Rising Through Resilience: Michael Gardon of Rejoin Media On The Five Things You Can Do To Become More Resilient During Turbulent Times

An Interview With Savio P. Clemente

Savio P. Clemente
Authority Magazine


Managing risk and uncertainty is a critical skill for the future. The world changes fast, and most of us don’t stick with one company or even one career. On the flip side, companies rarely show loyalty to their people in hard times, and every company will go through hard times. You are going to encounter problems and setbacks at a higher rate today than your parents may have a few decades ago, when things moved slower. So, your ability to scenario plan and deal well with uncertainty is key, even if you 100% know your path.

Resilience has been described as the ability to withstand adversity and bounce back from difficult life events. Times are not easy now. How do we develop greater resilience to withstand the challenges that keep being thrown at us? In this interview series, we are talking to mental health experts, authors, resilience experts, coaches, and business leaders who can talk about how we can develop greater resilience to improve our lives.

As a part of this series, I had the pleasure of interviewing Michael Gardon.

Michael Gardon is a former derivatives trader turned investor and entrepreneur. He is the CEO of Rejoin Media, a holding company for digital brands and businesses. Mike is also the Executive Editor and Host of the acclaimed Careercloud Radio podcast on Careercloud.com. Mike is an advocate of remote work and intentional work-life integration. He runs his teams remotely from the beautiful (and affordable!) Midwest, where he resides with his wife and 3 young boys.

Thank you so much for joining us! Our readers would love to get to know you a bit better. Can you tell us a bit about your backstory?

I’m one of those college people who had no idea what they wanted to do with their lives from a “career” standpoint. I distinctly remember a conversation with my father where he asked me what I was going to do. I said, “I don’t know what I’m going to do, but I have a feeling I’ll be doing lots of different things and I’ll be successful.” Since then, I’ve had multiple careers, from trading derivatives for a living (basically gambling) to trying to sell software and hardware designs to defense contractors to online media, to Fortune 500 innovation consulting back to where I am now in online media. Because the world is changing so fast, and since I didn’t have a clear path, I realized early that I needed to build a system and approach to “career” that helped me deal well with uncertainty and change. From the outside, my path can look haphazard, but curiosity, investing and entrepreneurship have been the common threads woven through all of my experiences, and I use them all today to build an intentional work-life that works for me and my family. Through my work with Careercloud and my own writing I’m trying to lend my experiences to help people understand their options, create a process for exploring those options and build an intentional work-life, that is both ambitious and resilient.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

In 2012 after my first startup’s failure, I started a freelance consulting company basically just to make ends meet. I wanted to work with startups again, but was moving to a smaller town (and this was pre-remote work) I didn’t have a good sense of which company or opportunity would take off. So I leaned on my finance background and figured I would create a small portfolio of opportunities by getting 3–5 clients. I figured this might be more work, but I would gain valuable signal on which opportunity would grow faster and be best for me. With this knowledge, I could “bet bigger” on the winning horse by either committing more time or even going full time with that company, which I ended up doing by joining the team at Reviews.com as the fifth full time employee with equity. We went on to build a high growth team, and that company ended up being acquired by private equity a few years later.

While this may seem like a rather mundane story, this was the early days of freelance consulting. There are so many nuggets here that are valuable to understand from a resiliency standpoint.

  1. Managing risk and uncertainty is a critical skill for the future. The world changes fast, and most of us don’t stick with one company or even one career. On the flip side, companies rarely show loyalty to their people in hard times, and every company will go through hard times. You are going to encounter problems and setbacks at a higher rate today than your parents may have a few decades ago, when things moved slower. So, your ability to scenario plan and deal well with uncertainty is key, even if you 100% know your path.
  2. To deal well with “not knowing” you need to increase options. When you “know” you need to decrease options. The default state of the world is that not everything works out. So, if you are not sure of your path, then you need to start multiple paths. These are called options. As you gain information about these paths, you become surer of a particular path and you can decrease options to increase your focus.
  3. Arm’s length employment is good for you. Freelance consulting is a great way to gain career options without drinking the Kool aid of any one company. The relationship keeps you at a distance from your clients that helps you keep a wider view perspective. This increases your options and freedom. Plus, it forces you to think like an owner.
  4. The easiest way to be valuable is to go where there is high demand and low supply. Startups consume talent at a very high rate, and in their infancy, there is often just a need for bodies that are capable. So, if you haven’t figured out your one talent or your passion, startups are perfect for learners and jack-of-all-trades people to start.

