The Great Resignation & The Future Of Work: Greg Wilson On How Employers and Employees Are Reworking Work Together

An Interview with Karen Mangia

Karen Mangia
Authority Magazine
Published in
8 min readDec 30, 2021


The mix of remote work to in person. In the last 2 years so many employees worked remotely. Companies allowed that because they had to. As restrictions ease up what will the ratio look like? What companies will come out ahead because they learned how to keep remote workers happy, and to recruit globally?

When it comes to designing the future of work, one size fits none. Discovering success isn’t about a hybrid model or offering remote work options. Individuals and organizations are looking for more freedom. The freedom to choose the work model that makes the most sense. The freedom to choose their own values. And the freedom to pursue what matters most. We reached out to successful leaders and thought leaders across all industries to glean their insights and predictions about how to create a future that works.

As a part of our interview series called “How Employers and Employees are Reworking Work Together,” we had the pleasure to interview Greg Wilson, CFA.

Greg Wilson is a Chartered Financial Analyst. He recently retired from a 22 year career in Financial Services at age 42 to spend time with his wife and 3 kids 4 and under. He and his stay at home wife Erin run and

Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today.

I am a son of a father whose favorite child growing up was a business he started. I didn’t want that for my children. I wanted to be a more present father than I had. So at age 20 I developed a plan to retire in my 40s so I could spend time with my kids. My plan was a combination of owning rental houses and maxing out my 401k. I am 42 now with 3 kids aged 4 and under. My plan was to resign somewhere between age 45–50, but the COVID world accelerated my plan and I joined The Great Resignation.

Let’s zoom out. What do you predict will be the same about work, the workforce and the workplace 10–15 years from now? What do you predict will be different?

Things will normalize. Things always normalize. Many people want live human interaction. The government will also decrease incentives to not work. But the opportunity for employees to work when and how they want through mediums like Uber and Fiverr will only increase. COVID isn’t causing the Great Resignation. It is merely accelerating the adoption of remote technology and the acceptance that we do not all need to work 8a to 5p.

What advice would you offer to employers who want to future-proof their organizations?

We need to re-think the employer and employee social contract. The days of pensions are gone. Employees are more portable than ever. They no longer are constrained to local positions. Employees are no longer constrained to 40 hour work weeks. Employers need to reassess their labor model. They also need to be careful with messaging and tweaking the model too much.

Employees are people. They can quit. It has just taken a pandemic for employees to realize that. But that leads to opportunity for the employers who can meet the needs of employees’ desire for flexibility.

What do you predict will be the biggest gaps between what employers are willing to offer and what employees expect as we move forward? And what strategies would you offer about how to reconcile those gaps?

Hopefully the biggest gap isn’t solved by employers paying more. Not many employers can just pay more to make people happy. That will cripple the global economy if the larger firms just start paying more to retain talent. Instead employers need to understand the real issue. Employees are people. People like flexibility. In general people like their flexibility within some level of rules and guidance, as opposed to being left to come up with options. There are also many people being overworked and many others underperforming. Maybe it’s time to shift to pay for performance instead of pay for time. People want their time. Companies want performance. The best strategy may be switching to a low base salary plus pay for output. It’s better for employees, and its better for companies. But it’s hard for managers to figure out, because it puts the burden on them of understanding what is really needed vs filling 40 hours with work.

We simultaneously joined a global experiment together last year called “Working From Home.” How will this experience influence the future of work?

Working remotely has clearly accelerated people realizing they can have flexibility. It has also caused burnout. People are working more hours and producing more than they have in the past because they are handcuffed to their computer. For companies that work on Zoom it’s even worse. There are so many meetings now, and so much multitasking in the meetings. People are expected to be present in the meetings, still answer emails, and still produce. There isn’t enough time in the day. This is a problem that needs to be addressed as expectations of output are high. Skepticism that peers are working is also high.

Related, the meeting fatigue was one of the main contributors to me leaving my career in Financial Services and instead living off income from and rental houses. I just became worn out at how many meetings we had without getting anything done. I decided my time was better spent with my kids, and the high income wasn’t worth spending my life in meetings.

We’ve all read the headlines about how the pandemic reshaped the workforce. What societal changes do you foresee as necessary to support a future of work that works for everyone?

