Six Ways to Dare Your Life Forward

How do you find the courage to embrace your next daring action?

For folks facing a career transition, significant life change, or simply looking for renewed momentum, initiating a bold and daring step is one way to propel yourself forward into the life you truly desire for yourself and your loved ones.

A few years ago, I dared to leave a successful corporate career. I left behind well-known and respected colleagues, financial security, and the processes and skills I had learned to master over time. 

Indeed, leaving this career behind at the age of fifty-one – with a name that many felt was abnormal – resonated with me as not reasonable, silly, careless, or reckless. Many colleagues wondered if I was being coerced into the decision. Still, others believed that it was a daring step, one they wished they would take.

I realized that others’ reactions were each a reflection of their own beliefs, fears, hopes, and dreams. I knew I was daring to take a step when I decided to launch Point North International. On the other hand, was it only a daring step or a wise one- one that enabled me to truly live rather than merely exist? I jumped into the unknown with the conviction that as long as I was living, there would always be an option to land somewhere new, somewhere that would always make sense. I dared. And I never looked back.

Upon reflecting on my daring decision, I discovered six ways in which I suggest all career transitioners begin to dare.

Six Ways to Dare Your Way Forward

1. Dare to invest in you.

All serious daring starts from within

Eudora Welty

You are your safest investment. Nothing else in your life is as anchored to you as…well, you! 

Investing in yourself means elevating how you prioritize your learning, your well-being, your health, and your own excellence. This may mean that you choose to invest time and money to pursue what you deem most important, learning, discovering, practicing, and developing yourself into the version of yourself that can best serve others while serving the highest, most powerful version of yourself. You are your greatest asset and your most significant leverage point.

Don’t stop at average as you develop your professional skills while developing the person you are and the habits that will sustain you. Dare to be excellent. Dare to be extraordinary.

2. Dare to face your fears.

Man cannot discover new oceans unless he has the courage to lose sight of the shore.

Andre Gide

The role of fear is an important one, often keeping us safe from harm and even heartbreak or disappointment. But stronger than the mind’s practice of dealing with fear is the payoff of overcoming something that once made you fearful to face.

Bring to mind something that you fear in your career transition. Is it the loss of finances? Isolation from your peers? The perpetual uncertainty that may come with entrepreneurship? The fear of shame, of not being good enough, the fear of failure?

Rather than hiding from these fears, convinced that they will bring you pain, consider identifying:

  1. What is this fear trying to tell me?
  2. Where is this fear coming from?
  3. What techniques can I learn to deal with this fear?
  4. How can I play with this fear?

Stop being manipulated and stopped by your fears. There are several simple techniques to face them and overcome them. Instead, use them to propel your action and turn them into positive encouragement and proof that you are doing exactly what you should. Remember: you are not your fears. They are merely an indication; an invitation. Confronting them is a choice, as is suffering.

3. Dare to believe in yourself.

If you have a dream, don’t just sit there. Gather courage to believe that you can succeed and leave no stone unturned to make it a reality.

Dr. Roopleen

Believing in yourself creates a ripple effect of belief; your conviction will inspire your team, children, partner, friends, and family to believe in you, too. If one of your values is recognition, or if you have dealt with low self-esteem or discouraging words from others in the past, this is especially important for you. 

Dare to be open, honest, and purposeful about sharing what you believe. Ask questions. Explore opportunities. Volunteer and put yourself into new situations and communities.

Raise your self-confidence and get used to your new reality by visualizing it now, feeling it now and believing it now. Your brain doesn’t distinguish between what you feel and what is- so feel it. Make it real and trust that you are already making the impact you’re here to make. Finally, if you tend to see the glass half empty most of the time, try pouring the water into a smaller glass and move on.

4. Dare to take action.

When you can’t predict or control the outcomes in life, then there comes the time when you need to show your courage.

Brené Brown

Take. The. Step.

Sign up for that new program you’ve been eyeing. Speak up to solve a conflict or resolve the tension. Spark a discussion with your team leader, manager, or colleague to right a wrong or clarify the message they are giving. Register for that new activity. Join the team. 

Procrastinating is our fear’s way of keeping us safe – after all, how can we fail if we don’t take action – but safe means we are not moving toward our vision or our best version of ourselves. 

Taking that step forward may not always offer 100% satisfaction. But taking no action will absolutely guarantee 100% stagnation. 

Now is always the best time to take action. Test. Pilot. Try

5. Dare to ask for support.

Asking for support is a sign of your commitment and determination.


When individuals who are successful in business and in life encounter a problematic situation, moment, or task, they know: Seeking the help of others always makes the moment more manageable.

Your friends and family will, of course, support you and share their opinions. While this support is precious and vital, it does not take the place of expert advice in the field most relevant to your needs.

Especially true if you are overwhelmed, stressed, or anxious; getting out of the state of “fight or flight” toward what you truly want may require the support of professionals. 

If you are facing a leadership challenge, career shift, or conflict, the advice is the same. Seek out the experts who can coach you to manage the moment and learn from it, while balancing and managing your priorities.

6. Dare to be different and make a difference.

If you do things well, do them better. Be daring, be first, be different, be just.

Anita Roddick

It is part of the human condition to want to be accepted and integrated into society. To this end, we often try to resemble the people in our closest environment. 

Consider the people, both famous and known by only you, who made their mark during their lifetime. They each have one thing in common: They were different. They brought a different perspective, idea, strategy, or way of being or thinking to the world.

Daring to be different means accepting that you are unique. No one is here, right now, with your set of intentions and your personal history, doing what you are doing. Instead of blending in, dare to be exactly who you are, and make the difference you are here to make. 

Becoming more daring takes practice and innate trust in yourself, in other people, and in your life. It takes consistency and repetition as you allow your curious and open mind to wonder what might be different about your life and what opportunities might come from your daring actions.

In the moment, being daring may seem scary, but as you practice this new way of being, you will realize that there is always something to gain from doing something just a little bit differently than you have done before.

Looking back at my own experience, it was always the moments when I pushed myself to dare and take new action that I grew the most, and which led to me being the person I am today.

These moments have been life-boosters, catalysts, and ultimately, the greatest learning experiences of my life. After all:

The greatest thing in the world is to know how to belong to oneself

Michel de Montaigne

As you consider what your next daring step will be, Point North International is here to be your guide. We bring experience and expertise to your career transition and look forward to supporting you as you boldly create the life of your dreams.

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