Thinking About Overthinking | Alex Ostergaard

Overthinking is usually described as a problem to be eliminated. We are told to stop analyzing, quiet the mind, make faster decisions, and move forward. The advice is understandable, especially for anyone who has spent hours replaying a conversation, rehearsing an uncertain future, or turning one difficult choice into seventeen competing possibilities. Yet this framing assumes that overthinking is itself the problem. My conversation with Alex Ostergard, author of Dissolving Overthinking, offered a more compassionate and useful possibility: overthinking may be less an enemy to defeat and more a signal worth understanding.

Alex does not claim to have conquered overthinking. In fact, he openly admits that he still does it. He overthought his preparation for our podcast about overthinking, which is either deeply ironic or excellent brand consistency. The difference is that he no longer treats the appearance of excessive thought as evidence that something has gone wrong. Instead, he has learned to ask what the thinking is attempting to protect.

This distinction sits at the center of his work. Overthinking, in Alex’s view, often emerges when some part of us feels uncertain, exposed, ashamed, or unsafe. The mind accelerates because it believes more analysis will produce control. Sometimes that thinking is useful. It helps us solve problems, prepare carefully, anticipate consequences, and make better decisions. At other times, the thought process continues beyond usefulness. It creates no solution, inspires no action, and provides no genuine clarity. It simply generates more thought.

That is where thinking becomes overthinking.

Alex defines it as thinking beyond the point of usefulness. Healthy problem-solving tends to move somewhere. It leads to a decision, an experiment, a conversation, or a practical next step. Overthinking circles the same territory while creating greater anxiety. The mind appears active, but the person remains stuck.

This perspective makes overthinking feel far less like a personal defect. It becomes a deeply human response to uncertainty, one that is often connected to identity, belonging, perfectionism, and the desire to control how others perceive us. These themes did not begin for Alex during his corporate career or while writing his book. They appeared much earlier, during a childhood shaped by several cultures and a persistent question about where he belonged.

Alex describes himself as the product of a cultural threesome: an English mother, a Danish father, and a childhood in France. The phrase is deliberately provocative, but the experience behind it is familiar to many people raised between cultures. In France, he thought of himself as English and Danish. When he later moved to Denmark, he discovered that he did not feel entirely Danish. In the United Kingdom, he realized he did not share many of the references, habits, and experiences that would have made him feel fully English either.

His rugby nicknames captured the contradiction perfectly. In France, he was “Rosbif,” a label for the English. In Denmark, he became “Frenchie.” In Britain, he was “Danish Pastry.” Everywhere he went, others identified the part of him that came from somewhere else.

Growing up across cultures brought enormous advantages. Alex became multilingual, adaptable, and comfortable moving through international environments. Yet it also created a quieter tension around identity. A child who feels different often becomes highly attentive to the reactions of others. Belonging can begin to feel conditional, something that must be earned through achievement, adaptation, or the successful performance of whichever identity is most acceptable in the moment.

Another formative experience occurred when Alex was eight years old. He received a score of eighteen out of twenty, an excellent result within the French educational system. He was thrilled and eagerly waited for his father to return home. His father looked at the paper and asked why he had not received twenty out of twenty.

Alex is careful not to blame him. His father was loving and probably intended the comment as encouragement. He may have forgotten the exchange almost immediately. Alex did not. He returned to his room with a quiet determination that next time, he would earn the perfect score.

That moment became an internal standard.

For years, Alex chased his symbolic twenty out of twenty through education, sport, professional achievement, recognition, and status. His sense of worth became connected to performance. As long as something came naturally, he felt capable. When difficulty demanded patience, practice, or the possibility of visible failure, avoidance became safer. If he tried and struggled, the struggle might reveal that he was not exceptional. It was easier to disengage than to risk discovering that effort would still produce an imperfect result.

This pattern is common among high achievers. People often assume that achievement is driven primarily by ambition, discipline, or a desire for success. Those elements may be present, but beneath them there is sometimes a more vulnerable pursuit. The person is chasing a feeling: worthiness, approval, security, admiration, or proof that they belong.

