive. If I could do more in the same amount of time, I would be saving the company money.

Once I learned how to describe my needs as a way to cut costs or increase revenue, leadership suddenly took me seriously.

I used this lesson to help land my next job.

Takeaway #1

Understanding how you can grow your company’s revenue or reduce its costs is key to unlocking your career potential. Once you’ve mastered framing your ideas in that manner, your leaders will be eager to learn more.

Don’t be shy here. Do your homework and know the benefits. If you find it hard to make a case for growing revenue or cutting costs, take a step back and rethink what you want to accomplish. There is almost always a path towards a benefit. But if not, you know to move on.

Side Note: Great businesses don’t just look at growing revenue or cutting costs. There are a number of other advantages that require long-term vision and an appetite for innovation. Those concepts are beyond the scope of this article.

Discovery #2 — Go Where The Opportunity Is

The city I grew up near had seen better days. Few job prospects and frequent stories of yet another company leaving the area filled the airwaves. It was a beautiful area, but couldn’t seem to shake the stigma of being part of the “rust belt”. The only visible business growth involved low-paying jobs within retail and food services.

I was in my late 20s, with a wife, two daughters, and another child on the way. The major employers were underwhelming and I was already making top pay for the area. If I wanted to increase my income, I needed to explore moving to another city or even another state.

My wife and I agreed it was time to move. The idea of leaving our families weighed heavy, but it would benefit us and our children in the long run. Plus, coming back to visit wasn’t a big deal.

I interviewed for jobs in many regions, but one stood out. We knew people there already, the cost of living was comparable, and it had a reputation for being innovative and fast-growing. Plus, the weather was amazing. While we had grown up with long winters and short (yet beautiful) summers, this was the opposite and much closer to the ocean. My wife loved the ocean so it was a no-brainer.

Two companies had extended attractive offers. While one felt like an easy transition, it offered few opportunities to advance. But the other one felt like a massive risk. It built proprietary software for a niche industry and I worried my career growth would suffer.

In the end, I accepted the software job in the niche industry. They had offered me double the salary I was able to land up north. It was a great fit, even if it was scary.

This job paved the way for a surprising career.

Takeaway #2

Don’t be afraid to make bold decisions like moving to where opportunities are abundant. This doesn’t mean you can’t move back to where you grew up later on when your needs change or new opportunities arise.

When considering a move, I recommend looking at the quality of life in that region as well. Don’t just chase money or one specific opportunity, if you’ll only need to move yet again in a couple of years. Unless that is something you enjoy, and if so, don’t let me slow you down.

Discover #3 — Specialize To Add Exceptional Value

I worried my skills would not be transferrable given the software company’s proprietary framework. What I failed to understand was I had been in its industry for my entire career. Calling it by something else or focusing on the generic aspects of my work had clouded my vision.

It was then that I realized what was most important. The ability to bring critical thinking to the table. The ability to see complex problems and break them down into manageable pieces. The ability to work with many programming languages and selecting the right one for the task at hand. Those were my transferrable skills. Every other aspect of my job and prior jobs had been background noise.

Upon starting my first major project, the concepts that I believed would be foreign were not. I had seen those concepts many times before yet had failed to recognize their importance. This allowed me to shine early on and focus on the truly difficult challenges.

Promotions came easy once I understood where my efforts added the most customer value. I became the guy to call when things were not adding up within the complex core of the software. And then I became the person leading massive projects and mentoring junior consultants.

Before long, I stumbled upon a new product that served an even narrower audience. A niche within a niche, go figure. The problems were rampant and I shot my mouth off on social media to express my frustrations.

Warning: I don’t recommend shouting negativity over social media. I got extremely lucky not to lose my job and severely stunt my career ambitions.

As counterintuitive as it may seem, that rant led to a big promotion managing a team of consultants, analysts, and engineers. The mandate of the team was to position the niche product for success and set realistic expectations with my colleagues and customers at the outset. Effectively, heading off failure before a project could go off the rails.

Managing people was something I had never truly considered until just a few months prior to my rant. Managers had been an obstacle to me more than anything else. At least that was my backward view of them up to that point. But now I see things differently.

By this time, I realized my potential and felt held back by what the software company would allow me to do. So I talked to a recruiter for guidance on what my next steps could be. She lit a fire under my butt to continue pushing forward with management and to better understand customers' needs.

This led to taking a position with a Canadian company to learn how a customer of the software company operated. I had seen pieces while working on their projects but hadn’t seen how they used the software long-term or interacted with their customers. This would allow me to round out my skill set with both an understanding from the vendor’s perspective as well as from a customer’s vantage point.

This company also paid very well, allowing me to significantly increase my income yet again. They valued my expertise and understood I would save them money by shrinking project timelines and improving outcomes.

This next job opened my eyes to what would come next.

Takeaway #3

When you can no longer improve your skillset where you are, look for your next opportunity. We no longer live in a society where you work for one employer for your entire career.

If you’re unhappy in your current position and can’t find a way forward, your departure will make room for some other person who is a step behind you in their similar journey.