What do you think makes your company stand out? Can you share a story?

We stand out because of our philosophy. The name of our company, Rejoin Media, comes from our small group of employees who have worked together in the past coming back together and “rejoining”. But it also is about all of us getting back to or “rejoining” our roots as people, and reconnecting with what is most important to us. Universally, within our small team, is a desire to not overcomplicate and not be too big because that allows us time and energy to live great, integrated lives where we are challenged to grow and make a big impact on the people we care about.

There’s a mantra in startupville that goes like this, “the easiest way to make a billion dollars is to help a billion people.” I disagree with that. I’d rather have an outsized impact on a small number of people. That’s how you build loyalty, bonds and friendships that last a lifetime.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

This is hard for me. I feel like I’ve been on a lone career journey that most of my peers and friends don’t really understand. I would say my dad has helped me the most. We are similar in many ways, but we approach risk differently. He’s a lawyer who has been on one path his whole life, and he has been very successful. He’s very risk averse. He knew what he wanted to do and executed relentlessly. On the other hand, I’ve already had multiple “careers” and take a decent amount of financial risk trading and investing. I always worry about what he thinks of my choices. To his credit, at every juncture in my life, he’s been nothing but supportive, and this was a big weight off my shoulders that allowed me to go forward past discomfort.

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the trait of resilience. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Resilience is the ability to deal well with uncertainty.

Resilient people are wayfinders. They don’t need to see the future, they find their way. I think resilient people tend to not be over-optimizers. They understand that there is vastly more that they don’t know than what they do know, so they are extremely humble. They’re not worried about being offended or being wrong. They practice delayed gratification. They spend time thinking about, and planning for outcomes that can vary from what is ideal. This means that they are able to maintain a wider perspective, but not be overwhelmed with every possible outcome. Lastly, they are simple. Simple is robust, complexity is fragile.

Courage is often likened to resilience. In your opinion how is courage both similar and different to resilience?

I think of resilience as systems and mindsets put in place to deal with uncertainty. I think of courage as the ability to act in spite of uncertainty. So, certainly these go hand in hand, but they are different. You need systems set up because you often can’t think straight in extreme uncertainty. This is why Navy Seals perform the smallest task over and over and over until it becomes second nature — precisely so they don’t have to think.

I think most people who systematically think about resilience do so out of fear. The best risk managers on Wall Street are hyper focused on not losing money. The best entrepreneurs are always focused on managing downside risks. This can be anxiety provoking, but the act of systematically thinking about uncertainty is itself courageous because you are honestly saying that there is a real probability that some bad thing can happen, and you are taking proactive steps to mitigate that risk or create plans to otherwise deal with it. Courage, then, is acting on your best course of action, even if it isn’t a perfect choice.

Becoming more resilient only entails thinking through the next branch of the decision tree, and having a clear headed view of the options you have at that juncture. Then, if that problem comes to pass, act on your plan. It may not be perfect, but you will definitely be in a better spot than if you never thought it through at all.

When you think of resilience, which person comes to mind? Can you explain why you chose that person?

Ray Dalio the famous hedge fund manager and Elon Musk, but for two different reasons. Ray Dalio has spent a lifetime thinking about how to manage risk and deal well with uncertainty, so I think he is the preeminent example of systematic thinking to making sure he never gets knocked out of the game. I’ve read all of his works and I even have a pdf copy of his ‘Principles’ which he later turned into a book. It is required reading for anyone wanting to understand how to deal well with uncertainty.

I think Elon Musk is resilient because he is surprisingly simple, and it seems like nobody really understands this about him. Right now he’s the world’s richest man, but his identity is not wrapped up in all of that. He’s focused on building things for humanity that he thinks are most important. He has very few posessions to bog him down so he can be nimble. And he’s got courage. At one point he had both Tesla and SpaceX at risk of insolvency at the same time. He was sleeping on friends’ couches because he put all his own money (hundreds of millions at the time) back into the companies. It ended up working out and he came back from that bottom period, but it easily could have gone the other way.