Achievement can provide that feeling briefly. The problem is that the effect rarely lasts.

A promotion offers relief until the next promotion appears. Praise feels satisfying until attention moves elsewhere. A prestigious employer provides status, but it also creates the fear of losing that status. The very thing that produces reassurance becomes another source of anxiety.

Alex experienced this vividly when he was offered a job at Google. He remembers receiving the call in his living room in Copenhagen and immediately celebrating. The role represented far more than employment. When he told his father, he finally received the response he had unconsciously wanted since childhood: uncomplicated pride, without correction or qualification.

He had earned his twenty out of twenty.

Working for Google also changed how other people responded to him. Conversations became more attentive. People leaned forward. The company’s reputation seemed to transfer some of its value onto him. Alex admits that he enjoyed this and began casually mentioning where he worked whenever the opportunity appeared. The title gave him validation, but it also increased his dependence on external identity.

Once worth becomes attached to a role, losing the role feels like losing the self.

Inside Google, Alex found himself surrounded by highly capable people. The prestige that had initially made him feel secure soon created another question: did he really belong there? He worked longer hours, replayed conversations, checked emails repeatedly, and became increasingly strategic about how he was perceived. From the outside, these behaviors could have looked like diligence. Internally, they were attempts to control uncertainty.

The same pattern later continued at Uber. Alex worked intensely for months in pursuit of a promotion, selecting projects carefully and trying to position himself for advancement. When his manager explained that the organization did not have the necessary headcount and that he would need to wait for another cycle, something in him gave way. He realized that he would have to repeat the entire performance again.

He experienced a panic attack in the office bathroom, searching for a meditation app while struggling to look at his phone. A doctor later told him that he was burning out and needed to step away from work.

Burnout is usually discussed as a failure of coping, workload management, or organizational design. In Alex’s case, it was certainly painful and disruptive, but it also became an interruption he had been unable to create voluntarily. His body stopped cooperating with the story his mind had been telling. The message was simple: this cannot continue.

Alex now describes burnout as a gift, though he does not romanticize the experience itself. At the time, it felt humiliating. He experienced anxiety and shame and avoided telling many of his friends. Only later could he see that the breakdown changed the direction of his life. It contributed to his departure from corporate work, the creation of his own business, and eventually the writing of his book.

His interpretation reflects a broader philosophy: life can be understood as happening for us rather than merely to us. Alex does not present this as an objective truth. It is a chosen orientation. It allows people to ask what an experience might reveal or create, even when the experience itself remains unpleasant.

This does not mean that every hardship is secretly good. It means that human beings have some capacity to shape the meaning that follows hardship.

The body, in this sense, becomes an important source of information. Alex’s burnout was not evidence that his body had betrayed him. It was evidence that it had noticed something his conscious mind continued to avoid. He had developed better inbox systems, improved his productivity, and found increasingly sophisticated ways to maintain control. Yet he had not dealt with the deeper fear driving the behavior.

This leads to the first major idea in Dissolving Overthinking: overthinking is a protection mechanism. The mind is not necessarily trying to make life difficult. It is trying to prevent embarrassment, rejection, uncertainty, failure, or emotional pain. Once this is recognized, the internal conversation can change. Instead of asking, “How do I stop doing this?” we can ask, “What is this trying to protect me from?”

The second idea is that overthinking is a form of control. Preparing for a podcast, for example, is sensible. Rehearsing every possible answer in order to guarantee a certain impression is something different. The preparation is no longer serving the conversation. It is attempting to manage perception.

Perfectionism often functions in the same way. It may appear to be a commitment to excellence, but it can also be an effort to control how others respond. People-pleasing is another example. By becoming agreeable, useful, or endlessly accommodating, a person attempts to prevent disappointment, conflict, or rejection. The behavior creates the appearance of harmony while quietly disconnecting the person from their own needs.

The third principle may be the most psychologically revealing: overthinking is often under-feeling.

Alex illustrated this through an experience at Toastmasters. He volunteered for an impromptu speaking exercise shortly after completing a paid public-speaking engagement. Feeling confident, he walked to the front of the room. The host praised him, raising the audience’s expectations. Alex attempted humor, but the room remained silent. He froze, lost his words, and eventually returned to his seat feeling deeply embarrassed.

