I always wanted to try rally racing. It didn’t always seem like an opportunity I would have, but when I was offered the chance, I jumped at it. I had a lot to learn through training, and the race itself was a thrill of risks and challenges. The whole process taught me a number of lessons about myself as well as about business. But through it all, the sensation I consistently felt was fun. It was everything I hoped it would be and more. I was truly enjoying myself.

And that, as it turns out, was the the fourth – and maybe most important –  lesson I learned about business by rally racing. In the daily routine, we can forget that business is an adventure. Every entrepreneur or innovator who ventured to start a business took a big risk, a leap of faith. They decided to follow a path they felt strongly about. And that adventure can be thrilling, but it can also be terrifying.

If rally race car drivers become so fixated on winning — or on not crashing — it hardly matters whether they win or not, because they won’t be able to enjoy the experience. That’s not to say that you shouldn’t race to win: you absolutely should. But you should also be able to be in the moment and have fun with it.

It’s the same with business. I’ve spoken to many entrepreneurs who become so stressed about keeping their business afloat that they forget to enjoy the journey. They work hard to succeed and the daily grind can drag you down. Every entrepreneur knows and understands that. And it’s is understandable, because there are so many things to worry about when it comes to running a business. Sometimes it’s easier to say, “I’ll enjoy myself when I finally reach my goal.” But going about business — or anything — without enjoying the journey itself is bound to lead to undue misery. Where’s the satisfaction of taking that leap if only to let stress drive you?

And that’s where I realized that all of my observations about the parallels between rally racing and business come together.  Don’t be impulsive, but put aside the overthinking. Always strive for your vision, and have co-drivers that you can trust (but know when to trust your own instincts, too). When you keep all of these lessons in mind, it will be easier to relax and feel good about what you’re doing.

Whether it’s learning to drive a race car, starting a business, leading a transformational effort, or navigating a personal endeavor, it’s always better if you can have some fun along the way. Take calculated risks, send the car sideways once in a while to see how it feels, let yourself recover, and enjoy the ride.

When was the last time you realized that you need to stop and ‘switch on’ the fun? Did you ever have a moment where you needed to tell yourself to not just go through the motions, but be present in the moment and open yourself to the adrenaline-rush that you get from this amazing experience of running your business?

Would love to hear your experiences!

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No rally racer drives alone. There’s always a “co-driver” who rides shotgun in every rally car. And in an actual race this co-pilot, is talking literally constantly. Every step of the way, they give audible cues and provide instructions about the terrain, the degree of every single turn, alerting the driver to any unusual danger, and keep track of the distance of each turn and each straightaway.

When I recently had my first experience with rally racing, I learned quickly how vital it was to my success to have a good co-driver and be able to blindly rely on them. Without the co-driver, rally racing drivers could crash five times over, and certainly wouldn’t cross finish line ahead of the competition.

Interestingly, it’s the same with business. We all have co-drivers, whether in our personal life or in business. Whether they’re investors or business partners or staff, no entrepreneur does it all alone, and we shouldn’t. To succeed in business, we need partners we can trust.

The Key Is Communication

In rally racing, co-drivers use a specifically coded rally language. It uses the minimal amount of words necessary, but provides total accuracy for the driver to hear, process, and take action while propelling the vehicle forward through all the chaos at up to 140mph.  If the driver misunderstands or the co-driver miscommunicates, things can fall apart and the race is over.

Some might argue the co-driver is actually the more important person in the cockpit. But in reality, the two are completely interdependent. One cannot win a race — or even come close — without the other. Their communication must be fluid, constant, and seamless. The driver must at all times be listening intently, processing, and acting on the information from his co-driver.

In business, it’s important to have strong communication between yourself and your “co-drivers.” It’s just as important for you to listen to them as it is for them to advise you. A lack of communication can lead you to overlook obstacles, misjudge situations or lead you to go too fast or too slow. Unconditional and blind trust is what makes the relationship between driver and co-pilot special. In business, if investors don’t trust you, your business is sure to crash and burn. If your partners have no trust in you or into each other, you’ll never be able to move your business in the direction it needs to go.

Of course, in rally racing, each driver has only one co-driver; in business, you’ll have no shortage of people who have advice for you, who want to be your co-driver. With so many voices in your ear, it’s important to be able to tell which ones need to be tuned out and which ones should be heeded. It all comes down to choosing your co-drivers carefully. Ultimately, we are responsible for our own decisions, but our trusted co-drivers can help us avoid disaster, if only we communicate.

Did you experience similar situations with your co-drivers? How has a co-driver helped you and your business?


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Like any entrepreneur, I usually find a way to relate most things back to business, whether intentionally or not. It just happened to me again, when I had the opportunity to take part in a rally race for the first time. One of the main lessons I learned from the rally experience that can be applied to running a business? The need for a focused forward vision.

