What does success mean for the next wave of entrepreneurs?

Eloise Skinner’s plan was simple: Earn a place at the University of Cambridge to study law. Join a prestigious law firm. Then hustle, grind, and sweat her way to the top.

After eight years of study and work, she was making impressive headway. She was an associate at an international law firm. She was helping enormous multinationals navigate the treacherous worlds of tax and regulation. Praise was rife and rewards were common. By any traditional measure, Skinner was a runaway success. Unfortunately, that success left her feeling hollow.

“Those ideas of success never really lived up to expectations,” she said in an interview earlier this year. “It took a long time for me to realize that finding purpose in life is not necessarily simple, and it’s a totally unique journey for each one of us.”

During her final few years in corporate law, Skinner began nudging her career towards her personal interests. From a young age, she had always wanted to write a book. Not quite ready to give up the world of law, she resolved to write a handbook for junior lawyers. The changes and tweaks to her career path made success feel more rewarding and tangible—but it wasn’t enough.

With the success of her first book, another deal beckoned. The offer inspired Skinner to leave the rigid world of corporate law, and she drifted toward soloprensurship, starting two businesses: a purpose-led consultancy and an ed-tech startup. 

Her new work took on meaning and a higher sense of self-satisfaction, but it was also an important departure from traditional markers of success. Without formal promotion tracks, review processes, and recognition rituals, the young entrepreneur had to redefine what success meant for her and her business.

“There are no set standards for how fast things should progress,” she tells Dropbox. “It’s difficult to find a peer group to measure against.”

Since the pandemic, millions of people have struck out on their own, chasing passions, dreams, and ambitions. They’ve traded the prestige of the corner office for location freedom, employee of the month plaques for flexibility, and bonuses and cash for priceless family time. And like Skinner, they have had to reassess what achievement means, creating a mosaic of definitions as diverse as the founders themselves.

Success doesn’t mean what we think it does

It’s a biological fact: success feels good. Natural selection meant humans developed a mechanism that rewards us with serotonin when we succeed. When our ancestors fended off competing hunter-gatherers or brought down a tasty wooly mammoth, happy hormones flooded into their brains. This process isn’t just a one-off experience either. Every dose of serotonin reinforces the behavior cycle that caused its release.

“Each time serotonin or oxytocin is released, neurons connect that guide future expectations about how to stimulate it,” wrote Loretta Breuning Ph.D., founder of the Inner Mammal Institute, in Psychology Today. “We all wire ourselves to seek good feelings in ways that worked before.”

This mechanism still whirs in our brains today. Without a mammoth to chase or a saber tooth tiger to fend off, people have looked elsewhere. For decades, we’ve fed this biological mechanism with extrinsic markers of success: promotions, corner offices, and cars.

Like many young professionals, Skinner initially chased the sort of success society told her to: “a stable, well-paying career, owning a house, having a clear career path ahead of me.” It’s clear why. These traditional markers of success are firmly entrenched in our companies; they’re the default. They are the carrot dangled with job offers and the rewards stemming from positive yearly reviews.

But here’s the thing: most people don’t value traditional markers despite how large they loom in corporate culture.

Just 4% of workers said a corner office is a measure of professional success. Having a job respected by peers is only marginally more coveted at 14%. People see titles as less important than skill development. More than one-third said they would take a 10% pay-cut to design their own schedule. 

Even when Harvard Business Review exclusively polled high-powered executives, personal and subjective criteria dominated the discussion. Respondents said rewarding relationships were the main factor in personal success. Friends, family life, and balance were also important. “The 10 minutes I give my kids at night is one million times greater than spending that 10 minutes at work,” said one interviewee.

This disconnect between values and work is confusing. After all, if we value flexible schedules above promotions, why do we work backbreaking hours? One explanation may rest in how we have codified success in our culture.

“The idea that we must pursue success in order to experience happiness is enshrined in the United States’s most treasured institutions (the Declaration of Independence), beliefs (the American dream), and stories (Rocky and Cinderella),” wrote happiness researchers Lisa Walsh, Julia Boehm, and Sonja Lyubomirsky, in Aeon. Although the specifics of cultural values and corporate reality differ around the world, the schism appears constant.

We’re trapped in an environment that pushes nonsensical markers of success. Independent work provides an opportunity to scrap everything and start again.

