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3 Big Challenges To Imagining The Future Of Work


Back when I was in my 20s and about to step into the “real world,” there was no discussion about working remotely, or “wanting to be mentored.”

I’m 41 years old now, but back in the 90s, there was a completely different set of expectations about work. You got smacked around. You paid your dues. You worked hard and didn’t expect your employer to give you “life advice” or guidance as to how you could climb the ladder faster. That’s what college was for—at least, that’s what employers expected it to be.

But today’s workplace looks nothing like it did twenty or thirty years ago.

In some ways, the changes are obvious: working remotely, for example, being the product of today’s new digital landscape. In 2017, The New York Times reported that “43 percent of employed Americans spend at least some time working remotely.” Then, in 2018, CNBC reported that “70% of people globally work remotely at least once per week.” That’s a lot of people not showing up to an office (which, ten years ago, was a non-negotiable requirement).

But working remotely, for example, is just the tip of the iceberg.

The truth is, some of the biggest workplace shifts have much more to do with education and communication.

We now live in a world that’s determined by signals.

Where you went to school. Who you’re connected to on LinkedIn. How many followers you have on Instagram. All of these things communicate, at a glance (and at scale), who someone “is” and where they fit into the hierarchy in society.

Sometimes, we forget things didn’t use to be this way. Back in “the old days,” resumes couldn’t be crawled at scale using LinkedIn data and its ilk, and it was still possible for you to randomly connect with someone on a train—or interview with a company simply because they didn’t know any better. But that’s not how the working world operates anymore. Contrast that to today and, “Over 80 percent of employers and 90 percent of recruiters review social media profiles sometimes or all the time for insight on candidates,” according to a recruitment study by The Martec Group.

Yet, with all these new digital tools at our disposal, “63% of recruiters report an inability to find qualified candidates as their primary challenge.”

The reason is that the future of work is going to be dependent upon more than some simple qualification parameters.

With the rise of automation, we’ve now created a workforce built upon keywords.

When a recruiter is looking for a candidate, they’re plugging a few parameters into a technology tool or platform (college, degree, years of experience, previous title, etc.). They’re looking for the tool to “tell them” who they should be looking for, which inherently rules out any and all spontaneity. It fundamentally removes the option for a candidate that may not have any of those relevant “keywords” in their background, but culturally might be the perfect fit for your organization. That’s the world we live in today—and even though we’ve removed a lot of areas with friction with these digital tools, the entire process of “discovering meaningful connections” is still largely broken.

These are the problems I find myself thinking through with my team at Olmo, as we imagine what a world of meaningful connections looks like in the digital age.

Here are the 3 big challenges we feel must be overcome in order to reimagine the future of work:

1. Success begets success, which means someone who is just starting out struggles to get ahead.

“The rich get richer” is a cliche because, well, it’s true.

In modern day society, previous success has a disproportionate impact on future success, meaning that if you have proven yourself once it’s even easier to earn a second “at bat” (and so on, and so forth). For anyone who hasn’t yet experienced some level of success, this is a huge hurdle to overcome.

There are usually two big hurdles that keep people from being able to “level up” professionally.

The first is getting your foot in the door in the first place. Young people often struggle to get the jobs they truly want because most companies don’t want to inherit the risk of “training someone new.” Instead, they require 2+ years of experience, even for most entry-level positions. But how is a recent college graduate or someone who just finished a Master’s program supposed to have two years of experience?

The second is, most people experience traction in their careers before they even know whether they’re doing something they enjoy in the first place. They graduate. They take a job. They get a promotion or two. And then by the time they realize how “the game” works, they’re too far gone. They would need to start completely over if they wanted to do something different, and the risks that come with that cause most people to accept their path in life and continue forward.

So, how do you solve both of these issues?


Many of the most valuable skills in life and in business are soft skills: communication, relationship management, leadership, etc. Which means, if the system is not currently designed to help people maneuver and take control of their careers, then the only other way to advance and overcome some of these hurdles is to make meaningful connections with people with influence. We already know networking is the reason some people get terrific jobs right out of college and others don’t. We’re already aware of the power behind the cliche business phrase, “It’s all about who you know.”

This is problem number one we’re thinking about as we design Olmo.

2. Companies are becoming more and more focused on short-term hires, which means employees need to be focused on acquiring transferable skills.

Today’s job market is sending a very clear message to today’s younger generations:

The roles people are hiring for today, won’t be the roles they’re hiring for tomorrow.

In 2016, Pew Research Center published a fascinating report on the state of American jobs. And while it’s full of incredibly impactful takeaways, one of the most obvious is our workforce’s desire to continue their own personal growth. According to the report, “More than half (54%) of adults in the labor force say it will be essential for them to get training and develop new skills throughout their work life in order to keep up with changes in the workplace.” That’s a significant amount of people who are aware that what they’ve been hired to do today might not be all that necessary in the future.

On top of that, “35% of workers, including about 27% of adults with at least a bachelor’s degree, say they don’t have the education and training they need to get ahead at work. 45% of employed adults say they got extra training to improve their job skills in the past 12 months.”

So, what does this data tell us?

A recent Wall Street Journal article put it eloquently: “Instead of teaching new skills to their current workers, employers often choose the disruption and high costs of layoffs or buyouts.” Which means, regardless of whether you’re an entry-level employee, a middle manager looking to make a career change, or a seasoned VP trying to become a leading executive, it’s not going to be the company that gives you the skills required to move up the ladder. It’s going to be you—and in your own time.

All of this to say, as more and more companies look to automate tasks, and shortcut internal training, it’s going to be the human social skills that become the real business advantages. Skills like being able to seek out and learn from someone who already possesses the skill you’re looking to acquire. Being able to display value through a meaningful conversation. Being able to pick up on subtle social cues, and understand people’s pain points without needing them to be pointed out in the first place.

As the future of work solidifies itself as digital, it’s going to be the fundamental human skills that remain most relevant.

3. In the increasingly distracted and isolated digital age, people who understand how to form meaningful connections will have the advantage.

Consuming social media is far from social activity.

The truth is, many people consume social media by themselves. They feel as though they’re “logged in” to a big party when in reality, they’re sitting on the couch at home by themselves. It’s a deceiving experience and one that creates the illusion that we’re meeting people and connecting with (or “following”) each other.

But talk to anyone who has built an incredibly powerful network, and chances are, they see social media as white noise.

Because the most meaningful connections in life come through genuine conversation. They happen over dinner, or a night out trading stories. They happen through an introduction from a close friend or a close co-worker. They are nurtured over time, and they usually turn into some sort of friendship, and in the end, that’s why they’re so valuable. Both parties have invested time and energy into building it.

As the world continues in this direction of social media, it’s going to be the closed or vetted social networks that add the most value to people’s lives (which is actually the core reason why we’re launching Olmo as an invite-only platform). But more than that, it’s going to be the individuals who invest in bringing these online connections, offline, that possess the greatest professional advantage.

People want to help people they know and have formed some sort of bond with. Plain and simple.

I'm a repeat entrepreneur currently focused on Olmo, a mobile app that makes warm professional introductions so people can make better decisions and enjoy greater access to opportunities. We're currently in private beta and will launch in the coming months. The app looks awesome and we're making great connections every day. Sign up on to request early access.

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