The Danger of Fear-Based Focus

In rally racing, you’re always looking where you want the car to go next. It’s not about where you are or gauging where you don’t want to go. You need to look through the turn at the exit, not at the tree or ditch where you may find yourself if you don’t execute that turn properly.  For most of us, this approach doesn’t come naturally. When we find ourselves in a potentially threatening situation, our instinct is to look at the danger. We fixate on what can go wrong, because that’s what we need to keep an eye on.

But professional drivers will tell you that if you spend too much time looking at a tree, cone, ditch, or wall, that is exactly where you will wind up. Your brain simply directs your hands to steer the car in the direction of your focus. As advanced steering skills start to automatically take over throttle and brake, your feet will start to steer you that way, too!

As entrepreneurs, we have a habit of stepping into the same mental trap. It’s not intentional. No one would start a business if they didn’t have a vision of where they wanted that business to go. No one would go through all the risk of innovation if they didn’t think their ideas would bear fruit. But in the midst of actually running a business, it’s easy to lose the forest for the trees and focus more on the risk than on the opportunity.

What if you lose your investors? What if someone else has already executed a similar idea? What if they did it better than you can do it? What if there’s not enough interest in what you’re doing? And it’s not just concerns of “what ifs” but present problems as well. Sometimes it seems as though all you can do is keep treading water and save your goals for a later time when you’re in a more comfortable place.

Breaking the Habit and Focusing on Vision

If you spend too much time focusing on what’s directly in front of you, you’ll likely avoid every possible pitfall. But it’s not a great way to successfully grow your business. At best, your business will start to stagnate. At worst, you’ll drive yourself straight into one of the very dangers you wanted to avoid in the first place. So how do you break the cycle?

Simply apply the same strategy race drivers break the cycle of worrying about every tree or ditch or sharp turn.

Race drivers break the instinct of focusing on the danger by training themselves to look where they want to go. They start with the end in mind. They look through the turn to the exit, as opposed to the entry point or middle of the turn. This has a subconscious effect on the body. It allows them to control the car in a way that sets it up to enter, progress through, and exit the turn for maximum speed, efficiency, and safety.

As innovators and entrepreneurs, we all have our own professional versions of loose gravel, snow, ice, or wet tarmac under our fast-moving transformation efforts. Having a healthy awareness of the consequences of mistakes along the way is great. But fixate too much on these obstacles and they’ll end your ride. Look through the turns. Trust your ability to navigate a smooth and successful progression through a challenge or important milestone.

I’m curious to hear from you if you have experienced this fixation on the problem? How did you channel your inner rally driver – and how did you overcome this challenge?

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Recently, I had an opportunity to participate in a 3-day rally race driving school with the amazing pros at DirtFish Rally School in Snoqualmie, WA. I don’t consider myself a racing nut butI very much enjoy driving, whether it be a jeep on a 4×4 trail, a BMW unlimited on the autobahn, splashing “beast mode” through rain puddles with my 5yr old, or mud bogging in Hungry Valley with friends. On occasion, I get in the car, turn to the back seat and ask my kids, “Who wants to go fast?” …no doubt a question that I’m really just asking myself, knowing in advance what the answer is.

If you know anything about rally cars whether as a driver, passenger, or YouTube spectator, you can imagine how someone with my penchant for speed and dirt would be attracted to a driving school like DirtFish.It was everything I expected and more. Three days of classroom instruction, then driving, ripping the e-brake for extreme turns, throttle-steering, and the added bonus of a mix of sun, rain and snow resulted in quintessential rally experience.

I had long suspected that from of all the various types of car or truck racing one could participate in, rally would be the most fun for me. It’s the ultimate symphony of speed, vehicle interaction, environment, and complexities of control in a seemingly perpetual state of losing control. We were not two days into the program before my friends were already talking about when we could come back for the advanced program. (Faster, more dangerous, more technical, and of course, more fun!)

As the experience drew on, I realized parallels between my professional life and the cockpit experience. I have always been a fan of applying lessons from one axis of life to another, so naturally my mind went to work. In fact, I got so lost in thought at one point that I had one of my instructors call me out. And there it was: my first life and business lesson gleaned from driving a heavily modified Subaru rally car through mud and snow in a way that would have earned me a trip to jail if attempted on the street.

“You’re thinking too much!” It was the only feedback I heard from my instructor on the second day as I tried to apply everything I had learned on day one. I was trying – all at the same time, for the first time in a car – left-foot braking, trail braking, throttle steering, late apexing, looking through the turn, turn-clutch-brake-release-throttle, and more. To top it all off, I had to navigate through mud, snow, gravel, hairpin turns and long sweeping turns in both directions, as fast as possible! How could I be thinking too much, when there was so much to think about?! But trying to memorize and analyze everything I had learned and apply it to every second of the course proved a disaster. I only frustrated myself and my instructor.