Success means what?

Independent work shatters the mature, inflexible, and often inalterable professional environment into millions of unique environments. Just as people can determine their own founding principles, operations, and processes, so too can they set their own definition of success. 

Danielle Hu spent several years working in finance. She quantified success by the number of zeros on her paycheck and benchmarked her performance by comparing her promotion schedule to her colleagues. But none of that was truly important to her. What was important—and please no poor Scottish accents—was freedom.

“Financial freedom, time freedom, and location freedom,” she said. “The freedom to choose what I want to work on, when I want to work, where I want to work, and with whom I want to work.”

Hu left the world of finance in 2017, starting an online business coaching consultancy. The freedom that originally tempted her away from finance forms a core part of her coaching: Her mission is to enable travel and freedom through entrepreneurship.

“That [freedom] led to increased happiness, and an absolute feeling of fulfillment that was nowhere to be found at my corporate job,” she tells Dropbox.

Although Hu’s success criteria are radically different to those common in traditional businesses, her means of measurement need not be. John Doer, the organizational leader who popularized the Objectives and Key Results (OKRs) goal-setting methodology, commonly applied his theory to non-traditional objectives, too.

The methodology operates on a simple formula: I will (Objective) as measured by (Key Results). Usually, the objective is something like “Exceed Q4 quotes by 25%” or “Achieve fiscal sustainability.” Key results are the criteria by which you measure progress. “Generate 60 Sales Qualified Leads (SQLs) by end of Q1” would work for the former objective. “Reduce the general budget variance from 10% to 5%” would fit the latter.

OKRs may feel antisceptic and inhuman, like you’re boiling down something deeply personal to checkboxes and statistics—but stay with me.

In an interview on Recode Decode, Doerr revealed that he used OKRs to measure unusual parts of his life. He valued family time, he explained, so set one objective as: “Be home for dinner by 6:00 p.m. 20 nights a month and be present.” It proved the flexibility of OKRs. If you have a goal, it can fit the structure. Hu could easily set an objective for herself of “Ensure 60% of my time is free” or “Work in 10 different locations this year.”

Doerr was an OKR fanatic. He’s written books on the methodology and gives endless talks on the subject. Will distilling family time to a corporate-style goal work for you? Possibly, possibly not. But know that goal-setting methodologies can accomodate non-traditional success criteria. 

That flexibility is well-needed because independent workers have definitions of success as varied as they are.

Success is what you make it

Many measure their success against their business’s purpose or mission. Samantha Tollworthy is one of those people. She worked in TV production for the better part of a decade, most recently as a wildlife specialist traveling to some of the most remote places on earth. It was her dream job. But she gave it up to chase purpose and meaning.

She built her new venture, a sustainable sock business, from “the fiber up.” To Tollworthy, success doesn’t mean revenue or profit. Her positive impact is the only metric that matters: inspiring people to make sustainable switches, diverting waste from landfill, and offsetting carbon emissions.

“I changed career paths to make a difference,” she said. “Reminding myself of the sacrifices made to contribute to the fight against climate change is the biggest measure of success.”

For some, success means spending time with family. A late night in the office counts as a failure. Clocking off early to make it to parents’ night is a success. Autonomy is a key factor for many. If they can dictate their own destiny, rather than live under corporate rule, that’s enough. And some have chosen to retain the old markers of success: cash, cars, and prestige. That’s okay too, because when you’re your own boss, you set the rules.

Ultimately, success is something you must define for yourself, Dr. Elizabeth Lombardo, psychologist, author, and “Head Coach for Happiness” to NBA star Shaquille O'Neal, tells Dropbox. No one else can do it for you.

“Success could imply a sense of contributing to society and making a difference,” she said. “It could mean a sense of accomplishment and advancement in your career. It could imply being able to pursue your passions. It is the ability to achieve your life's objectives, whatever they may be. There is no one-size-fits-all approach to success.”

What of Eloise Skinner, the corporate law hotshot turned writer-entrepreneur?

She’s still running her two companies. Instead of houses, cars, and traditional career progression, she’s substituted a her own measure of success: purpose.

“I feel most successful when I'm spending my time in a meaningful way,” she says. “It's a bit of a subjective measurement, but it's really a case of checking in with myself to see if I'm finding purpose in the work I do.”