Dispatch - Q3 2022

It used to be that you’d spend your whole career at one or a small handful of companies who’d invest in you over time because they could be confident you’d stick around. But those days are long gone. Many millennials haven’t spent more than a few years with a particular employer, instead hopping from job to job and gig to gig, sometimes by choice, sometimes by necessity. 

This position is seen by some among the elder generation as a position of precarity. But we at Gather believe that with strategic planning, independent knowledge work can make for a more secure and stable career. 

To learn more about how we should be thinking about our careers, we spoke with Gather Founder and President Justin Tobin. 

“You diversify the portfolio of money you own,” Justin says. “Why not diversify the portfolio of money you’re earning?” By building and maintaining a list of client relationships, you can be choosier about the kind of work you take. And because you can spread multiple workstreams across your week, you always have something in the hopper, even if a big client relationship falls through. 

When you unexpectedly lose a full-time job, on the other hand, it’s like losing a lifeline. Your income goes to zero, and you lose various benefits that are critical to you and possibly your family’s livelihood. How many times have you heard someone say, “I hate this job, but I have to stay, because if I leave I’ll lose my health insurance / maternity leave / unused paid time off”? 

Lining up another full-time job is itself a full-time job that can take months. The fear of facing months of unemployment and the tarnishing effect such gaps can have on a CV tends to tie workers to less-than-ideal jobs longer than they’d like. With independent work, on the other hand, you’ve always got other irons in the fire. You’ve probably got some secondary workstream cooking that can help you meet your basic needs if a main gig ends abruptly. Maybe you can ramp up hours on a back-burner project. Maybe you can hit up a contact for a quick one-and-done gig to get you over the gap to something more substantial. Or maybe you can simply take a short break. You’ve got options, because you’ve built a wide network of clients and colleagues who can trust you as their turnkey solution. 

David Gaspar’s, Gather’s Head of Innovation, 32-hour work week concept is critical here. This principle applies the 80/20 rule, encouraging workers to spend around 20% (or one day a week) of their working time devoted to business development. It can be tempting, when one has locked in a great gig, to want to go “full throttle” on it in order to maximize present income. And in some cases, that’s fine. The 32-hour work week concept, in contrast, has workers thinking about future income as well, so if that fat account disappears, you have something to fall back on. 

There is a commonly assumed calculus of independent work, wherein that security and stability are indirectly proportional to freedom and flexibility. Meaning, independent workers generally enjoy lots of the latter, and little of the former, and that full timers enjoy lots of the former and little of the latter. 

Let’s dispose of this myth once and for all.

“In terms of full time employment offering more security, it has to be said that that ‘security’ is complete and utter bullshit,” said Tobin, in the most recent episode of the Gather Dispatch podcast. “And I think that even the most loyal employees of any Fortune 500 company would ultimately, after two or three drinks, probably recognize that. They all know that employment is an at-will deal.” 

The sad truth is that firms exist to make money, and if their relationship with you isn’t making money (even if through no fault of yours), they will generally terminate your employment the moment it becomes expedient for them to do so. It doesn’t matter how many years you’ve been there. It doesn’t matter how many late nights you’ve pulled for the company. It doesn’t matter how much human resources tries to convince you that you’re part of a family. Firms must ruthlessly cut costs in order to stay competitive. It might have nothing to do with you or your performance. That’s just life under capitalism, and there is usually no familial loyalty in that context. This sense of security and stability that people still associate with full time employment is a false one, one that is based on economic conditions that no longer exist. 

Workers are slowly waking up to this reality, and they’re also recognizing that independent work doesn’t mean a life of precarity.

Another problem with being a “lifer” at a particular firm is that companies tend to train their employees to be better functioning cogs within their particular work ecosystem. If you spend several decades working as a manager at Acme corporation, your skill set will obviously advance and improve during that time. But a large portion of those skills might not be transferable to other firms. Those are Acme skills. Senior employees who are laid off late in their careers often find that they had become very good at navigating the organizational folkways of their firm, and that much of their effectiveness in their career came down to knowing who had power within the organization, how to navigate the bureaucracy, and how to approach the peculiarities of the firms office politics. These are valuable skills if you want to keep working for that particular firm forever. But becoming ‘institutionalized’ doesn’t necessarily translate to success outside of Acme.

With this buildup of nontransferable skills, people rightly recognize that they’ll have a difficult time finding a similar job somewhere else. So the longer they stay with a particular firm, the more they feel like they can never leave without having to take a pay cut or start from some sort of lower rank.

“I have had former colleagues who were at companies for literally decades that have confided in me that they know that they can’t — whether they want to go somewhere else or be independent or just be in the marketplace — terrified because they know that they’ve been institutionalized,” says Tobin. “These are SVP, EVP, C-level executives. Hearing that coming out of their mouths, albeit in confidence, is really eye opening.”

