Learn your tendency to succeed: Are you an Obliger, Upholder, Questioner or a Rebel?

Written by Arno Jansen

Picture this: you’ve set your alarm early.

Determined to conquer the day, you get up nice and early. But you somehow find yourself distracted. Can be anything…. a never-ending to-do list, Instagram, YouTube shorts, etc.


Maybe you’ve meticulously planned your workweek, only to feel trapped by your own schedule, unable to break free, innovate and just breathe for a minute.

If this sounds familiar, don’t worry. We’ve all been there.

For years I was obsessed with learning productivity systems, tools, automation.

GTD, Bullet Journalling, Daily Trifecta, Pomodoro, Eat That Frog, I’ve tried them all.

These systems are battle-tested, but fall short for most Solopreneurs.


Because these system don’t take into account one key thing: your natural bias towards expectations.

Here’s the kicker:

Knowing your tendency to succeed, is the key to unlocking your full focus potential.

I really believe this.

It’s like having a personalized guide to navigate the twists and turns of your journey. It is your unique lens through which you view the world and make decisions.

You may have tried:

  • Rigid scheduling
  • Motivation hacks
  • Every productivity app under the sun

to boost your focus and productivity. Maybe they even worked for a while. But more likely than not, you found yourself right back where you started after a while. Feeling frustrated and overwhelmed.

That’s because these solutions don’t consider one critical factor —YOU!

At some point you have set, met and even exceeded goals, commitments or expectations. Other times, you have failed miserably. This happens.

But whether or not you meet expectations and commitments, is not determined by a roll of the dice.

Knowing your bias towards expectations can transform the way you work and find success. Not only will you understand yourself better, but you’ll thrive within your unique nature. That is your tendency to succeed.

Meet the 4-Tendencies-Framework: Unveiling Your Unique Approach to Success

This framework was developed by Gretchen Rubin. It divides people into 4 distinct personality types. It does so based on how they respond to inner and outer expectations.

Outer expectations are what others expect of you, such as deadlines, appointments, etc.

Inner expectations are what you desire from or expect of yourself.

Understanding how you respond to these tendencies helps you improve how you work and manage yourself. It also helps you work better with others.

Let’s explore each tendency, specifically through the lens of a self-starter.

The Upholder

An Upholder regulary meets both outer and inner expectations.

An Upholder tends to meet both inner and outer expectations. They thrive on structure and discipline, making them self-motivated achievers. Deadlines and rules are usually respected, and an upholder finds satisfaction in meeting their own goals.

Strengths for Solopreneurs

  • Upholders excel in creating and sticking to routines, which can lead to consistent progress.
  • Their reliability and ability to meet goals make them dependable entrepreneurs who can deliver on promises.

Challenges for Solopreneurs

  • They might struggle with flexibility and adapting to unexpected changes.
  • Over-reliance on rules can hinder innovation and taking risks.

Tip for Dealing with Upholders (Including Yourself)

  • Appreciate their dedication to schedules and structures.
  • When collaborating, offer clear expectations and deadlines.
  • Allow them some flexibility within a defined framework.

The Solopreneur perspective

  • Deadlines: Benefit from deadlines by using them as motivating tools. However, watch out for becoming overly stressed if deadlines are too tight or rigid.
  • Rules: Use rules to create efficient routines and maintain consistency. Be open to adjusting rules when necessary to adapt to changing circumstances.
  • Thinking Outside the Box: Upholders may feel more comfortable with structured thinking, but encourage them to explore unconventional ideas or approaches to business challenges.
  • Creating Habits & Routines: Easily establish habits, which can lead to steady progress. However, remember to infuse creativity to prevent monotony.
  • Setting Goals: Thrive when setting clear, measurable goals. Break larger goals into smaller, manageable steps for a sense of accomplishment.

Bottom line

If you’re an Upholder, consider setting specific milestones and deadlines for your business tasks. Create a detailed daily or weekly schedule that aligns with your goals, giving you a roadmap to success. Yet, be mindful of your tendency to stick too rigidly to routines. Allow room for experimentation and innovation to keep your business fresh and adaptable.

The Questioner

The Questioner will do it if it makes sense (to them)

The questioner seeks reasoning behind both inner and outer expectations. They value logic and efficiency. They will generally meet expectations if they align with their own understanding. In a way, they turn outer expectations into inner ones, by justifying it to themselves. They often question rules and seek to optimize processes.

Strengths for Solopreneurs

  • Excel in critical thinking and problem-solving.
  • Their ability to challenge the status quo can lead to innovative approaches and improvements.

Challenges for Solopreneurs

  • Over-analysis and indecision can hinder progress.
  • They can resist tasks that don’t immediately make sense to them.

Tip for Dealing with Questioners (Including Yourself)

  • Provide clear explanations for why certain tasks or goals are important.
  • Encourage their curiosity and involve them in decision-making processes.

The Solopreneur perspective

  • Deadlines: Questioners may need a clear rationale for deadlines. Set deadlines with thoughtful explanations to motivate them.
  • Rules: Embrace rules that align with their logic, and be open to discussing and adapting rules when necessary.
  • Thinking Outside the Box: Questioners will challenge norms. Inspire them to use their creativity when brainstorming innovative solutions to business challenges.
  • Creating Habits: Benefit from external accountability when forming new habits. Pair habit-building with fulfilling external commitments.
  • Setting Goals: Thrive when goals align with your vision. Encourage them to set goals that challenge their own assumptions.

