Not fulfilled in a job, but haven’t been able to make a move? Always wanted to chase a certain dream but haven’t found the right time to start?

While there are many ‘real-world’ constraints we must deal with, we also impose more limitations on ourselves than we often realize. Separating these helps us get a better sense of what our real options are and can help us get more fulfillment.

I was fortunate enough to speak with Jeanne Hwang on how to break down these internal barriers. Jeanne first became famous by applying to Pinterest on Pinterest.  A Harvard graduate who’s worked at Yahoo and Accenture, Jeanne currently leads Wattpad, a storytelling company based in Canada, as General Manager.

She’s also participated in multiple leadership conferences and organizations for women and focuses on building a culture of support for people to thrive in.

This article takes her approach to finding and breaking free from the constrains we place on ourselves to find more fulfillment.

 

Chasing Fulfillment

While finding more fulfillment is different for everyone, there are a few things we need to overcome:

• Making decisions out of fear
• Mindlessly falling into social pressure
• Lying to ourselves

Naturally, the process of finding more fulfillment is different for everyone as well. Below is a diagram highlighting a high-level roadmap:

Let's explore.

 

Authentic Reflection

To start, we need to work on becoming systematically more honest with ourselves.

We want to discover the foundation of our decisions, how we act, and our desires.

Examine how you made past decisions and what drove you to them. Be being brutally honest, but non-judgmental. We aren’t pointing fingers, we’re learning.

Start by asking questions: Why did I make this decision? What did/didn’t I like about this? What external factors played a role in this? What other factors impacted me? Did I get what I wanted? Why or why not? These are the same types of questions you’ll ask yourself for future decisions as well.

Ask “why” to each answer of these questions to go deeper. Using an approach similar to the Kaizen’s Continuous Improvement, ask “why” 5 times.

What was the root of your decision? Did you make your decision for the reasons you claimed or thought? Was there fear driving your decision? What external factors impacted you? Knowing about past decisions helps you make better decisions.

A final component for reflection is to seek out feedback from trusted friends and mentors. External guidance on your capabilities and goals can give you a fresh perspective, a reality check, and new knowledge.

 

Chase authentic reflection and use past decisions to make better decisions in the future.

 

Decision Making

Before picking a path, ensure you understand how it relates to becoming a better version of you. Will this improve you? How? Remember, this is a continuous conversation with your authentic reflection.

Once you have a feeling for the direction you want to go and what’s best for you, you need to explore the decision, follow through, and implement it.

Start by addressing your root concerns. Ask yourself questions to understand what worries you about implementing this decision.

Use the techniques in Authentic Reflection and ask “why” 5 times to ensure fear or frustration isn’t secretly the root driver of your decisions. This is especially important to understand when you decide not to change.

 

Fear and frustration always move us away from our best selves and can be major internal barriers.

 

Psychological Safety

Creating Psychological Safety will give you confidence in executing and sticking to your decision to improve. This is needed to help you through the rough patches of change, especially if the needed improvement is new or initially scares us.

List out all of your concerns from before. These are usually very practical.

Some examples: “do I have the right skills”, “how can I build the experience I need”, “what will my friends and family think”, “what if I don’t have the financial stability”, “how long will this take to change”.

Which of them are based on your environment or situation and will take a while to change?

Being afraid or worried about these is natural, so develop ways to mitigate and overcome what you can control to ensure they don’t prevent you from improving yourself.

Tackle each concern as honestly as possible:

• How likely is this to happen?
• What can I do to prevent this or prepare for this? What resources are available?
• What’s the worst possible outcome?
• What would I do if this happens?
• How can I mitigate this?
• Can I still be happy even if the worst-case scenario happens?
• How confident am I that I can execute what I need to with the situation’s constraints (time, money, etc.)?
• What are my backup plans if this fails? What are my realistic options from there?
• Am I okay with this risk? Is it better than not doing anything? 
• What are opportunities do I have to grow from this? What can I learn?

Answer specifically. Use these answers to create psychological safety, risk mitigation, and back up plans. Don’t let fear or other emotions hold you back from making a decision to better yourself. What are the biggest barriers?

This will prepare you to execute your plan and flesh out what you need for it.

 

By going back to your authentic reflection, you’ll know you’re making the best decisions for your future. Create psychological safety to stick to them.

Finally, trust your gut. After you’re sure you’re not making a decision out of fear, you may still have several options. Awesome! In this case, use your intuition and go with what feels right.

Making good decisions is always built off of a continual conversation with your authentic reflection. Ensuring you have psychological safety enables you to follow through on what’s best for you. Both are needed to become your best self.

 

You’ve only got one life – make it your best.

 

HUGE shout out and thank you to Jeanne. We worked together on this article for well over a month and in the process learned a ton, created and challenged our ideas and beliefs, and formalized techniques she’s used and developed throughout her impressive career.