Darcy Boles On How We Need To Adjust To The Future Of Work

Employee journey mapping. Some companies are already doing this, but just as most customer-focused companies map their customer journey, all companies should be mirroring it with the employee journey. We’ll see investment in employee experience design, employee archetype research, and a hyper-focus on building a workplace framework that allows for both autonomy and connection. When […]

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Employee journey mapping. Some companies are already doing this, but just as most customer-focused companies map their customer journey, all companies should be mirroring it with the employee journey. We’ll see investment in employee experience design, employee archetype research, and a hyper-focus on building a workplace framework that allows for both autonomy and connection.


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 Darcy Boles.

Darcy Boles is a Future of Work Thought Leader and Remote Experience Designer. Her deepest why is that work doesn’t have to suck, and she has dedicated her career to ensuring that it doesn’t.

Darcy was leading remote teams before it was “a thing.” She pulls her design architecture from global experiences and cultures from around the world, using positive psychology research to align company ecosystems with shared intrinsic values and experiences.

She believes that we all have the power to create a better world and live the lives of our wildest dreams when building flexible workplaces on a stakeholder mindset model. While she loves to travel and many would consider her a digital nomad, she spends most of her time in San Diego with her fiancé Dan, Golden Retriever Blanche, and a quiver of surfboards.


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.

Thanks for having me!

I’ve always been someone who has danced a bit to the beat of my own drum, so when I took my first office job in Silicon Valley I wasn’t quite sure what to expect, and looked at it through the lens of a grand adventure. While I thoroughly enjoyed traveling for work and the creativity + innovation of a high-growth tech start-up, I didn’t love having to come into an office in a busy city center everyday. Frankly, I just didn’t understand it. Because I didn’t have the autonomy to really design my life around my work vs. the other way around, having to be in the office every day or traveling on a weekly basis, caused me to get caught up in putting “the hustle” before myself. I looked in the mirror one day and I didn’t even recognize who I was anymore. I had hit one of the lowest points in my life — physically, emotionally, psychologically — and something had to change.

I knew there had to be a group of people out there that shared the same values around autonomy and remote work as I did, and through extensive research, I found a fully remote SaaS company challenging the status quo of work waaay before anyone else was. I became their first Head of Employee Experience and discovered the unbelievable world of building a better workplace without any physical offices whatsoever. That’s really when I realized that I could take care of myself and live in an environment essential to my health and have my dream career — I wasn’t crazy! It did exist! The possibilities were endless! I watched 200+ people go through a very similar journey to work “freedom” as I did, and I defined my life’s purpose: work doesn’t have to suck.

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?

You may have heard “The Great Resignation” used synonymously with “The Great Reshuffle.” The latter is a phrase I identify the future of work with often. People don’t not want to work, they just want to work in environments that support their autonomy and belonging — that are built for meaning and purpose.

I think in general, we are going to work less as a society, and achieve more. While technology will continue to advance and AI will take over many menial tasks, it will free individuals up to truly work in their zone of genius to make an impact.

We’ll see the investment in global digital nomad communities continue to rise, and 30+ day working “vacations” will become the norm for many individuals and families. In tandem with this, governments will need to develop broader and more flexible tax strategies for a mobile workforce. Work will become more human and we’ll realize how similar we all really are based on our values.

I hope we’ll see a deep societal change in equalizing pay for women and underrepresented minorities. Companies will realize that there is an opportunity to invest in high-value technical skill training for lower socioeconomic classes, and build their teams based on diversity of thought to achieve greater innovation and create an incredibly diverse digital global workforce.

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

If you don’t have a robust People Experience team inclusive of organizational psychologists (or at least access to significant research) and a fleet of experience designers, start building that out…Now. In the meantime, look to anthropologists, sociologists, and global culture development to understand what type of culture you have, and understand your company’s DNA, and write. it. down.

Don’t wait to make a decision on your operating model. Hopefully by now, many employers have realized that the repetition of, “We’ll go back to the office in three months…Now it’s six…Maybe nine,” is getting old. Don’t forget about the employees who have now moved away, the remote ones you’ve hired without thinking it through, etc. Decide if you want to be fully remote, or go hybrid (be really really intentional here) then begin to build the blueprint of how you want your company to operate in the next three, five, ten years. Don’t wait another minute! I know it can feel overwhelming, but there are a myriad of resources and people (👋) out there to help you. This is truly the greatest innovation opportunity many companies will ever have — take it and enjoy it!

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?

Companies that choose to elevate one stakeholder over another will suffer. I think that a lot of companies are still looking at remote work to save them money and have a profit-first mindset. While profits are obviously essential when running a successful business, often the people behind the profits are easily forgotten.

We’re seeing countless corporations cancel office leases, save money on global travel, equipment, additional facility rental etc. Where are those savings going? I would encourage employers to think about these savings as a reinvestment in their actual workforce. There is an unbelievable opportunity for previously co-located companies to get creative with their budgets in the redesign of their working experience. Employers should be asking themselves, “What if we re-invested every saved dollar back into the development of our employees — from top-tier global benefits programs to robust learning and development curriculums? How much longer would our employees stay? How much better could they be at their jobs? How many more customers could we gain (and keep) with an energized and cared for workforce?”