“It’s heartbreaking to me when you get layoffs,” says Ben Edwards, Managing Director, Organizational Performance at Gather. “Departments get torn down and thrown out the back door, and people are like, ‘Well, what are my skills?’ And the answer is that the company has not taken care of that for them.”

When you suddenly lose a job, especially at a high experience level, you may find that your skills are so particular to your previous job that you have difficulty attracting recruiters. As Tobin puts it, “You’ve spent your life training for the 100-yard dash, and the 100-yard dash just fired you. Now you need to be a decathlete.” 

As an independent knowledge worker, you’re training to be a decathlete from the start. You develop an ability to make yourself useful within a variety of organizational contexts. You get a knack for plugging in wherever you’re needed, quickly intuiting how you can address immediate needs and add value. It’s a tremendously valuable skill to have right now, but it can only be developed by doing. Decathlon training takes time.In the last Dispatch, we discussed how important it is to cultivate community as an independent worker. It’s worth repeating this wisdom within the context of career-building too. Decathletes don’t train alone, they’ve got coaches and teammates making up their support network. Your support network follows you throughout your career, and becomes more valuable over time.

One of the most difficult stages for workers, both independent and not, to navigate is retirement. It’s a decision that involves many variables, and once you take it, it’s very hard to undo. Retiring from a career as a full time employee is a bit like turning a light switch from the “on” position to “off.” You have a job, and then you don’t. 

After more than three decades of overseeing events full time for Major League Baseball, among other career highlights, new Gather member Marla Miller realized that it was time to make a change. But she didn’t necessarily want to go from riding a moving train to a rocking chair on the front porch. 

“I’ve always worked,” Miller says. “I love my work. And whether it’s something big or something small, I always felt I had a lot to contribute.”

Over the last five years, she began asking herself what her next step could be. The culmination of these deliberations was MEMG, a live sports and entertainment consulting firm. Miller runs this firm alongside longtime colleagues. It enabled her to move away from her employer through a more gradual transition. Now she has much more freedom and flexibility in her work, and more security in deciding the terms of her eventual retirement. Instead of treating the close of her career like a traditional light switch, Miller’s operates more like a dimmer switch that can be dialed down (or back up) gradually as needed, giving her more security and stability than she might’ve had if she were leaving her longtime employer and going straight into full retirement. 

It also puts her in control of the switch. A lot of folks unfortunately find late in their careers that their employer is less loyal to them than they are to it. These folks can be tragically laid off a few years before they’d planned to retire. What do you do when you’re laid off at 62, and you thought you had a few more years to save up? You might not be able to just retire early, and getting a new job at a similar compensation level, at your experience level, is easier said than done. The independent work model can give you more control over when and how you retire, and prevent a situation where you’re forced to retire at an inopportune time, due to factors outside your control. 

This of course applies not just to retirement, but any kind of big life change. Maybe you’re moving from New York to California and want to experience the country via a prolonged road trip. You imagine snatching a few hours here and there to catch up on work. An independent worker could figure out a way to make this work, but a full timer would most likely have to call this a vacation and forget about getting any work done (Ed note: I did this a few years ago and it was great). Maybe you’re in the last few months of pregnancy and you don’t necessarily want to fully transition into “parental leave” mode, but you don’t want to work 40 hours a week either, because you’re exhausted and sore all the time. With independent work, you can make finer adjustments on that dimmer switch. 

Across life’s many twists and turns, there are going to be moments when you want to work some, but not all of the time. Full time arrangements are not built for this kind of nuance. But when you’re an independent, the when, how, and where of work are under your control. Freedom and flexibility and security and stability. There’s no tradeoff, it’s all gravy. 

That’s another Dispatch, in the bag! Thanks for joining us as we explore the present and future of independent knowledge work. Next month we’re going to discuss how independents can navigate the tricky waters of a recession. We think there are reasons to be optimistic, and we hope you’ll stay tuned. Speaking of tuned, did you know that the Dispatch now has a podcast component? That’s right, Gather’s Jason Oberholtzer and co-host Mimi Sun Longo are hosting roundtable discussions with folks across the Gather Network that are meant to accompany these newsletters. Think of this podcast as a livelier, more personal accompaniment to what you read here. It’s like a bar meetup after a talk, where you and your smartest pals meet up to dish on what was discussed.

A roundtable of Gatherers with decades of experience in leadership and mentoring roles, inside and outside of large corporations, reflects on career security, stability and fulfillment, and on how independent work factors into the landscape of possibilities for workers across the stages of their work life, from early opportunities through retirement and beyond.