“Just relax and let your instincts take over,” he told me. “You already know what to do – trust and let it happen.” So I did. What a difference! Immediate, significant improvement, and so much more fun.

How many times do we find ourselves overthinking a problem to the point that it impedes our progress? Obviously, there is a time for analysis and deep thought, but this can have a negative impact if left unchecked. Sometimes you have to simply trust that you have all the tools necessary to find the right path. You just need to let go, trust, and let your instincts guide you.

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What Keeps a CIO Up at Night?


It might be easier to ask, what doesn’t keep a CIO up at night? And the answer is: not much.

First, and this may go without saying, there are multiple spectrums on which CIOs exist. Most have risen through the ranks of technology, while a few have an “other” background like operations, marketing, finance, or business. Many are forward-thinking and innovative. Some aren’t. Some work for companies which are forward-leaning and looking to digitally transform. Others don’t. Thus, the questions that keep a CIO up at night are deeply personal and tend to vary from one CIO and company to the next.

All companies rely on technology to some extent for their success, and more and more companies depend on it heavily, at an increasing rate. This creates a natural pressure applied to the technology leadership of a company to lead and not just to react. Technology executives are being asked more and more to play a more significant role in the leadership and future growth of their organizations, rather than just to keep the technology lights on and put out technology fires. 
If we accept this basic premise, then there are three macro struggles that are of significant concern to CIOs:

  • awareness of the business aspect of the company
  • the unrelenting rate of change with technology, and
  • being an effective leader in a dynamic era in which tech has the most important seat at the executive table

Business Savvy

Many CIOs simply do not have the same level of business acumen as they do technology prowess. That’s not a knock on the CIO community, and I don’t even believe it’s really a problem – it’s actually an incredible opportunity. Most CIOs came up through the technology ranks and are now working hard to bring their business awareness up to speed.  This is more than just general business sense and understanding of things like marketing, operations, sales, and how they interconnect. CIOs build a deep understanding of the actual business of the organization they are helping to lead, making sure their intimate knowledge of that business is applied to their strategic efforts on the technology side.  

There are excellent programs available (happy to recommend offline to anyone interested!) from University business schools, tech/leadership consulting firms, and other third parties, to help bridge this gap and develop additional business skills.  

Changes in Technology

The changing environment for a CIO also presents a complex challenge from a leadership standpoint. Many CIOs are transitioning from managing a technology team to leading a business in part by leveraging that technology team. This requires both cultivating new relationships with executive peers and a continued commitment to progress on the technology side of things so that everything can function smoothly. There is no end to the leadership and interpersonal effectiveness training opportunities here: no shortage of programs available to address these needs. There is also an organizational health component to this. When effectively implemented, it makes life a whole lot easier not just for the CIO, but for the entire organization they serve. Folks like The Table Group Consulting have world-class, proven methodologies for addressing these needs.   

Effective Leadership for the Brave New Business World

Finally, thanks to the blistering pace of change in the technology landscape, CIOs are being pulled in many new and different directions. It’s not simply only the compounding effect of billions of dollars flowing through venture capital firms into thousands of startups every year. CIOs are constantly trying to sort through relevant trends, companies, and technology solutions with long-term viability to a CIO’s specific needs. In short: the CIO’s tech leadership role has become infinitely more challenging. I’ve met CIOs with billion-dollar annual IT budgets, thousands of employees, but no one person (let alone group) dedicated to understanding the needs of the business. These needs include: building innovative relationships, researching the market, building a vetting process, filling the top of the funnel, building an adoption methodology, testing what emerges from the bottom of the funnel, and effectively implementing the right solutions.

Thankfully there are answers here, too. The venture community is starting to offer more avenues for CXO connectivity into relevant technologies. And to be fair, some top tier firms like Sierra, Greylock and Lightspeed have been doing this with excellence for some time.  Having seen the potential benefit of CIOs prioritizing the right innovation, my own company, The Syndicate Group, was formed to address this challenge for CIOs by aggregating all of enterprise tech innovation at the top of the funnel. This nearly eliminates the chance of a CIO missing out on a startup or technology solution that could make a dramatic impact on their business. Are there plenty of things to keep a CIO up at night? Sure. But there are also lots of great options available to quiet those anxieties, making for a very restful sleep.  With these resources in hand, the question for each CIO then becomes: how well do you sleep at night?

I’d love to hear about your experiences in the CXO environment! Post a comment here below and let me know what’s keeping you up at night or the methods you have found to address these challenges.

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