Benefits will become more compelling. Baseline benefits that existed pre-pandemic won’t cut it for most employees. Companies will need to research and understand what benefits people are looking for in a remote-first workforce. Expect that benefits will evolve beyond traditional PTO models to include options for sabbaticals, flexible living, and subscriptions to communities and platforms to help employees connect to what matters most to them.

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 Rachel Azaroff.

Rachel Azaroff is the Founder and CEO of 312 Society, the platform for remote workers, sabbatical takers, empty nesters, and newly retired people to design their lifestyle and build community.

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 was an elite swimmer from ages 10 to 20. I trained year-round and competed regionally, nationally, and globally. Starting at age 10, I had practice six times a week. In college, I trained 20 hours a week. Swimming is both a team sport and an individual sport. Ultimately, you are competing against yourself and the clock. You train for hundreds of hours for a race that is under one minute and you can win or lose by .01 seconds.

I see a lot of parallels between being a competitive swimmer and building a startup. You are both competing in your market and against yourself. Building a business is a marathon, not a sprint. In certain seasons of the business, you have a key priority and let other things go, similar to preparing for a major swim meet and making sacrifices to be in top shape.

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?

When I think about what will be the same about work in 10–15 years, I think there will continue to be a focus on company culture and creating connections within the workplace. Employers are investing heavily in their company cultures today and I believe that investment will only increase over time.

What will be different a decade from now is how companies look at performance. For the most part, the days of sitting at a desk from nine to five are gone. We will see companies shift toward a performance evaluation system that focuses on outcomes that are benchmarked against clearly defined goals. My hope is that the workforce will become more equitable as performance expectations become more aligned with the realities of work in the digital age.

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

In the post-pandemic era, you cannot go back to the culture and environment you had before. If you try to force employees back into an environment that was designed for a pre-pandemic society, you will lose.

Today’s job market is owned by employees, so it’s more important than ever for employers to be actively listening to their employees and acting on the data they have at their disposal.

Remote work will continue to be a requirement for many employees, so offering flexibility will be key. However, it’s important to note that flexibility in a remote workforce could mean more than having the ability to work from home. For example, a big focus for many during the pandemic has been on care — childcare, eldercare, family leave, etc. The needs for dependent care and family time have evolved during the pandemic and companies need to be aware of that.

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?

There are still employers that are set on bringing employees back into the office full-time even though their employees are asking for remote or hybrid work options. This disconnect will continue to be a major gap for some employers and will ultimately lead to mass resignations.

Employees have reclaimed time previously spent commuting and sitting in the office to better design their day around their needs and priorities. They now have time to workout, spend time outdoors and be with their families. When people are happier, they are more engaged and have stronger performance in their careers.

For these employers, my advice would be to focus on reconciliation. Grant flexibility for employees who seek it, change the way your company looks at KPIs and performance, etc. All in all, the pandemic has taught us all the values of flexibility and empathy — employers will need to keep these in mind as we move forward.

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

The world went remote overnight. For some, it was a jarring experience filled with ongoing pressures from work, the added stress of having children at home, and more. For others, it was a welcome respite from the demands of commuting and being in the office every day. Regardless of everyone’s personal experience, the global work from home experience fundamentally changed the fabric of the professional world for good.

We’re already seeing this unfold today — more companies are going fully remote, easing in-office policies, and more. Flexibility will define the future of work and I believe that employees will only continue to demand more flexibility as they seek to find an even better balance between work and life.

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?

  1. Employers assisting with care — Whether it’s childcare, eldercare, or more flexible leave policies.
  2. Achieving equity and parity by moving toward outcome-oriented performance measurement that is applied in a consistent way.
  3. Moving away from an HQ office and toward employer-sponosored coworking memberships where employees can go into an office when/where they want to. Also, companies should provide stipends for employees to travel and gather in locations convenient for themselves.
  4. Employers collect and implement real-time data from employees about their needs and preferences. The days of companies using an annual employee engagement survey that takes 6–9 months to acknowledge and implement findings are over. Employees aren’t waiting around that long for an employer to provide what they are looking for.

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

I’m most optimistic about the promise of a borderless workforce. We have more choices than ever before when it comes to how much work defines our lives. It used to be that much of our lives were defined by work — where we lived, what car we drove, how much free time we had, etc. Now, people have the opportunity to make jobs fit into their lives instead of vice versa.

I believe that as the workforce truly embraces the possibilities that come along with being borderless we will see an increase in happiness, a reduction in burnout, and an overall increase in productivity. If employees are happy, it will shine through in their work.

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?