I was just talking to a friend about this on a run a few days ago. Many people resigning and many others working as freelancers is creating a true retirement funding problem. Are these people funding their retirements? How will social security be funded if so many fewer people are working? These are really big looming bubbles. Perhaps employers can incent employees back by offering incredible retirement packages. I struggle with how people will fund their retirements.

What is your greatest source of optimism about the future of work?

I am very excited that work should become more efficient now. So much time is wasted at 40 hour a week jobs. The work flow is often a roller coaster. So much downtime is wasted, and in that downtime employees are either working on things that don’t matter or surfing the web, handcuffed to the appearance of working. Now we should be able to evolve away from 40 hour a week jobs and instead into pay for doing what’s expected.

Our collective mental health and wellbeing are now considered collateral as we consider the future of work. What innovative strategies do you see employers offering to help improve and optimize their employee’s mental health and wellbeing?

I see this as a fascinating area. The better companies will find ways to have employees feel like there is a balance. The ok companies will ignore it all together. The lessor companies will try too hard to do this and employees will see through it, but its such a sensitive topic that the employees won’t speak up and acknowledge that they see through the disingenuous attempts.

What this really means is a new niche will arise in Human Resources.

It seems like there’s a new headline every day. ‘The Great Resignation’. ‘The Great Reconfiguration’. And now the ‘Great Reevaluation’. What are the most important messages leaders need to hear from these headlines? How do company cultures need to evolve?

That it’s Great, and that it’s evolving.

Let’s get more specific. What are your “Top 5 Trends To Track In the Future of Work?” (Please share a story or example for each.)

  1. The mix of remote work to in person. In the last 2 years so many employees worked remotely. Companies allowed that because they had to. As restrictions ease up what will the ratio look like? What companies will come out ahead because they learned how to keep remote workers happy, and to recruit globally?
  2. How many people will not return to the workforce. The Great Resignation is real. But it isn’t the Great Retirement. How many people are going to go back to work and when. If they don’t then who is funding social security? Who is funding the retirements of the younger Great Resignationers?
  3. How platforms like Fiverr will continue to pressure test the traditional structure. I feel the pandemic only accelerated the inevitable. Platforms like Uber, Instacart, and now Fiverr are legitimate threats to the traditional employer/employee social contract. Which platforms will thrive? How will large companies adapt? Will they start sourcing talent from Fiverr? How will that impact consulting firms?
  4. What creative flexible feeling benefits will employers offer. My cousin is a nurse. She explained to me that she can just get on an app and choose when she wants to work. The app says how much and what hours are available, and some other good to know things. Her employer is in both St. Louis (where family is) and in California (where her boyfriend lives). So she can be portable. Obviously there are challenges for an employer with this arrangement, but there are also benefits. This is something I think should see more adoption.
  5. Will the cost of living differences throughout the country, and world shift the population?. Will more people leave large cities and move to smaller ones now that they can work remotely? Now that companies can hire people outside of their own local market, how will that smooth out the salary differences in different cities? If a company is headquartered in Chicago, why pay someone Chicago salary if that person lives in Belle, MO? This could put pressure on salaries in large cities and elevate smaller cities? If these dominoes fall then smaller cities will have large tax bases. Remote work may improve the standard of living for so many people that now have access to positions they didn’t have access to, and for companies to now have access to less expensive but equally talented resources.

I keep quotes on my desk and on scraps of paper to stay inspired. What’s your favorite “Life Lesson Quote”? And how has this quote shaped your perspective?

“It doesn’t matter who is wrong or right, it only matters what is right.” I don’t understand why we all have a need to prove how smart we are. It’s hard but I try to let go of that and focus on “what is right”, now “am I the one that is right”.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment 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, and why? He, she, or they might just see this if we tag them.

Mark Cuban. Back before anyone knew who he was, and before anyone knew what a blog was, he had one. We exchanged emails a few times back then. I was in my early 20s and struggling with how easy MBA coursework was and it seemed pointless. I asked him his thoughts, and he said something to the effect of letters don’t matter, it’s what you know that matters. So I dropped out of graduate school and bought 8 houses (with $800!). That led me to retiring from Financial Services at age 42.

Our readers often like to continue the conversation with our featured interviewees. How can they best connect with you and stay current on what you’re discovering?

My wife and I are both stay at home parents now. Follow us on your favorite social media @ChaChingQueen and visit our sites and

Thank you for sharing your insights and predictions. We appreciate the gift of your time and wish you continued success and good health.