The Entrepreneurial Advantage:
Understanding How You Respond to Expectations
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The Entrepreneurial Advantage: Understanding How You Respond to Expectations: Descriptive Title of the Audio
The Entrepreneurial Advantage: Understanding How You Respond to Expectations: Most of us are very aware of people’s expectations of us, whether it be a simple task such as a spouse asking you to unload the dishwasher, right up to how we grow our company or manage our teams. We are very aware that these things need to be done, and it is expected of us to do these tasks.
Most of us are very aware of people’s expectations of us, whether it be a simple task such as a spouse asking you to unload the dishwasher, right up to how we grow our company or manage our teams. We are very aware that these things need to be done, and it is expected of us to do these tasks.
On the flip side of that coin is our own expectations of ourselves. That side is not really looked at. After all, if you want to do something, just do it, right?
Well, once again, it seems we aren’t all the same after all.
Gretchen Rubin, a highly acclaimed author, podcaster, and speaker specialising in happiness, habits, and human nature, noticed something fascinating while researching why some people consistently followed through on their goals while others struggled, even when they genuinely wanted to succeed.
Her observations eventually led to what she calls The Four Tendencies, a framework that explains how people respond to two types of expectations: outer expectations (what others expect of us) and inner expectations (what we expect of ourselves).
The science behind it all
Before exploring the Four Tendencies, it is important to understand what they are and what they are not.
Although they are often compared to personality tests, Gretchen Rubin’s Four Tendencies are not designed to measure personality, and they are not based in scientific approach or experementation. They do not attempt to describe whether someone is introverted or extroverted, creative or analytical, or emotionally expressive or reserved. Instead, the framework focuses on one specific behavioural question:
How do you respond to expectations?
Rubin identified that we all encounter two types of expectations throughout life. Outer expectations come from other people, such as meeting a client deadline, leading a team, or fulfilling family responsibilities. Inner expectations are the commitments we make to ourselves, such as launching a business, exercising regularly, or finally writing the business plan we’ve been postponing.
How we consistently respond to these two types of expectations determines our behavioural tendency.
Unlike traditional personality assessments, the Four Tendencies are not intended to place people into fixed boxes or predict every aspect of behaviour. Rather, they provide a practical lens for understanding motivation, follow-through, and decision-making, three qualities that directly influence entrepreneurial success.
Rubin herself describes the framework as a tool for self-knowledge that helps people build habits, meet goals, reduce unnecessary stress, and create systems that work with their natural behavioural patterns instead of against them.
When combined with Jonathan Cheek’s work (Professor of Personality Psychology) on personal and social identity, the framework becomes even more powerful. Cheek helps explain where our expectations come from (our values, relationships, and roles in society), while Rubin explains how we naturally respond to those expectations.
Together, they offer entrepreneurs a practical, science-informed way of understanding why they behave as they do and, more importantly, how they can develop strategies that improve performance without trying to become someone they are not.
To learn more about Jonathan Cheek’s research, read here first: Aspects of Identity Questionnaire (AIQ-IV)
Why does this matter?
Starting a business is filled with expectations. Investors expect results. Customers expect value. Employees expect leadership. Family members expect stability. Society often expects success.
Yet perhaps the most powerful expectations are the ones entrepreneurs quietly place on themselves.
Some founders thrive under deadlines but struggle when nobody is holding them accountable. Others will move mountains to achieve a personal vision, even if nobody else believes in it. Some instinctively question every rule before acting, while others resist almost any expectation altogether.
None of these responses are inherently right or wrong. They are simply different ways that people are wired to engage with the world.
Research consistently shows that personality and behavioural characteristics influence entrepreneurial behaviour and business outcomes. While no single personality guarantees success, understanding how you naturally make decisions, maintain motivation, and respond to pressure allows you to build systems that complement your strengths rather than constantly fighting against them.
Unlike many business environments where commercial success is viewed largely as an individual achievement, African entrepreneurs frequently balance business goals alongside family responsibilities, community obligations, cultural expectations, and social leadership. Success is rarely personal, it often carries the hopes of many others.
Researchers have argued that African entrepreneurs operate within multiple “expectational worlds,” where personal ambition intersects with social responsibility, ethical obligations, and community wellbeing. These external pressures shape business decisions just as much as market forces do.
This means understanding your own response to expectations is not simply an interesting psychological exercise.
If you constantly disappoint yourself despite being highly capable, there is probably a reason.
If you always meet client deadlines but never finish the strategic project you’ve promised yourself for months, there is probably a reason.
If your team sees you as stubborn, or if you feel paralysed whenever someone tells you what you “should” do, there is probably a reason.
The encouraging news is that these patterns are understandable and, more importantly, manageable.
Rubin’s framework identifies four broad tendencies:
- Upholders readily meet both inner and outer expectations.
- Questioners question all expectations and act only when something makes logical sense to them.
- Obligers easily meet outer expectations but often struggle to meet their own.
- Rebels resist both inner and outer expectations when they feel their freedom or identity is being constrained.
Each tendency brings enormous strengths into entrepreneurship, but each also carries predictable blind spots.
Upholders: The Self-Disciplined Builders
Upholders readily meet both outer expectations and inner expectations. If they commit to a deadline, they are likely to meet it. If they set themselves a goal, they are equally likely to follow through. Rubin summarises their mindset as, “Discipline is my freedom.”