I also think many employers just expect that someone with the right skillset is the right fit for their company and many employees are of the same mindset. There is an opportunity right now for employers to define their values, codify how they work as a company and design specifically to attract people who share the same values and operate in a similar way. Employees have work to do here as well, ensuring that they know their values, how they work best so we can create scalable win-win situations for the employer-employee relationship.

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

In a lot of ways, I think that working from home really hurt a lot of people and tainted their perspective on what the future of work can be.

We’re already seeing it influence the future of work in negative ways — specifically for companies that had very little digital infrastructure in place. The majority of people who have had a poor experience working from home, or those who have simply just replicated the office’s nine-to-five cadence are more likely to want to return to the office.

Until the majority of employers realize that remote doesn’t kill culture, it reveals it, we’ll continue to see a consistent rub with the willingness to shift mindsets and resources into the investment of the future of work. That said, many employers have seen the benefits of no commute time, as well as more time spent with family, friends, and in communities; and many leaders’ lives have personally been changed by the shift. The leaders who have been able to embrace the opportunity of working from home are the ones most likely to shepherd their organizations into the future.

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?

It will be necessary for society to accept ”non-traditional” lifestyles. For years, no one would take me seriously because I worked from the beach and lived in a camper van, even though I had a thriving career. Where people work has nothing to do with what they are able to achieve and the impact they can have, and I think it will take a while for that stigma to go away. Business suits have nothing to do with professional results — as a society we will need to integrate significant unconscious bias awareness in our organizations and communities.

Many parents are home, and at least (right now), many children are too with the rise of different COVID-19 variants. We’ll need to see investments, improvements, and changes in making affordable childcare accessible to all.

This sounds really simple, but people will need to learn how to be nicer to one another. In order to succeed in the future of work, we’ll need to lean on values of kindness, respect, accountability, equality, and integrity to build better.

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

THERE IS LITERALLY NO BETTER TIME TO WRITE OUR OWN STORY! What an opportunity we have in front of us to redesign a better world of work. I am absolutely filled to the top with excitement about what the future of work means for companies, people, and our environment.

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?

While we’re all in the same storm of life, most people are in very different lifeboats. Understanding that everyone is on a unique journey and has different mental health needs is essential to the design of employee benefit programs. The more autonomy that you can bake into your programs, the better. Normalize mental health days as sick days, hold community conversations when they are needed, and create safe spaces for mindfulness and wellness within your work ecosystem.

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?

Is your company operating in alignment with your values? Many people leave companies because they’ve discovered that the values they came for only truly ever lived on glass plaques on the office walls. Employers should take this very seriously. Leaders should be auditing their mission, vision, and values, and ensuring their operating model is designed around these three pillars — that individuals can feel the DNA in the majority of their interactions with written material and in conversations. Company cultures will need to evolve to hold themselves accountable for the culture they’ve created and adjust often when needed.

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

  1. Remote-first.
  • While many companies will choose a hybrid model, it will become clear very quickly that a hybrid model will be most successful when designed remote-first. Watch out for programs, policies, and behaviors to move (slowly) to a remote-first model. If the majority of a hybrid company’s employee-base is in office, this will be tough and companies will need to be very intentional about a remote-first design to mitigate location bias.

2. Diversity, equity, inclusion, and belonging as a core business focus.

  • Often, DEIB lies solely within the HR/People Ops department which is a significant disservice to the company ecosystem and the people they employ. I think we’ll see a trend of CEOs and leaders understanding the massive significance and impact in baking DEIB initiatives into company cultures and ensuring it is a part of the work experience vs. an add on.

3. Employee journey mapping.

  • Some companies are already doing this, but just as most customer-focused companies map their customer journey, all companies should be mirroring it with the employee journey. We’ll see investment in employee experience design, employee archetype research, and a hyper-focus on building a workplace framework that allows for both autonomy and connection.

4. From “off”site to “on”site.

  • I predict that we will see a significant rise in platforms and transformations in the hospitality industry to accommodate much more frequent corporate gatherings. Watch out for event experience design to become a substantial market in the next few decades.

5. The integration of work/life harmony.

  • We talk a lot about work/life balance and many have found that to be nearly impossible over the past two years. I think we’ll see a huge shift to work being a part of life and life being a part of work as many people during this “reshuffle” time begin to match with roles and companies aligned with their values. Don’t mistake this for overworking, but a more societal change into accepting that life is a part of work and work is a part of life (for some).

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?

“You don’t have to set yourself on fire to keep everybody else warm.” I’m honestly unsure who first said this, but thanks! It’s posted all over my office wall. As a recovering people pleaser, this quote always helps bring me back to myself and fill my own cup, so I’m able to be fully and wholly available for others without losing myself in the process.

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.

Patty McCord! I’ve highly admired her work over the years and she has been a significant mentor to me via her books, talks, and general public content. I would love to connect with her.

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?

Feel free to connect with me on LinkedIn.

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

Thanks, it’s been a pleasure.

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