There’s also a great story about Elon having dinner with Charlie Munger (Warren Buffett’s business partner). Charlie was rattling off all the ways that Tesla wouldn’t succeed. Without getting upset, Elon agreed with all of them, but responded that it should be tried anyway!

If he had a complex psyche that was wrapped up in what people would think if he lost it all, he never would have made those moves and ironically, he would have lost it all.

Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us?

I don’t think anyone has used those words, but I’ve definitely thought some things were close to impossible, and I’ve had people encourage me to give up. Most people think completing an Ironman triathlon is crazy if not impossible, yet thousands of people do it every year. I was fortunate enough to train for and complete a few. What I learned through that process was that actually anyone can do it. The separator is simply your obsession with going through all of the process and taking all the painful steps to be able to do the race, which is 140.6 miles. I was lucky in that I was so obsessed with doing it that none of that was an obstacle for me. I actually enjoyed the process of breaking this huge, scary thing into small steps each day. Training for hours by myself was cathartic.

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

My first startup failed. I felt horrible because I raised money from close friends and family and it was all gone. I was depressed, had a young child at home and we were moving states. I had no plan, but I had been doing some thinking about the power of financial options, how they are used and where their value comes from. An option is the right, but not the obligation to do something (or purchase something) at a future time. This costs a small fee up front, but allows you the ability to acquire more information in order to make a larger decision in the future. Land options are used a lot in large real estate deals. If a company can’t put a deal together, or the economy tanks, they do not have to buy the property.

I decided that in order to even create a plan, I would need to figure out how to produce a portfolio of options. For me, this meant I would start a remote consulting business focused on helping startups in the early stage. Within a couple of months I was making more money than I had previously, and by having several clients I secured an option on all of them whereby if I did good work, and one started to take off, I could choose to join them. My client, Reviews.com began to take off and I was hired as the 5th full time employee. I eventually lead a business unit and we were acquired by a private equity company.

I didn’t know the future, and didn’t know which path would lead to success, but I created several options, found which one was working and then placed a larger career bet as I gained more information and certainty.

How have you cultivated resilience throughout your life? Did you have any experiences growing up that have contributed to building your resiliency? Can you share a story?

I became much more conscious of resiliency in adulthood once I got out into the real world. I got out of college during the dot com bust, and then I was a trader during the housing bust. So I lived through two significant panics in my 20’s. It became very clear to me that the ability to adapt quickly would be a superpower moving forward. To adapt, which is a huge part of resiliency, I needed to set up systems, diversify my options for approaching life and take an honest approach to prepare for worst case scenarios like losing a job or my income completely. It was just a mindset born early by experience.

I think one way I cultivated it in childhood was through athletics. Athletics as a way of forcing adversity on you. Not everything goes your way. People are trying to stop you, and you have to deal with it and overcome it or lose, learn and get better.

I have three young children and I think a lot about how I can help them cultivate resilience. If you spend 30 minutes trying to understand psychology and Cognitive Behavioral Therapy it’s very clear that the path to resilience is programmatic exposure to stressors in a dosage that the person can handle, and increasing that dosage over time. So, I try to take that approach instead of shielding them from stressors which, unfortunately, is what I see most parents do these days.

Resilience is like a muscle that can be strengthened. In your opinion, what are 5 steps that someone can take to become more resilient? Please share a story or an example for each.

Yes! Resilience can be strengthened. We have a saying at our office: “Resilience is Brilliance.” Cultivating resilience involves two parts: training your mind and setting up flexible systems to deal with uncertainty.

Step 1: Start expecting problems

It’s a fact that you will constantly encounter problems, slights, communications difficulties with co-workers, setbacks and loss. The weak approach is to stick your head in the sand, or to expect everyone to see the world as you do. The courageous approach is to expect problems. One way to do this is through a pre-mortem. This exercise is used mostly within a team project setting, but can be easily adapted to any endeavor. Take a regular day for example. You could spend one minute acknowledging all the things that could go wrong or cause you stress. You will get cut off in traffic. You will get slighted at work. You will get triggered by something you read on the news. Your kids will yell at you. This is the reality state of your life. Waking up and starting the day as if none of these things will happen is making you inflexible to minor stressors.