And let’s all take a moment to acknowledge the fact that we would all like the be this kind of unicorn…
For entrepreneurs, this often translates into exceptional consistency. Upholders naturally create routines, maintain productivity, and keep promises to both clients and themselves. They rarely need external accountability because their own internal standards are enough to keep them moving.
However, discipline can also become a weakness. Because Upholders feel compelled to meet every expectation, they may struggle to distinguish between urgent and important tasks. They often overcommit, find it difficult to say no, and can become overwhelmed by trying to satisfy everyone. When expectations begin to conflict, stress and burnout may follow.
For entrepreneurs who frequently balance business responsibilities alongside family, community, and social obligations, this tendency can become particularly demanding. Every request can feel like a legitimate obligation.
The key for Upholders is not learning more discipline (they already possess plenty of it). Instead, they should learn to prioritise strategically, establish healthy boundaries, and recognise that declining one commitment often protects a more important one.
Questioners: The Strategic Thinkers
Questioners approach every expectation with: “Why?”
Unlike Upholders, they do not automatically accept either internal or external expectations.
Before acting, they want evidence, logic, and understanding. Once they are convinced that something makes sense, however, they become highly committed because they have effectively transformed the expectation into one of their own.
This tendency often produces entrepreneurs who are analytical, curious, and highly innovative. They rarely accept conventional wisdom without examination and are constantly asking how systems can be improved. They enjoy researching markets, comparing alternatives, analysing risks, and making informed decisions.
These qualities are invaluable in entrepreneurship, where challenging assumptions often leads to innovation.
Yet, again, the same strengths can create obstacles.
Questioners sometimes fall into analysis paralysis. Because they seek the best possible answer, they may delay launching products, hiring staff, or entering new markets while gathering more information. The pursuit of certainty can unintentionally become a form of procrastination.
This tendency is especially relevant in rapidly changing African markets, where opportunities often favour those who are willing to act despite incomplete information. Waiting until every variable is known can mean missing valuable opportunities.
Questioners benefit from recognising that entrepreneurship rarely offers perfect certainty. Instead of asking whether they have enough information to guarantee success, they should ask whether they have enough evidence to make a well-informed decision.
Setting research deadlines, defining clear decision criteria, and embracing small-scale experimentation can help them maintain momentum without compromising their analytical strengths.
Obligers: The Dependable Leaders
Obligers readily meet outer expectations but often struggle to meet the expectations they place on themselves. Rubin describes their mindset as, “You can count on me, and I’m counting on you to count on me.”
This tendency is remarkably common. Obligers are reliable employees, supportive leaders, and trusted business partners because they naturally prioritise commitments made to other people.
In entrepreneurship, this often translates into exceptional customer service, strong team leadership, and a genuine desire to help others succeed. They rarely let clients down, consistently support employees, and work hard to honour their commitments.
Ironically, the challenge arises when nobody else is expecting something from them.
An Obliger may consistently deliver client projects while postponing strategic planning for months. They might spend all day solving employee problems but never make time to work on the long-term vision of the business. Their own priorities repeatedly fall to the bottom of the list.
Over time, this can lead to frustration, exhaustion, and what Rubin refers to as Obliger-rebellion; a point where years of meeting everyone else’s expectations suddenly result in resistance, burnout, or withdrawing from responsibilities altogether.
For entrepreneurs, accountability is often the solution. Mastermind groups, business coaches, mentors, advisory boards, or even publicly committing to business goals can transform important personal objectives into external commitments. Once accountability exists, Obligers often become extraordinarily consistent.
Rebels: The Independent Innovators
Rebels resist both outer expectations and inner expectations whenever they perceive them as limiting their freedom or identity. Their response is driven less by obligation and more by choice. Their mindset is captured in Rubin’s phrase: “You can’t make me—and neither can I.”
At first glance, this might appear incompatible with entrepreneurship. In reality, many highly innovative founders display strong Rebel characteristics.
Rebels value independence, creativity, authenticity, and autonomy.
They dislike unnecessary rules, challenge conventional thinking, and are often willing to pursue ideas that others dismiss. These qualities enable them to disrupt industries and discover entirely new ways of solving problems.
However, routine can become their greatest challenge.
Administrative tasks, repetitive systems, and externally imposed deadlines may feel restrictive, even when they are essential for business growth. Rebels often begin projects with enormous enthusiasm but lose interest once the work becomes predictable.
Traditional productivity advice frequently fails because Rebels resist being told what they “should” do, even by themselves.
Instead, they perform best when their work aligns with their identity. Rather than telling themselves, “I have to finish this proposal,” they are more motivated by, “I’m the kind of entrepreneur who delivers exceptional solutions.” Framing actions as expressions of personal identity rather than obligations helps preserve the sense of autonomy that drives them.
For Rebel entrepreneurs, flexibility is a strength rather than a weakness. Building businesses that allow for creativity, delegating routine administrative work where possible, and connecting daily actions to a larger mission can unlock remarkable innovation while maintaining momentum
A Final Thought
No tendency is better than another, and none determines whether an entrepreneur will succeed. Every tendency brings unique strengths to business, while each also faces predictable challenges. The goal is not to change your natural response to expectations but to understand it well enough to design habits, systems, and accountability structures that help you perform at your best.
Teagan specialises in Copywriting, Public Relations, Social Media Marketing and Blogging. Teagan uncovers the deeper “why” behind every venture. She believes that every person and project has a unique story, and nothing excites her more than transforming these narratives into compelling content that demands to be shared with the world.
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