Bottom line

Use your tendency by researching market trends, customer preferences, and industry best practices. Set goals that align with your logical reasoning. Seek opportunities to innovate and optimize processes within your business.

But do not to get stuck in endless analysis. Balance your hunger for information with action to propel your business forward.

The Obliger

The obliger meets outer expectations, but struggles with inner expectations.

Meeting outer expectations is often not a problem. Meeting inner ones is. They thrive on external accountability and may neglect their own needs while fulfilling obligations to others.

Quotes such as “I will always make time for others, but not for myself” fit the Obliger tendency.

Obligers can also struggle to let go of work, especially when meeting outer expectations, such as client deadlines.

Strengths for Solopreneurs

  • Excel in meeting client and customer needs.
  • Their responsiveness and commitment make them reliable solopreneurs who value customer satisfaction.

Challenges for Solopreneurs

Tip for Dealing with Obligers (Including Yourself)

  • Provide external accountability and support.
  • Encourage them to set boundaries.
  • Make time for both personal and business-related tasks.

The Solopreneurs perspective

  • Deadlines: Flourish with external deadlines, but may struggle with self-imposed ones. Seek external accountability for self-set goals.
  • Rules: Create rules and routines that provide structure. Build rules for self-care and balanced work-life integration.
  • Thinking Outside the Box: Challenge Obligers to explore creative ways to meet external expectations. Do so while nurturing their desire to help others. Encourage them to brainstorm innovative solutions. If you need to encourage yourself, find ways to turn inner expecations into outer ones. External accountability is a great way to do that.
  • Creating Habits and routines: Use external accountability when forming new habits. Pair habit-building with fulfilling external commitments.
  • Setting Goals: An obliger will focus on goals set by others, but as a solopreneur you need to take control of your own goals. Remind yourself of the importance of setting and achieving your own goals to ensure personal and business growth.

Bottom line

If you are an Obliger, you thrive on external accountability. Working with an accountability partner, coach or mentor can help you stay on track with your goals.

Make sure to carve out dedicated time for both work and self-care to avoid burnout. Also, be mindful of the tendency to overcommit to external obligations.

Set clear boundaries and learn to say no when necessary, ensuring you have the time and energy to focus on your business’s long-term success.

The Rebel

Resisting Inner and Outer Expectations

How Rebels Approach Expectations

Rebels resist both inner and outer expectations. They value autonomy and freedom. They seek to defy traditional norms and expectations. They thrive on independence and self-expression.

Strengths for Solopreneurs

  • Rebels bring a fresh perspective and creative energy to their work.
  • Their ability to challenge conventions can lead to unique and innovative business ideas.

Challenges for Solopreneurs

Tip for Dealing with Rebels (Including Yourself)

  • Frame tasks as opportunities for creative expression and freedom.
  • Allow space to contribute unique ideas and approaches.

Benefits and Challenges with Solopreneurship

  • Deadlines: Approach deadlines with a sense of independence. Embrace flexibility while setting boundaries to ensure timely progress.
  • Rules: Rebels may resist strict rules. Offer guidelines that provide a sense of direction without stifling autonomy.
  • Thinking Outside the Box: Rebels naturally think outside the box. Channel their creativity into innovative solutions that align with their business goals.
  • Creating Habits: Rebels can create habits that align with their sense of identity and freedom. Focus on habits that align with their values.
  • Setting Goals: Rebels thrive with self-determined, meaningful goals. Frame business goals as opportunities for personal growth and expression.

Bottom line

If you identify as a Rebel solopreneur, embrace your innate creativity and independent spirit. Experiment with unconventional business strategies for example. Set flexible goals that align with your values and provide a sense of purpose.

But, don’t resist structure entirely. Routines and guidelines can help you stay consistent and achieve your goals.

Which one are you?

Learning about this framework, and figuring out your natural tendency, is a big step to leading yourself, in a nice balance between ambition and joy.

If after reading this, you have no idea what tendency fits you, there is a free test you can do on Gretchen Rubin’s website. You will have to anwer a dozen multiple-choice questions to find your tendency.

According to Rubin, every person fits into 1 category naturally. Through awareness and deliberate effort, you can adopt benefits from other tendencies.

After learning about this framework, I did not agree with that last statement. I found myself to show behaviours of all different tendencies. Both good and not-so-good.

Then again, the free test on her website showed my tendency to a Questioner, so I suppose it makes sense I question the expert on the topic 🤣

So, now what?

Keep in mind that no tendency is best or worst. Each tendency has its challenges and opportunities. Knowing your natural tendency shapes your approach to productivity, goal-setting, and collaboration.

Armed with this knowledge, you’re ready to create a way to work that fits you best. And adapt the generic productivity advice and hacks that did not work for you (until now).

My personal journey of Solopreneurship has been as much about understanding myself better. This framework helps me with that, almost daily. I hope it does the same for you.

I’m rooting for you! 🙌

Looking to get more productive, focused, and resilient?

Join my free Focus Finder email course to transform yourself from deeply distracted to fully focused.

    Looking to get more productive, focused, and resilient?

    Join my free Focus Finder course and go from deeply distracted to fully focused.

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