The author and life hacker Tim Ferriss uses a similar process that he applies to his life called Fear Setting. This is simply looking at his life from a detached point of view and asking what are his biggest fears, or what is the worst case scenario. Only then can you determine if that scenario is catastrophic, or what steps to take to mitigate that scenario.

Step 2: Methodically expose yourself to stressors

Once you see the problems and fears you can expect on a day to day basis, you can start systematically exposing yourself and thinking about how to deal with them. Cognitive Behavioral Therapists use Exposure Therapy to help cure phobias and extreme anxiety. You can use this process yourself with any problem you’re having difficulty dealing with. For example, I use meditation and visualization to imagine dealing with a difficult co-worker. By visualizing the same scenario over and over I’m able to imagine how my co-worker will bother me. Over time, he will bother me less and less and I will develop better strategies to dealing with him that are productive.

Exposure to fear lessens fear. Less fear makes you more resilient. This is a scientifically proven fact.

Step 3: Create options

If I’ve convinced you to this point that problems are everywhere, unavoidable and mostly unknown, then the only way to deal with these uncertain problems is to create multiple options for how you will respond. The most effective tool for doing this is to use a process called “diverge/converge” which I’ve borrowed from the world of Design Thinking taught to me by world class design firm Ideo. We used this technique to build the first non-insurance business in the history my Fortune 500 client’s business.

Define the problem properly, suspend judgement, and admit that you don’t actually know the answer. Then, make a list of all the ways you could solve that problem (diverge). No possibility is too silly. Once you have a bunch of ideas out there, pick the top three that you have a hunch will be the most effective. Here’s the key, go one step further on the top 3 and define what next step you could take to test or get feedback as to whether you are on the right track with that solution. If you test 3 possible solutions, receive negative feedback on two of them and positive feedback on one of them, you have converged systematically around the best answer.

Having a systematic approach to both generating options and eliminating options is the key to dealing with uncertainty.

Step 4: Reflect and improve

This step is just a continuation of updating your knowledge set based on your experiences and feedback from the real world. Except, most people don’t systematically update! I use a quarterly process. I just set aside a couple hours each quarter to reflect on what went well, what caught me off guard or any changes that may be likely to occur.

Ray Dalio’s book Principles is just a continuous effort to reflect, improve and update thinking to be more resilient and get better results.

Step 5: Moderate the ups and downs

It’s important to maintain an even keel. When you choose to take risks in pursuit of great achievement you will experience highs higher than you can anticipate and lows lower than you’d like to admit. These points in time are emotionally taxing, but they are not a reflection of you or your worth. That stays constant. To moderate, I use another concept from finance called rebalancing. When I’m doing well, I try to imagine saving some of my good feelings and positive energy, and packing it away to use when times inevitably get rough again. And when I’m doing badly, I think about packing some of that negative emotion, energy and fear to use it at times when I’m riding too high. This helps me not get too carried away when I’m doing well, and helps stave off depression and anxiety when I’m doing poorly.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I want people to start investing in themselves from an earlier age. There are too many people too reliant on others to give them what they want instead of creating it. One of the biggest impediments is simply that people don’t know or can’t choose what to go after. I hope the antidote is a framework to figure that out which I’ve outlined above. But another antidote is simply to choose yourself over everything else. You’re responsible for making yourself happy and successful or whatever else you want, so stop worrying about what others think, get off social media and invest that time back into yourself.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them :-)

Ray Dalio — because I believe he is exceptionally thoughtful, modest and honest about what he does not know.

Elon Musk — because I’m in awe of his ability to try valiantly.

Jonathan Haidt — because his writing and book has greatly influenced how I approach raising my three children. I would like to thank him personally.

How can our readers further follow your work online?





This was very inspiring. Thank you so much for joining us!



Savio P. Clemente
Authority Magazine

TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor