Companies are getting smaller and more efficient — With tools and technologies, most companies don’t need the infrastructure and the number of people that they used to need to get the same work done. A lot of this is driven by AI and machine learning.

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 Sam Rosen.

Sam Rosen is the co-founder of Deskpass, a Hybrid Work solution for companies with remote or distributed teams. Sam emerged as a leader in the space in 2009 when he opened the Coop, Chicago’s first coworking space. Since then, Sam has dedicated his time, energy, and talents to Deskpass, a Hybrid Work solution for companies with remote or distributed teams.

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.

The birth of my first child was a complete life changing, transformative experience for me. I’ve always been a workaholic and very entrepreneurial and very driven. I realized quickly after reading a book in my kid’s room and spending time with him as an infant that this seems a lot more important and meaningful than all the work that I do. Perhaps, the meaning of a happy life has nothing to do with work and has more to do with being present and being with your family and people that you love.

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?

The first wave of adopters was on the early edge of remote work and were solving for their own problems. As that grows, and more people adopt these types of spaces and over Covid, realizing that employees can work remotely and be productive and I have expensive real estate that isn’t flexible. It’s exciting to see how big and how fast and how huge an industry can change. The next big phase of this world is having workers who have worked at a company for 25 years, worked at the same office for 25 years, and this will be their first-time walking into a coworking space. Even though this has been going on for 10 years, we’re still at the very beginning of this. The big adoption we’re going to see over the next 10 years is going to be the everyday person in the suburbs. It’s exciting to watch the world evolve and the toolset evolve, and the industry evolve. It’s been humbling and amazing and a once in a career opportunity.

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

It’s time to let go of the old paradigm of the office. In the future, employees are going to have the upper hand and they are going to drive this change in how we work. Think of the office as an ecosystem. The HQ isn’t going anywhere but it’s going to be smaller and more specialized and there isn’t going to be a desk for everyone. Give your employees the ability to work from wherever they get their best work done. That might include their home, or other places like coworking spaces and other types of environments. Don’t fight the change. Instead, give your employees tools and enable them to get their best work done wherever they’re working.

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?

To hire and retain and attract the best employees, you’re going to have to offer flexibility. It’s time to rethink the 9–5 workday and the 5-day workweek. The best employees are going to have the ability to work from wherever they want. If they’re comparing a job between two employers that have the same title, same prestige, same compensation, they are going to work for the company that gives them the freedom and flexibility to work where they want to.

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

This is an exciting change. Allowing people to work from where they want to work will re-shape where people live and what cities are made of. If you think about the long-term consequences of allowing autonomy and freedom to work where you want to work, I really think this is going to re-shape more than just the office. It’s going to reshape the suburbs, and cities outside of big, central business districts. These changes are going to reshare transportation, food, dining, telecommunications, and travel. It’s really exciting how much can change when you’re no longer tethered to be in a certain proximity to the office.

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?

If we’re going to build a future where employees can work from wherever, then companies are really going to have to re-shift their communication practices and how they organize and how they work together to the lowest common denominator. So, instead of that one person who’s remote being the outsider and having a sub-par experience, organizations and companies in the future are really going to have to build a culture and processes that are hybrid-first or remote-first that make it easy for folks to get their best work done.

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

If we no longer must build our cities, our families, our lives around where we work and being in proximity to that place, that creates a lot of freedom for folks to travel, for them to be themselves and ultimately be happy. I think the other thing that’s exciting is that people who weren’t offered an opportunity in the first place because of where they live or the type of biases you get around geography. It really creates a more global world where people get to work with people with all sorts of skills, backgrounds, experiences that will ultimately make a world a more beautiful place and create a more beautiful tapestry of ideas since we’ll get to share more across the traditional restrictions we’ve had in the past.

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?

As companies engage with tools like Deskpass and give their employees more autonomy to choose where they work, the best companies are reinvesting the huge cost savings they get in not having to have real estate for everybody, back into their employees. This often means all sorts of wonderful benefits and perks that can be around health and wellness. Making sure that their employees have things like gym memberships, CSAs, mental health allowances for therapy or counseling. The most interesting companies are reinvesting the money that they save that they used to put into the desk that sat empty most of the day and they’re thinking of their employees much more holistically and trying to offer them tools and resources and techniques to have not just a more efficient workday but a more well-balanced life and ultimately more work-life balance.

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?

I don’t wholesale buy the whole ‘great resignation’ period. Most people want to find purpose and meaning in their work, and I think what we’re seeing is people who have had crappy jobs and were not compensated fairly and felt unsafe or uncertain, are just saying ‘no’ and moving on from that lifestyle. If you are a great company that does good things and takes care of their employees, then there’s never been a better opportunity to find incredibly gifted, talented people, especially now that most companies are no longer limited by where their office is and can find fantastic people all over to do those jobs.

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

  1. The office is an ecosystem — The office isn’t going anywhere but companies are going to offer a network of spaces to work and access to all sorts of tools and places to get that work done.
  2. Health and wellness are going to be a huge component in how companies incentivize their employees. — They are going to think more about the big picture and the entirety of a worker and not just what they do when doing their job.
  3. Globalization and the ability to hire people from all over. — Companies are going to remove their hiring restrictions around just hiring around their office. We’re going to see more companies work with more people in the suburbs, rural environments, across the pond.
  4. Coworking spaces are going to be much more driven by food and beverage. — We’re already starting to see this with the Hoxton hotel and other innovative brands. We might see people picking their workspaces just like they make lunch reservations. The food and the vibe piece is going to be more important to me than ever.
  5. Companies are getting smaller and more efficient — With tools and technologies, most companies don’t need the infrastructure and the number of people that they used to need to get the same work done. A lot of this is driven by AI and machine learning.

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?

One of my favorite quotes is ‘luck is the residue of design’, which is a Branch Rickey quote. I love how simple and beautiful this is. The most successful people that I know and the luckiest people that I know, it didn’t happen by accident. The folks that consistently put themselves in the right situation and do the right things and get themselves in the right rooms are the folks who get the best outcomes.

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.

There’s a lot of people that I’d really love to get to know. As a Chicago boy, I’ve always been tremendously inspired by Barack Obama and his campaign and how he ran for office and approached the office and I’d love the opportunity to sit down with him. I’d also love to meet Laurene Powell Jobs and learn more about Steve. I grew up ditching school and faking sickness to watch Steve Jobs do his keynotes.

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 website, Sammy Rosen, is probably the best place.

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