Over my 15+ years in the field of dating coaching, I’ve seen dramatic shifts in the culture of dating that, interestingly enough, correlate with the rise in singlehood. Starting with free dating apps that made the online dating experience mobile and accessible to individuals with a variety of “relationship goals,” the speed of dating increased. And with it, the dissatisfaction of dating reached an all-time-high. Plus, decision paralysis set in as singles swiped through seemingly endless possibilities, leaving many unable or unwilling to select a partner at all.
The pandemic saw some singles “swiping” who’d never considered dating apps before, and while the most popular apps reported double-digit growth in the last year, the rate of relationships didn’t seem to increase accordingly. One could see this as an unmet desire to couple up, but qualitatively, I see that singles used this period to explore their options, and many concluded that singlehood was the right choice for them, business owners included.
One thing we can’t blame on the pandemic is a decrease in marriage rates. They’ve been steadily declining for some time, and recently hit their lowest level since the U.S. government began keeping national marriage records in 1867.
Among those previously partnered, divorce rates have been on the decline. Fewer young people are getting married or are delaying marriage, leaving many people in their 20s, 30s and 40s unpartnered. However, in the 50+ age demographic, the divorce rate has steadily grown over the last few decades and more Americans in that age group are falling into what the AARP (American Association of Retired Persons) labelled as the “gray divorce” trend.
The big question is why? What is driving people away from partnership? I believe that both finances and career flexibility play a huge part in it. This report examines intriguing new data collected from nearly 1,000 self-employed singles that give us a window into the pros and cons of partnership, its effect on self-employment and the attitudes that are driving folks away from the altar.
Despite the growing number of singles living here, life in the U.S. still caters to the “traditional” family unit—and if you don’t have someone to share your life (and expenses) with, it can make many life decisions and disruptions more challenging. Coupled-up folks often get the benefit of dual incomes, tax incentives that favor marriage and the relief of shared expenses. Singles report having more freedom in their life choices but often feel burdened by rising costs on everything from gas to groceries and the emotional toll of pursuing their dreams without a partner.
Examining responses from the 76% of participants in our study who identify as self-employed and the 23% who own a small business, we’ve outlined the benefits, drawbacks and hidden concerns of being single and self-employed in America.
Self-employed singles struggle with financial stability. Being single and self-employed can be a major financial challenge.
Financial instability keeps many self-employed singles from pursuing relationships—particularly if they’re on the younger side. One of the most cited obstacles to self-employment listed in the FreshBooks 2021 Self Employment Report are cash flow and inconsistent income.
Limited free time and strange work schedules contribute to self- employed singles’ relationship status. Running a business takes time—and for many self-employed singles, that means there’s no time to pursue a relationship.
Despite the challenges, many self-employed singles actually think it’s easier to run a business as a single person.
Most self-employed singles are single by choice—and despite the challenges, prefer it that way.
At First Glance: Does Being a Self-employed Single Make Some Things Easier?
Let’s jump right into the big picture. Does being self-employed and single make things easier or harder?
And the answer is—it depends.
It Depends on Dependents
Whether the dual-title of single and self-employed makes things easier or harder for a person will depend, in large part, on whether they have dependents. Taking care of a dependent (like a child or aging parent), can, of course, be an incredibly rewarding and enriching experience—but if you’re self-employed and single, it can also make things significantly more complicated. Taking care of other people requires time, energy and attention—and when you’re single and self-employed, that’s time, energy and attention that you don’t have to put towards building and growing your business.
There’s also the financial aspect. In today’s economy, taking care of a single person is expensive enough—and the more people you have to take care of, the more expensive it becomes, which can compound both financial strain and stress.
The good news? The large majority of self-employed singles in the U.S.—74%, to be exact—are not currently acting as the primary caregiver for any dependents (child or adult).
The bad news? A disproportionate number of single, self-employed people in the U.S. that are taking care of dependents are women. Self-employed single women in the U.S. are twice as likely as men to be the primary caregiver for a child or adult (35% for women vs. 17% for men)—and when you consider the gender pay gap (according to data from the Pew Research Center, women in the U.S. earn, on average, 84% of what men earn for similar work), taking care of a dependent becomes an even bigger financial burden.
“I Don’t Need To Ask Permission”
The question “is being single and self-employed a benefit or a drawback in the U.S. today?” isn’t strictly a financial one. There are a number of reasons why a single person may decide to branch out on their own and try their luck at starting a business—including the freedom and flexibility being single and self-employed offers.
When you’re self-employed, you’re the boss. You get to make the decisions and decide everything from your schedule and areas of focus to how much (or how little) you want to work on any given day. And when you’re single, there’s no one that you have to answer or cater to other than yourself. There’s no partner to question your decisions, your business structure or your work schedule, cadence or output.
