By the time people reach their mid-30s, many begin confronting a quieter kind of disappointment that is rarely discussed openly: the realization that life may not look anything like the version they imagined when they were younger.
Commentary YouTuber Jack Morgan explored that feeling in a recent episode of the Red Leather Podcast after reacting to a TikTok by mental health advocate Romellus Wilson, who described the years between roughly 33 and 40 as a period when people often begin grieving the life they expected to have.
Morgan, who is 36, said much of Wilson’s description felt familiar, even though parts of his own life eventually did turn out close to what he had hoped for. The deeper point, both men suggested, is that adulthood rarely follows the clean sequence people imagine in their teens and 20s, and eventually there comes a point when they have to decide whether to accept where they landed or make another attempt at changing direction.
Wilson Calls It A Kind Of Grief
Wilson said people often enter adulthood with a fairly specific script in their heads, believing that if they make the right choices in the right order, their careers, relationships and family lives will unfold accordingly.
As people move deeper into their 30s, however, that assumption becomes harder to maintain.
Wilson recalled asking a former manager what she had learned as she approached 40, and she told him one of the biggest lessons was simply that life would not look the way she once thought it was supposed to look.
He said that realization can feel like grief, although not necessarily grief in the sense of constant sadness or depression. Instead, it is the process of accepting that certain people, relationships, ambitions or versions of the future are simply not going to materialize in the form once imagined.
There is something very recognizable about that idea because adulthood contains many losses that are not marked by a funeral or a dramatic ending. Sometimes the loss is simply recognizing that an old plan has quietly expired.
Morgan Says Some People Simply Disappear From Your Life
Morgan immediately related Wilson’s comments to the people he assumed would still be around by this stage of adulthood.
Some are still part of his life, he said, while many others are not.
Friends who once seemed impossible to imagine living without can eventually become people someone has not spoken to for five years, even if they remain connected through Instagram or Facebook.
Morgan said younger people often picture themselves raising families alongside lifelong friends, living near each other and carrying the same relationships forward indefinitely, only to discover that work, relationships, moves and ordinary life pull people in different directions.
He also connected the discussion to family loss, saying his own parents are gone and that he never imagined reaching 36 without them.
That kind of change is not failure, but it can still alter the picture someone once had of middle age. A person may reach the career or relationship they wanted and still discover that the people they expected to share those years with are no longer there.
His Career Almost Did Not Happen
Morgan said one major part of his own life eventually came surprisingly close to the future he had imagined.
He had wanted to work in entertainment for years and had also long assumed that around age 35 he would settle down with a partner and begin building a family life.
Today, he said, he is engaged and earning a living through content, although neither path unfolded neatly.
Morgan described spending more than a decade pursuing creative work through skateboarding videos, stand-up comedy and other projects, including moving to California, without seeing the breakthrough he had expected.
By his early 30s, he found himself running an online resale business that had become successful but was not the career he actually wanted.
He remembered waking up around age 32 and wondering how he had ended up there after trying for so many years to build something else.
Morgan eventually made content creation work professionally around age 33, but he said there had been many points when quitting would have seemed reasonable, and at times even continuing felt embarrassing to people around him.
One former relationship, he said, partly broke down because of the unconventional career he was still chasing.
His takeaway was not that persistence guarantees success, because it clearly does not, but that he would have had no chance of reaching the life he wanted if he had permanently abandoned it during the years when it looked unrealistic.
The Late 20s Can Become A Turning Point
Wilson described the mid-30s as a period of reflection, but Morgan said he believes the first major warning often arrives earlier, particularly for men around age 27.
That is when people suddenly begin realizing that 30 is no longer distant and start asking whether their current path is actually leading where they intended.
Morgan said he experienced that himself and reacted partly out of fear, eventually ending up in a business he had never planned to build because it offered security when his preferred career had not worked out.
He believes many people face some version of that decision between their late 20s and early 30s, but instead of seriously evaluating what they want, they suppress the discomfort and continue along whatever path already exists.
Wilson made a similar point, saying adulthood eventually forces people to ask who they actually want to be rather than simply following the identity or lifestyle that has been handed to them.
He said some people respond by changing, while others remain attached to an older version of themselves and gradually become stuck.
That may be one of the more useful parts of the conversation because disappointment in your 30s is not always about missing obvious milestones. Sometimes it comes from realizing that years have passed while you were living almost automatically.
Viewers Describe The Same Feeling
Morgan also read comments from viewers who appeared to recognize Wilson’s description immediately.
One person wrote about being 36 without a house, marriage, partner or children, while dealing with debt and loneliness.
Another person in their 40s said it was comforting to discover that others had gone through the same process and described the experience almost like moving through stages of grief before reaching acceptance.
Other comments mentioned aging parents, dead grandparents and major life events that simply never happened despite once feeling inevitable.
Morgan said those stories are difficult because people are often taught, directly or indirectly, to assume that certain milestones will simply arrive with age.
When they do not, people can feel as though they somehow failed, even when the truth may be far more complicated.
There is also an important difference between accepting reality and accepting defeat. Learning that one version of life is gone does not mean every future version has disappeared with it.
Morgan Says It Is Not Too Late To Change Direction
Morgan ended the discussion by encouraging people not to become permanently trapped by the realization that their life went differently than planned.
He said someone can be 32, 40 or 44 and still decide to attempt something new, while younger people who feel uncertain should keep enough stability to support themselves and pursue what matters to them alongside it.
His own recommendation was practical rather than romantic: work the safe job during the day if necessary, but continue building toward the thing you actually want instead of assuming the opportunity has passed.
Morgan said not everything in his life worked out the way he imagined, but his career eventually did, and failed relationships ultimately led him to a partner he now considers his best friend.
Wilson’s original message was less about chasing dreams and more about accepting complexity, yet the two perspectives fit together fairly well.
Growing older means giving up some imagined futures, but it also means becoming more honest about which remaining possibilities actually matter.
For Morgan, the mistake is not reaching 35 and discovering that life looks different than expected. The greater risk is recognizing that difference, deciding nothing can change, and then spending the next decade in a life you already know you do not want.
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