The moment lasted less than a minute. His mind replayed it for weeks.

He revisited the scene while brushing his teeth, making breakfast, and waking during the night. At first, the repetition appeared to be problem-solving. He was analyzing what happened, what people thought, and how he could prevent it from happening again. Eventually, he recognized that the thinking was doing everything except allowing him to feel the shame.

The mind was not looking for a solution. It was looking for an escape route.

This may explain why certain thoughts return even after they have been thoroughly analyzed. The person believes the answer remains hidden somewhere within the logic of the event. In reality, the unresolved element may be emotional. No amount of explanation can fully replace the experience of feeling disappointment, grief, fear, humiliation, or uncertainty.

Thinking is an extraordinary tool, but it has limits. We cannot think our way out of grief. We cannot logically prove ourselves into permanent self-worth. We cannot always analyze our way into peace.

Sometimes the feeling must be felt.

This does not mean indulging every emotion or allowing it to determine behavior. It means developing enough capacity to experience discomfort without immediately escaping into analysis. Alex suggests that much anxiety is intensified by the fear of anxiety itself. The person feels an uncomfortable sensation, decides it must disappear, and becomes anxious about being anxious. Resistance multiplies the original experience.

Acceptance changes the relationship. The emotion may remain unpleasant, but it loses some of its authority when it no longer needs to be fought.

The fourth principle is that overthinking can become a doorway into deeper healing. Because excessive thought frequently points to a vulnerable area, it can reveal where a person is still seeking control, approval, certainty, or proof of value.

Alex encountered this after publishing his book. The launch initially went well, and positive reviews appeared on Amazon. He found himself repeatedly refreshing the page, watching the numbers increase and enjoying the identity of being a successful author. He imagined introducing himself at social gatherings and being taken more seriously because of the book.

Then Amazon removed it.

What followed was several weeks of appeals, emails, frustration, and intense overthinking. The irony of having a book about overthinking removed and then overthinking the removal was not lost on him. Yet this time, he had enough awareness to look beneath the obvious frustration.

He realized that each time he refreshed the review page, it was not simply an author checking his work. It was an eight-year-old boy looking for his twenty out of twenty.

The book had become his new Google.

This insight captures how easily an old pattern can return in new clothing. A person may leave one prestigious job, complete years of personal development, and genuinely believe they have detached their worth from achievement. Then the same need quietly attaches itself to a business, a book, a relationship, a social media following, or even the identity of being healed.

The object changes. The emotional bargain remains the same.

Alex’s experience also reveals one of the risks within the self-development industry. Self-awareness can become another performance. A person who once proved their worth through promotions may begin proving it through therapeutic vocabulary, spiritual practices, or the amount of inner work they have completed. Growth becomes another scorecard.

This is the self-awareness trap. Awareness is essential for change, but awareness alone does not guarantee freedom. A person can become highly articulate about their patterns while continuing to live inside them. They may know the origin of every insecurity and still use that knowledge as another reason to judge themselves.

The industry often reinforces this by presenting people as machines requiring constant improvement. Something is always broken, blocked, wounded, misaligned, or waiting to be optimized. The customer is encouraged to believe that the next book, course, retreat, or framework will finally produce the complete version of the self.

Alex offers a gentler interpretation. Human beings are not machines that need endless repair. Growth is already part of our nature. The work may involve removing what obstructs that growth rather than continually adding new layers of self-improvement.

You do not make grass grow by pulling on it.

This philosophy helps explain the title Dissolving Overthinking. Alex does not want to defeat, crush, tame, or overpower the mind. Those verbs create another battle, which often produces even more thought. Dissolving suggests that the problem changes as the relationship changes.

He illustrates this with a story about a king and an untamable white horse. Experts arrive with chains, ropes, whips, and cages, but none can control it. Eventually, someone is seen riding the horse freely. When asked how he tamed it, the rider explains that he did not. He listened to what the horse needed and allowed it to run.