So, if you’ve got a lot of client work on your schedule—and you want to work through the weekend to get a head start on your week? There’s no one there to tell you not to—and no one else’s plans or schedule you need to consider before making a decision. Or, on the flip side, if you decide you’re feeling burned out and want to take a few weeks off? Again, that’s your decision (and your decision alone) to make.
That flexibility is a major draw for many single, self-employed people.
According to the results of our survey, self-employed single people overwhelmingly appreciate the freedom, flexibility and independence that both their employment status and their marital status offers.
Self-employed singles also love the flexibility in how, when and where they work—and that scheduling flexibility is even more important for people that have major responsibilities outside of their businesses. For example, while 65% of all self-employed singles said they love having flexibility in their work schedule, 72% of pet owners cited scheduling flexibility as the main benefit of being self-employed and single—and self-employed singles over the age of 35 (an age where people typically start to have more financial and personal responsibilities, like a mortgage or a parent with health issues) were significantly more likely to value schedule flexibility than their under-35 counterparts.
Work-life Balance Is, Well, a Balance
Work-life balance can be tricky for self-employed people. Having freedom and flexibility in how, when and how much you work can certainly make for a better work-life balance—but when your income and livelihood relies on how, when and how much you work, it can be hard to step away from work and find a healthy balance with your personal life.
But what about if you’re single and self-employed? Does that make finding a healthy work-life balance easier—or even trickier?
Living the Dream: Single & Successful?
Sometimes, being single and self-employed is a matter of chance. But sometimes, people choose to be single while they’re pursuing their dreams of entrepreneurship—and those choices are driven by a few different factors, including:
Finances. The path to entrepreneurship can be a financially precarious one—and for many self-employed people, the lack of financial stability prevents them from pursuing a relationship. Twenty-eight percent of self-employed singles said they aren’t currently in a relationship because their financial situation is too uncertain. Men are more likely than women to cite financial uncertainty as a reason for not being in a relationship (35% vs. 20%)—and the older people get, the less likely they are to let financial uncertainty keep them from partnering up. (Thirty-four percent of self-employed singles 35 and under said their financial situation was too uncertain to be in a relationship—compared to 28% of self-employed singles between the ages of 36 and 55 and just 18% of self-employed singles age 55 and up.)
Time. Starting, growing and running a business takes time—and for many self-employed singles, that time requirement keeps them from pursuing a relationship. Twenty-two percent of single, self-employed people said they don’t have the time to devote to a relationship because of work—and 15% said their unusual work schedule makes relationships difficult.
Energy. Being self-employed doesn’t just require a lot of time; it also requires a lot of energy—energy self-employed singles don’t have to put towards finding or maintaining a relationship. Twenty-five percent of self-employed singles said they don’t have the attention to devote to a relationship because of work. Eleven percent said they’re too tired from work to be in a relationship—and 12% said they’re simply too stressed out by work to even think about partnering up.
In addition, some self-employed people actually think their success relies on their singlehood—19% of them, in fact. (Men are slightly more likely than women to think that their singlehood is directly correlated to their success—21% and 17%, respectively.) But even though some entrepreneurs are convinced their success is due to their single status, most self-employed singles—51%—don’t think their business success has anything to do with the fact that they’re single.
Bottom line? Being single and self-employed has both benefits and drawbacks—and whether the pros outweigh the cons varies based on people’s individual situations.
Self-employed Singles Face a Double Threat of Challenges
For example, married people get tax breaks. They get to share medical benefits, which can be a huge cost savings. They even save on things like phone plans and groceries (think “family plan” and “family size”).
This structure presents challenges to single people—and those challenges are compounded for single people who are also running a business.
The Financial Challenge: The Stable Salary
When you’re single and self-employed, you’re the only person bringing income into your household. That kind of financial instability, both from the general instability that comes from being an entrepreneur and the lack of a stable second income, presents one of the toughest challenges for self-employed singles.
Forty-six percent of self-employed singles cited not having a second income for financial stability as a major challenge (women, at 52%, were more likely to see this as a significant challenge than men, at 40%)—and 25% said not having another person to split expenses with (think rent/mortgage, bills and utilities) posed a challenge to their financial stability.
Not only does the lack of a stable second income make supporting yourself harder, but it also makes it more challenging to take risks in your business—whether that’s investing in a new product or service launch or taking a sabbatical when you’re feeling burned out and need some time off.
While they may not have a partner to share expenses, the good news is that many self-employed singles do have people they can rely on for financial support. Nearly half of self-employed singles (41%) said they turned to their family members for financial support. (The likelihood of self-employed singles relying on family for financial support definitely decreases as they age; while half of single, self-employed people 35 or under reported turning to family for financial help, that number was just 27% for self-employed singles over the age of 55.)
