Why Smart Entrepreneurs Stay Stuck | Joel Rickard

Ambition is often praised as an unquestioned virtue. We admire people who build companies, take risks, reinvent themselves, and push beyond conventional limits. Yet ambition can also carry a quieter question beneath it: am I doing this because I genuinely want to grow, or because some part of me is still trying to prove that I am enough?

My conversation with Joel Rickard explored that tension from several angles. Joel is a leadership coach and founder of the online community Fourdermental, where he works largely with entrepreneurs and ambitious professionals. His own path has been anything but linear. He grew up in rural New Zealand, studied aerospace engineering in Germany, worked in property development, and gradually became more interested in psychology, behavior, and the internal forces that shape how people work and live.

One of the most interesting themes in our conversation was imposter syndrome. Joel defined it as the fear that the version of ourselves we present to the world is somehow false and that, if people really knew us, they would find us lacking. It is not simply nervousness. It is the deeper fear that we are not enough as we are.

This often appears in ambitious people because ambition constantly pushes them into unfamiliar territory. A person receives a larger role, higher fee, bigger client, or greater responsibility and suddenly feels exposed. The discomfort is partly healthy because it indicates growth. Yet ambition can also be driven by the same insecurity. A person may chase success precisely because they are trying to prove that they deserve to be there.

This creates a difficult cycle. Achievement temporarily reduces the insecurity, but it rarely removes it. The next opportunity simply creates another test.

Joel believes one reason this happens is that people identify too strongly with what they do rather than who they are. The entrepreneur becomes the business. The speaker becomes the applause. The executive becomes the job title. When identity depends heavily on performance, every setback becomes personal.

One way to reduce this pressure is to shift attention outward. Instead of asking whether we deserve to be in the room, we can ask what the situation requires from us. Joel described receiving responsibility for a major property project while feeling underqualified. The fear was real, but focusing endlessly on whether he belonged would not help the project succeed. His task was to look at the work in front of him and do the best job possible.

That change in attention is simple but important. Imposter syndrome is intensely self-focused. We wonder how we appear, whether others are judging us, and whether they will discover our weaknesses. Focusing on contribution interrupts some of that internal noise.

Comparison makes the problem worse. We often assume we are comparing ourselves with other people, but Joel suggested that the more damaging comparison is usually with an imaginary version of who we think we should already be. Social media certainly influences that picture. We see someone else appearing confident, successful, productive, and calm, then judge ourselves for not feeling the same way.

The problem is that we are comparing our internal experience with someone else’s external presentation. We see their result and feel our uncertainty.

Much of this begins early in life. Joel spoke about the small conditions children can attach to love, attention, and approval. A parent may praise a child heavily for achievement or constantly point out how something could have been improved. The intention may be encouragement, yet the child can learn that acceptance depends on performance.

That child becomes an adult who believes they must be exceptional to feel secure. Perfectionism, overwork, undercharging, hesitation, and constant validation-seeking may all grow from that same belief.

Joel’s coaching focuses less on teaching new business strategies and more on understanding why people fail to implement strategies they already know. Many entrepreneurs know they should make sales calls, increase prices, communicate more clearly, or spend less time procrastinating. The obstacle is often not information.

It is fear.

Someone may know that their service is worth more but still feel unable to charge more. Beneath the pricing decision may be a belief that they are not valuable enough. Joel described working with an entrepreneur who already had evidence that his product produced results, yet continued undercharging because he believed he needed to offer more before he could justify a higher price.

Once that belief changed, the behavior followed. He raised his rates and quickly reached a new revenue level without redesigning the business itself.

This does not mean positive thinking magically produces money. Joel was clear that beliefs must still be tested against reality. Confidence without competence can become delusion. The goal is not to convince ourselves that everything is possible, but to examine whether an old belief is preventing us from testing what might actually work.

That distinction matters because staying the same also carries risk. People are often highly aware of what might go wrong if they change and almost completely unaware of what they lose by refusing to change.

Raising prices may risk losing customers, but never raising them may keep a business permanently underfunded. Accepting a larger opportunity may create stress, but avoiding it may preserve the same limitations for years. Remaining comfortable has an opportunity cost.

This led to one of the broader ideas in our conversation: there are no perfect solutions, only trade-offs.

Every meaningful choice carries a cost. Entrepreneurship may provide freedom while demanding time. Career growth can increase financial security while placing pressure on relationships. A person can spend more time with family, but that time has to come from somewhere else.

Joel sees this clearly in the men he works with. Many feel responsible for providing financially while also wanting to be present husbands and fathers. They work longer because they care about the future of their families, yet the family may experience that effort as absence.

The problem is often less about the workload itself than the silence surrounding it.

Men frequently believe they must absorb pressure quietly. They keep working, keep providing, and avoid saying that they are struggling. Their partner sees someone continually choosing work, while the man may internally believe he is sacrificing precisely for that relationship.

Communication can change that dynamic. A difficult business period can be described as a season rather than an undefined permanent condition. A person might explain that the next six months require greater focus, why that focus matters, and what the relationship still needs during that period.

This does not eliminate the trade-off, but it makes the trade-off visible and shared.

Joel believes men also need to judge themselves less harshly. The pressure does not always come directly from circumstances. It often comes from the story attached to them: I should be further ahead, I should be stronger, I should have this figured out.

That judgment creates another layer of difficulty. The business challenge remains, but now the person is also criticizing themselves for struggling with it.

Acceptance does not mean giving up. It means acknowledging the starting point honestly enough to move from it.

The same principle applies to self-awareness. Joel does not believe self-awareness is overrated, but awareness without action can become another form of stagnation. People can spend years analyzing childhood patterns, personality types, habits, and emotional triggers without changing anything meaningful in their lives.

Personal development can become sophisticated procrastination.

A useful insight should eventually produce a different choice, even if that choice is small. Otherwise, self-awareness becomes another place to hide.

This is also how Joel approaches coaching. He does not see the coach primarily as someone who gives answers. He sees the role more as helping another person notice what they have been unable to see.

The distinction is important because advice is easy to reject. When someone tells us what to do, our instinct may be to defend the behavior or explain why the suggestion will not work. When we arrive at the conclusion ourselves, ownership becomes much stronger.

A good coach, in Joel’s view, asks questions that help people uncover their own contradictions. Why do you say you want growth while avoiding the sales calls that could create it? Why do you say your work is valuable while pricing it as though it is not? Why are you working to provide for your family while refusing to tell them that you are overwhelmed?

The answer is rarely a lack of intelligence.

More often, it is an old belief operating quietly beneath the decision.

Near the end of our conversation, I asked Joel to choose between success and fulfillment. He chose fulfillment. I then asked ambition or peace, and again he chose peace.

Those answers might seem strange coming from someone who works with ambitious entrepreneurs, but they fit his philosophy perfectly. People frequently chase success because they believe success will finally create peace, freedom, belonging, or self-worth.

The danger is reaching the goal and discovering that the internal feeling never arrived.

Joel’s argument is not that people should abandon ambition. It is that ambition works differently when it comes from enoughness rather than deficiency. A person who already believes they are worthy can still build, compete, experiment, and pursue difficult goals, but the outcome no longer determines their identity.

That may be the healthier form of ambition.

Growth without constant self-rejection. Success without making success responsible for our emotional survival. Hard work without pretending that every other part of life can be neglected indefinitely.

There will always be trade-offs.

The real challenge is understanding which ones we are willing to make, communicating them honestly, and ensuring that the life we are building does not quietly consume the reasons we wanted to build it in the first place.