The metaphor reflects Alex’s relationship with his own mind. He does not attempt to silence overthinking through force. He listens, experiments, and tries to understand what the mind is communicating. At times, he describes this as dancing with it.

There is an appealing humility in this approach. It does not promise permanent mental quiet. It recognizes that thought is part of being human. The goal is to develop a different relationship with it, one that includes curiosity, humor, and enough distance to determine whether the thinking is useful.

Technology adds another dimension to this conversation. Artificial intelligence can provide extraordinary clarity, generate possibilities, and support decision-making. It can also become an endlessly available partner in rumination. A person can ask one question, receive five considerations, request twelve alternatives, discover three new concerns, and still be awake at four in the morning asking whether option seven aligns with their authentic self.

AI can become a sophisticated mirror.

The way people use it may reveal how they relate to uncertainty. Some use it to gather information and move into action. Others use it to avoid responsibility for a decision. They repeatedly ask for reassurance, hoping the machine will eventually provide certainty that life cannot offer.

Alex acknowledges doing this himself. At times, he has asked AI whether his feelings were acceptable or whether a decision was right. The technology can be helpful, but it may also expose an unwillingness to trust one’s own judgment.

This challenge will likely become more significant as AI alters professional identities. Many people have attached their sense of value to being an accountant, writer, analyst, designer, manager, or specialist. As technology changes the tasks associated with these roles, the disruption may extend beyond employment. It may become a crisis of identity.

The question will no longer be only, “What work will I do?” It may become, “Who am I without the work that proved my value?”

Social media creates a related dynamic. It can provide entertainment, education, connection, and inspiration. It can also become a convenient escape from the discomfort of the present moment. The distinction depends less on the platform itself and more on the relationship a person has with it.

Alex resists the simplistic claim that everyone using social media is addicted or avoiding life. Yet he points out that the platforms are built by highly skilled teams whose success depends on retaining attention. Once an app is opened, individual intention is competing with systems built to prolong engagement.

The most useful question may not be whether social media is good or bad. It may be whether the experience is producing greater clarity, connection, and enjoyment, or whether it is creating agitation, comparison, and another layer of mental noise.

Again, the technology becomes a mirror.

Near the end of our conversation, I presented Alex with several rapid choices. He selected freedom over Google, experience over books, self-trust over confidence, authenticity over validation, nature over the city, and intuition over logic.

His answers reflected the direction of his life rather than a rejection of what came before. He still values books, cities, logic, achievement, and professional identity. He simply understands their limits more clearly. Books can provide insight, but experience creates wisdom. Confidence often arrives after action, while self-trust allows action before confidence appears. Logic is useful, but intuition may perceive something that analysis cannot fully articulate.

Perhaps the most important shift is from control to trust.

Overthinking promises safety through prediction. If every possibility can be analyzed, perhaps nothing painful will happen. Yet life refuses to become completely predictable. Careers change. books disappear from platforms. Audiences remain silent. Promotions fail to arrive. Identities evolve. Technology disrupts the professions around which people have built their lives.

No amount of thought can remove uncertainty from being human.

What thought can do is help us prepare, understand, and choose. The challenge is recognizing the point at which preparation becomes avoidance and analysis becomes resistance. Beyond that point, another form of intelligence may be required: the willingness to feel, act, trust, and allow experience to provide information that thought alone cannot produce.

Alex’s work does not ask people to become less intelligent or reflective. It invites them to stop using intelligence as a weapon against themselves. It asks them to meet thought with curiosity rather than hostility and to recognize that the mind’s frantic activity may be an imperfect attempt to protect something vulnerable.

The child seeking a perfect score needs to know that he matters without one.

The professional rehearsing every interaction may not need a better script. She may need permission to be imperfect and remain worthy of respect. The person refreshing reviews, checking messages, or repeatedly consulting AI may not require more information. They may need to trust that uncertainty can be survived.

Overthinking, viewed this way, is less a malfunction than a messenger. It points toward the places where control has replaced trust, achievement has replaced worth, and analysis has replaced feeling.

The aim is to understand the message well enough that it no longer needs to shout.