But not everyone can lean on family, friends, or outside resources for financial support. Thirty-one percent of self-employed single women said that, while they needed financial support, they didn’t have any source they could turn to—and 20% of self-employed single men reported the same.
That being said, there are plenty of self-employed singles who don’t want or need financial support from anyone but themselves. Twenty-four percent said they don’t need financial support—a number that increased over time, as people likely accumulated a stronger financial footing. (While just 15% of self-employed singles under the age of 35 said they didn’t worry about financial support at all, that number jumped to 42% for the over 55 crowd.)
But regardless of the financial challenges, most self-employed singles don’t think those challenges are necessarily tied to their single status. While 25% said they would be less financially stressed if they were in a committed relationship, a higher percentage—38%—disagreed with that sentiment. (That number is slightly higher for self-employed singles with dependents; 30% of self-employed singles caring for a child and 29% of self-employed singles caring for an adult said that being in a committed relationship would make them less financially stressed.)
Operational Challenge: The Second Set of Hands
Having financial support isn’t the only benefit a relationship can offer. Being in a committed partnership can offer operational and logistical support (free of charge!) that can be hard to come by when you’re single—support that can help as you’re building a business. For example, a partner might be more than willing to spend a Saturday helping to package and ship customer orders or respond to client inquiries if it helps to support their partner’s business.
So, the question is, do self-employed singles feel like they’re missing out on that support—and is it negatively impacting their businesses?
From the data, it seems that singles like being able to make business decisions without requiring the approval of others.
And while self-employed singles may not have the support of a partner, that doesn’t necessarily mean they don’t have any support at all. Although 48% of them work alone, nearly one-quarter of self-employed singles (24%) said they turn to friends and family to help with their businesses—and that number is higher for women versus men (27% vs. 22%) and for younger business owners versus older entrepreneurs (33% of self-employed business owners 35 and under-reported asking friends and family for help with their businesses—compared to just 23% for self-employed singles between the ages of 36 and 55 and 16% of self-employed singles 55 and up).
The Emotional Side
Clearly, there are financial and operational implications that go into running a business. But what about the emotional implications?
How are single business owners managing the emotional challenges of building, running and growing their businesses—without the emotional support that often comes with being in a committed partnership?
“Friends & Family Have My Back”
Younger self-employed entrepreneurs were the most likely to fill their emotional cup through their friends and family (50% for self-employed singles 35 and under, compared to 45% between the ages of 36 and 55 and 37% of single entrepreneurs 55 and older).
That number is drastically higher for self-employed singles raising kids; 50% of self-employed singles who identify as the primary caregiver for a child cited a lack of close emotional support as the main challenge of being single and self-employed.
Bro, Do You Even Need Emotional Support?
There are self-employed singles who get the emotional support they need from friends and family—and, on the contrary, there are self-employed singles who feel like they lack the emotional support they need.
But there are also self-employed singles who don’t think they need emotional support. And those self-employed singles are overwhelmingly men—and, more specifically, older men.
And these numbers were the highest in the older age demographic (20% of single male entrepreneurs aged 55 and up reported not needing any emotional support—compared to 13% for self-employed singles between the ages of 36 and 55 and 12% for the 35 and under set).
While every person has their own story, it’s not hard to see the correlation between being a man of a certain age and thinking that you don’t need emotional support to manage your business (and your life)—a correlation that likely stems from outdated cultural messaging and gender norms that say needing support is somehow emasculating (and that men should “man up” and deal with things on their own).
But what about pet owners who are also self-employed singles? Does being a pet parent provide the emotional support they need to navigate the worlds of singledom and self-employment?
The answer is complicated. Of the self-employed singles surveyed for this report, 25% have pets. And out of that 25%, 44% said that not having close enough emotional support was the biggest challenge of being a single entrepreneur—meaning nearly half of the self-employed single pet owners surveyed don’t think their pets provide the emotional support they need.
But 51% of self-employed single pet owners live alone and nearly half (49%) also said they’re not interested in a romantic relationship—which points to at least some of their emotional needs being met by their four-legged friends.
Sounds like some pets have a lot to deal with.
What Happens When No One Has Your Back?
Clearly, when it comes to sources of emotional support, it varies from person to person. Some self-employed singles rely on their families for emotional support. Others rely more heavily on their friends, while others turn to their cats, dogs and other pets.
And the rest? Well, some just don’t have anyone to turn to. Nearly half of all self-employed singles (46%) cited not having close emotional support as their biggest challenge in navigating single entrepreneurship—a number that’s pretty consistent for both men (40%) and women (48%).
According to the FreshBooks 2021 Entrepreneurship Report, access to benefits and healthcare is a blocker for many, particularly for older people. Among prospective entrepreneurs, 39% of those over the age of 55 expressed that access to benefits was a challenge versus 21% for people below the age of 55. This means that many entrepreneurs lack benefits for mental health services or benefits to help them keep their business running if they encounter an unexpected health event.
