“I Have Nothing”: Millennials Are Starting To Have Their Midlife Crisis

A 36-year-old content creator who said he had moved back in with his parents after a second failed business has become a striking example of the kind of financial and personal crisis that many millennials are beginning to confront as they move deeper into adulthood.

Lifestyle and motivation YouTuber Dapper Dev recently reacted to an Instagram reel from creator Ian Wilson, who said he had no money, no wife, no children and no clear path toward the life he thought he would have by his mid-30s.

Wilson described the situation as humiliating, but said he was sharing it because social media rarely shows what business failure actually feels like when the motivational slogans and success stories fall away.

“I’m 36 years old and I just moved back in with my parents because my business just failed,” Wilson said. “It’s my second business to fail in the last 10 years.”

Wilson Says Starting Over Feels Lonely And Endless

Wilson said he had poured himself into trying to build businesses, only to find himself starting over again at an age when many people expect to be financially established.

“I don’t have any money. I don’t have a wife. I don’t have kids,” he said. “And I’m not close to doing any of those things.”

He also said that starting a business was far more difficult than the image often presented online, where creators are more likely to show revenue screenshots, new purchases and success stories than the long stretches of fear and uncertainty that can come before them.

Wilson described the experience as “lonely and scary and endless,” although he made clear that he was not giving up.

Dev said that part of the video stood out because Wilson had clearly given years of his life to trying to build something, and now found himself in a position where he had to return home and rethink almost everything.

There is something especially difficult about reaching your mid-30s and realizing that the milestones you assumed would arrive naturally may not arrive on schedule at all. That gap between expectation and reality is often where a midlife crisis begins, even if it looks very different from the stereotypical version involving sports cars and impulsive spending.

Moving Back Home May Become More Common

Dev said he believes more adults are going to have to consider living with parents, relatives or roommates for much longer than they expected, not because they necessarily want to, but because housing and everyday expenses leave fewer realistic alternatives.

He said people may need to “band together” with family members and reduce their monthly costs aggressively while also looking for new ways to increase income.

Dev acknowledged that nobody has to enjoy that arrangement, and he was not suggesting that people lose the right to complain about it.

His point was that the old expectation of leaving home once, living independently forever and steadily becoming more financially secure may no longer match the reality many adults are facing.

He argued that people are going to have to become far more creative about spending less and making more, which could include multigenerational living, roommates later in life or combining several income streams.

That may sound like a step backward to people who grew up being told that independence was the marker of adulthood, but in some cases it may simply be the financially sensible choice.

Dev Says Trust In The Traditional Career Is Fading

Another part of Dev’s response focused on how much confidence people have lost in the traditional 9-to-5 career path.

He said many workers no longer believe that giving decades to one employer will necessarily result in stability or a comfortable retirement.

To illustrate the point, Dev told a story about a man he knew in the roofing supply business who had worked for the same company for years and was well liked by employees and contractors.

According to Dev, the man was fired about a week before retirement over what Dev described as a ridiculous reason.

He said seeing stories like that makes it difficult to trust the idea that loyalty to a company will always be rewarded.

Dev still believes having a steady job is valuable, but he argued that for many people, a 40-hour workweek may no longer generate enough income to comfortably cover expenses and build long-term security.

His answer was not especially comforting: he thinks more people will need side businesses, second jobs or other sources of income.

YouTube Is Not The Easy Side Hustle People Imagine

Wilson’s failed-business story also led Dev into a discussion about YouTube, which many people view as a possible escape from traditional employment.

Dev said he has been making videos for years and has managed to build an audience and monetize his channel, but warned that the process is much harder than outsiders often assume.

He said creators have to consistently produce videos, study titles and thumbnails, deal with technical mistakes, interact with viewers and somehow generate enough traffic to make the work financially worthwhile.

In Dev’s experience, advertising revenue alone is rarely enough for smaller creators to justify the time required.

He said anyone entering YouTube solely because they think it will be easy money is likely to burn out.

Instead, Dev suggested that creators who genuinely enjoy making content should think more broadly about building direct relationships with their audiences, including support through platforms such as Patreon, Buy Me a Coffee or similar services.

He said his own thinking about YouTube has changed as he has spent more time on the platform and become less confident that advertising revenue will remain predictable.

The Side Hustle Can Fail Too

That part of Dev’s discussion adds an important complication to the common advice that struggling workers should simply start something on the side.

Wilson’s story is already an example of how difficult entrepreneurship can be, while Dev’s experience shows that even an accessible-looking business like YouTube can require enormous effort without guaranteeing much income.

Dev said money ultimately matters because there comes a point where a project that consumes large amounts of time may simply no longer make sense if the financial return never materializes.

He also expressed concern about relying too heavily on large platforms or employers, saying he has seen creators lose channels or videos and believes algorithmic moderation can sometimes make unpredictable decisions.

Whether someone is working for a corporation or building an audience online, Dev’s larger concern is the same: depending entirely on one institution can leave a person vulnerable when the rules change.

‘We’re Going To Have To Get Used To Living Different’

Toward the end of the video, Dev broadened the discussion beyond Wilson and argued that American ideas about independence, consumption and lifestyle may have to change.

He contrasted what he sees as strong family cooperation in many immigrant and non-Western households with the American emphasis on individual privacy and maintaining separate households.

Dev said people often want their own space, constant upgrades and the appearance of progress, while social media and consumer culture reinforce the expectation that each stage of life should come with something bigger or better.

He believes that model is becoming harder to sustain.

Instead, he said people may have to cut spending enough that the changes are noticeable in daily life, while also accepting that earning more could require working beyond a standard 40-hour week.

It is not an especially cheerful message, but Wilson’s reel gives the argument a human face.

At 36, Wilson is not presenting himself as someone who has given up; he is presenting himself as someone who followed an ambitious path, failed twice and now has to rebuild without pretending the experience is glamorous.

That may be why the video resonates.

For millennials entering their late 30s and 40s, the crisis may not be about having everything and wondering whether it was worth it, but about reaching the middle of adulthood and realizing that many of the things they expected to have are still out of reach.