Never stay where you can’t thrive. Take ownership over your career and seek out the next challenge. Complacency will severely limit your career potential.

Discovery #4 — Sell Your Specialized Knowledge

The Canadian company showed me what customers really needed to be successful, which expanded my perspective. These were important lessons that had alluded me while working for the software vendor.

I no longer had to defend defects or design decisions within the software. I could be candid when reviewing features and use cases. This allowed me to create more practical solutions.

The clients of my employer asked my team to help them with external projects. With this, we were able to add a new revenue stream for our department, making us all more valuable to the company.

As a side effect, I grew to love consulting. Even though I had always thought my prior role at the software vendor was consulting. I was wrong — way off base — given I had never been able to be neutral before. In the past, when customers had discovered something they did not like in the software, I had regularly played the role of a punching bag. Things were now so much better.

The clients valued what I brought to the table. This also allowed me to be transparent about where the software worked well and where gaps existed. Helping the client address needs with people and procedures (as opposed to building overly complex technical solutions) greatly expanded my skill set.

The fees clients were willing to pay for access to my team and I had me rethinking working for someone else. I was capable of finding clients, negotiating deals, and delivering value. Why not take the next step and hang my own shingle?

That’s just what I did. I found two partners and we set sail on our first entrepreneurial journey together.

Takeaway #4

Look for ways to market and sell your own expertise. The experience and expertise you’ve spent your career building have real value. The challenge is understanding how potential customers view that knowledge.

Once you’ve removed the middlemen — former employers — you are completely free to price your services as creatively as you can. While most people start out billing by the hour, look at what the customer truly values and experiment with charging for the outcome you help create. Don’t settle for income based on your effort alone. While it’s less risky (for you), it’s also less rewarding when you deliver something hugely important for your client.

Discovery #5 — Sell Other Peoples’ Knowledge

My business started with three founders and one contractor. We worked our tails off, billing as many hours as we could until that became unsustainable. That’s when we started building our team. We made money by charging clients an hourly rate for improving their businesses so more people meant more money.

While I’m not a fan of hourly billing, at that time it was the only pricing solution I understood. Even with all its drawbacks, we made great money. What had started out as selling my knowledge transformed into selling my employees’ knowledge. This was much more scalable and, over time, allowed me to focus less on my own contributions. Instead, I focused on ensuring we had a steady pipeline of work coming in.

Within three years, we had a team of several dozen employees and contractors. The risk was rewarding. Although we had many families counting on us to provide steady income, our growth made the risk attractive enough to keep growing.

It was by this time that I had doubled my income yet again and could see how it was possible to do it again and again.

But my ideas for the future direction of the company did not line up with my two partners so I sold the business to them and pursued my next adventure.

Takeaway #5

Look for ways to grow beyond your own contributions. Become a dealmaker — connecting others with opportunities. There is value in the margin and you will find new ways where you can add value.

This means you need to think beyond what you can do personally. Asking yourself questions about what and who you know can open doors that chasing your own work would never expose.

You will be taking on risk at times, but when done well, everyone involved should benefit.

Discovery #6 — Build Equity Using Knowledge

Once I had decided to sell the business, it unlocked my equity. As the business had grown, its value had increased, which increased the value of my share of the business over time.

The business had been worth nothing when we started it. We were the business. If we stopped, the business would no longer exist. Yet as we grew, the business took on a life of its own. It generated revenue even when we were away on vacation or sleeping in our beds.

This is the power of building equity in a business that can operate without your explicit involvement.

The risks were real and sometimes overwhelming, but the reward for helping customers and attracting a great team was worth it.

The sale of my first business increased my income even further. And unlocked new ways to continue building wealth.

Takeaway #6

You can build real value by creating systems and teams that leverage your expertise and experience. While the risk of employing people is very real, when done well, the value of your business will outpace any contribution you could make by yourself.

Over time, you can even step away from the business once your team and systems are in place. This is how many very wealthy people scale their income. There is no limit to how many times you can do this beyond how you choose to spend your time.

Final Thoughts

The lessons I learned with my first business and the new ones from growing my current businesses will pay dividends for the rest of my career.

Nothing I’ve learned can’t be repeated by anyone else. I’m nothing special. In fact, you can be much more successful. I learned most of this through trial and error, making many mistakes along the way. You have the benefit of being able to avoid the same mistakes by standing on my shoulders and those that make my success look like table scraps.

Hey! If you found my post entertaining or insightful or offensive, consider signing up for my newsletter, The Service Zealot, where I get much more opinionated.

The Ascent

A community of storytellers documenting the journey to happiness and fulfillment.

Casey Winans

Written by

Business Strategy & Experience Advisor. Sold my last service business after growing it to $10MM in annual revenue. More at

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join thousands of others making the climb on Medium.

Casey Winans

Written by

Business Strategy & Experience Advisor. Sold my last service business after growing it to $10MM in annual revenue. More at

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join thousands of others making the climb on Medium.

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