However, a 2021 FreshBooks Mental Health Report found that beyond turning to a partner for support, entrepreneurs turned to other small business owners, business advisors and life coaches with their mental health concerns.
So, the question is—how successful do self-employed singles feel?
Thirty-eight percent of self-employed singles reported the success of their business as on par with expectations. Some even take things a step further and are thriving—with 27% rating the success of their business as above expectations.
Sadly, there are also a lot of self-employed singles struggling, with 35% of them rating the success of their businesses below expectations.
So, Do Self-employed Singles Want To Couple Up?
After unpacking the experience of being single and self-employed from all these different angles, it’s clear that there are inherent challenges to being a single, self-employed professional in America.
But are these challenges worth it? If given the chance, would self-employed singles kiss the single life goodbye in favor of a committed, long-term partnership—and a solution to so many of the challenges they face?
Interestingly, for many self-employed singles, the answer to that question is a resounding NO.
By comparison, 33% of self-employed singles said they were either open to a relationship or would prefer to be in one—and, as such, are actively looking for a partner.
The reasons why self-employed singles prefer to stay that way vary; for example, 41% of self-employed singles believe that relationships are just harder when you’re a business owner. Nineteen percent said being self-employed makes it difficult—or even impossible—to be in a relationship. And after pouring everything they have into their businesses, they just don’t have the energy to put themselves out there and meet people.
And if you ask pet owners whether being a self-employed single gets in the way of finding a romantic partner, 28% will tell you they don't have the time to meet or date people. Apparently running a business and raising a puppy can really take it out of you!
However, while many self-employed singles think that their status as an entrepreneur keeps them from being in a healthy, loving, committed relationship, that belief tends to fade as they get older. While 29% of business owners under the age of 35 reported that being a self-employed single gets in the way of finding a romantic partner, that number dropped to just 15% for self-employed singles over the age of 55.
Still … the World Is Not Built for Self-Employed Singles
But a huge portion of those self-employed singles like being both single and self-employed—and aren’t interested in changing their personal or professional identity just to fit social norms.
From their perspective, they’re not the ones that need to change. It’s the world that needs to shift.
So, what, exactly, might that look like?
Financial support. Self-employed singles don’t have the benefit of a second household income—which can make the financial implications of both running their business and covering their personal expenses a serious challenge. Providing financial support to self-employed singles in the form of low interest business loans, access to capital and tax breaks could relieve some of their financial burden—making it easier to start, build and grow successful businesses without putting themselves in financial jeopardy.
Emotional support. Self-employed singles need access to emotional support systems including therapy and helping professionals. The lack of healthcare benefits for self-employed singles can mean that they see mental health services as a luxury rather than a foundational element to their long-term business success.
Small business associations. Self-employed singles need a place to connect with other small business owners—and small business associations can be a great way to find those opportunities to connect and network.
Community. In addition to more professional networks, self-employed singles also need access to communities (like FreshBooks!) of like-minded professionals where they can share ideas, get support or just be reminded that they’re not alone.
The right tools. Self-employed singles are generally managing their businesses (and their lives!) solo—and so the right automation tools (like invoicing software and calendar management tools) are essential in helping them optimize their time.
Access to data. We can’t take steps to solve the challenges facing self-employed singles if we don’t understand what those challenges are—which is why access to data on self-employed singles (like this report!) is essential.
The respect and recognition they deserve. Arguably the best thing society could do for self-employed singles is to stop treating singlehood as a curse—and instead, respect it as the choice, preference and legitimate status that it is.
How We Made This Study: Methodology
FreshBooks designed and executed research for this report in collaboration with Centiment. More than 1000 single people—who are either self-employed or own a small business—were surveyed online in April 2022. The study’s margin of error is +/- 3% at 95% confidence. The data collected here was used in collaboration with Damona Hoffman and FreshBooks to create this report.
About Damona Hoffman
Celebrity Dating Coach Damona Hoffman has been coaching singles on how to find love online and offline for over 15 years. Her articles appear regularly in The LA Times and The Washington Post. Plus, she’s a regular on-air contributor to The Drew Barrymore Show, NPR, and NBC’s Access Daily. Damona also starred in two A+E Networks’ TV shows: #BlackLove and A Question of Love. Her weekly podcast Dates & Mates has been featured in Cosmopolitan, Huff Post, Bustle and tops the charts in the Relationships category on the major podcast platforms.
FreshBooks is changing the way business owners manage their books. Its owner-first accounting platform, loved by businesses in over 160 countries, takes an easy-to-use approach to managing finances, billing, payments, and client engagement. FreshBooks, known for its 10x Stevie award winning customer support, serves customers of all sizes from offices in Canada, Croatia, Mexico, Germany, Netherlands, and the US.