  1. A focus on outcomes > sitting at a desk for set hours. When people align on outcomes and have autonomy on how they manage their time, they can infuse more mindfulness and wellness into their day. Employers can assist with this by making this a part of company culture, leaders sharing how they are doing this, and paying for tools to help with this such as Calm, Headspace, Peloton, etc.
  2. Sabbatical programs. Pre-pandemic, 1 in 5 U.S. employers offered a company-sponsored sabbatical program. I believe and hope to see more companies offering sabbatical programs. These programs are a great recruitment and retention tool. They also meaningfully contribute to employee wellbeing and add to their inspiration and spark.
  3. Having tighter controls and boundaries around roles, responsibilities, and expectations. Boundaries between work and life faded leading into and through the pandemic. As a result, people have been “on” and working more than ever — leading to burnout. There is a lot of inefficiency in the workforce and ambiguity around who is doing what. By clarifying roles, responsibilities, and how success is measured, employees have more autonomy over their time and can align their work in a way that works for them in the context of their larger life.

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?

All of these headlines culminate in a trend some are calling “The Great Realization.” People are realizing that the age-old way of doing work just doesn’t work in today’s society. Employers need to hear their employees loud and clear and make changes today — not down the road.

I’ve talked a lot about enabling a more flexible work environment, which is where many companies need to start. From there, companies need to give more thought to how their employees’ work fits into the broader spectrum of their lives. It’s there that companies can better support their employees as the “real people” they are. Some ideas could include offering sabbaticals or extended leave benefits, stipends to allow employees to live in different locations, quarterly meetups for remote employees to connect with others in the company, and more.

It’s not just about allowing employees to work remotely, it’s about enabling them to live remotely. Contributing to the other areas of their lives will have a positive impact on the value they provide to the business.

Many companies serve a global audience — giving your employees an opportunity to immerse themselves in new cultures and places is good for them as an individual and adds to their perspective on how they approach their job.

Let’s get more specific. What are your “Top 5 Trends To Track In the Future of Work?”

  1. The focus will shift toward outcomes. Employees shouldn’t be expected to sit at a desk under the watch of management. Companies will continue to shift their focus toward outcome-based performance and rewarding employees that make an impact based on set goals. Gone are the days of rewarding employees for being physically present from nine to five.
  2. Benefits will become more compelling. Baseline benefits that existed pre-pandemic won’t cut it for most employees. Companies will need to research and understand what benefits people are looking for in a remote-first workforce. Expect that benefits will evolve beyond traditional PTO models to include options for sabbaticals, flexible living, and subscriptions to communities and platforms to help employees connect to what matters most to them.
  3. The definition of the office will evolve. A remote-first workforce will likely lead to some companies moving away from the costly overhead of corporate offices. However, companies will still need to create ways for employees to come together in real life. As organizations truly embrace remote work, they will need to invest in ways for employees to cowork — whether it be through stipends, subscriptions, etc.
  4. Investments in learning and upskilling will increase. The pandemic ignited a desire for further education and training in many people. The way people learn and earn credentials is up for debate post-pandemic and higher education is on track for a major makeover. As such, corporate training needs to evolve. People want to learn new things and evolve and grow in their careers. This is another example of employers needing to ask employees and listen to their answers on what and how they want to learn to continue to evolve in their careers while meeting the evolving needs of the business.
  5. Career breaks will be common. The career model that has existed for decades was one that was designed to serve the greatest generation — a group of people that benefited from pensions and long-term commitments to companies. In 2022, people are still working off this model that no longer works. The norm of working ages 22–65 and taking one week of consecutive time off a year, perhaps two weeks, and waiting until retirement to fulfill that bucket list dream — does not make sense today. People are working more than ever with the rise of technology and global workforces. Most people cannot afford to retire at 65 and people are living longer. We will see employees look for more opportunities to press pause and take time to invest in themselves, address burnout, and more. Sabbaticals, increased leave, and other flexible time off options will help support employees and protect their wellbeing.

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?

My dad always says, “You can’t soar with the eagles if you fly with the turkeys.” I think about this quote a lot. It matters who you surround yourself with and it is important to set your intentions.

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.

Arlan Hamilton — I admire what she has built with Backstage Capital and Runner. I read, “It’s About Damn Time” and was inspired and motivated. She is a trailblazer who is charting her own path and showing the world that there is room for different approaches. She is authentic and shows up in a consistent way.

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?

You can connect with me on LinkedIn at ​​ or follow me on Twitter at @AzaroffRachel. You can also email me at [email protected].

To connect with 312 Society, visit

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