Confident Decision Making: How to Stop “Winging It”

Confident decision making is a skill. Like any other skill, you can improve with time and practice.

But it only works if you practice effectively.

Your future is not a piñata. Taking random swings at life won’t get you anywhere. To make confident decisions, you need clarity and a plan. You need to act intentionally.

Let me explain—

Imagine you’re at a children’s birthday party. There’s a young child with a blindfold and a bat and an adult who spins them around and gets them nice and dizzy before they take a swing at a donkey, unicorn, or star covered in stringy green, red, orange, yellow, and purple crepe paper.

When they swing, they’re unsteady on their feet. They literally can’t see. Some children will even bat wildly at the air, missing the piñata altogether.

So many of us approach life like a child trying to whack a piñata. Our paths look just as meandering and crazy. There’s no logic. We take random chances and hope for the best. Why does this happen?

The Heavy Weight of Others’ Expectations

When we’re in our 40s and 50s, we’re so blinded by others’ expectations—by others’ perceptions of us and what we think we should be doing—confident decision-making feels all but impossible.

Whether we want to uplevel our skills, ask for a promotion, make a career shift, or have more flexibility in our schedule, we lack direction and a plan.

In fact, most people don’t even know what they want. They know they would like to make a shift but don’t know what to do next. They don’t even know where to begin.

I highly recommend starting with my Career Audit.

After years of talking to clients in the early stages of change, I’ve developed a tool to help you assess where you are right now and get a clear picture of where you want to go. When you complete the Career Audit, you’ll have a roadmap from point A to point B.

To get a detailed career blueprint, the assessment looks at five areas—mindset, motivation, mission, mechanics, and momentum. Here’s what to expect.


First things first, are you on the right career path? How do you feel about your life and career without changing anything? The first section of the Career Audit focuses on mindset.

I see it all the time. Clients come to me looking for an easy button. They feel restless, uncomfortable, or unhappy, and they think the fastest and most effective way to feel better is to swap careers. The truth is a new job or career might help, but it might not.

Take Elizabeth…

When I began working with Elizabeth, she confessed she used to love her job, but, over time, she began to feel less and less fulfilled. It didn’t make sense. Her position hadn’t changed. Elizabeth decided she needed to make a career shift. She believed she would feel more fulfilled elsewhere.

As with all my clients, I asked Elizabeth to complete the Career Audit. When we looked at it together, Elizabeth indicated that her boss and teammates celebrated and included her, she contributed often, and she felt grateful for her role.

In other words, the problem didn’t seem to be her job. After digging deeper, we discovered she didn’t feel accomplished or joyful on a more personal level.

Elizabeth worked long hours, and when she got home at the end of a long day, she sat on the couch and binged Netflix. As she crept closer to retirement age, not having a hobby or treasured pastime outside of work weighed more heavily on her. She began to feel like her job defined her and grew to resent it.

When I asked Elizabeth to explore hobbies and relationships and reconnect with the things that used to light her up, she began to love her career again.

The Career Audit and its questions about mindset, in particular, helped Elizabeth gain clarity. After completing the audit, she realized her work hadn’t changed. Her circumstances at home changed.

With insights from the Career Audit, Elizabeth could engage in confident decision-making and find more meaning when she wasn’t working.


I’ve helped many women discover who they are what work suits them best, and ultimately land their dream roles. My goal is to help you find a clear path forward. As Brene Brown says, “Clear is kind; unclear is unkind.” To gain clarity, we have to look at our motivations.

The second section of the Career Audit is all about motivation. Think about crossing the street. Before crossing the road, you look both ways. You gather data. You don’t just mindlessly step off the curb.

Transparent, kind, and confident decision-making starts with gathering data, and our motivations are data.

Consider: Does your current career inspire you? Is it a good culture fit?

Ask if your peers and boss respect you and cheer you on. Get honest about the energy you feel at work and whether that energy fulfills you and encourages you to grow. You know it’s time for radical change or a career shift when your energy is low and you feel trapped in a low-energy state.


Confident decision-making starts with identifying your values and determining if they align with your company.

For example, many professionals value growth. Their mission is to keep setting goals and achieving them. They want to aim higher, work on themselves, and make tangible progress year after year. The third section of the Career Audit centers around mission.

To find out if your role is a good fit, ask questions. What do you know about your company’s mission and values? Know whether there’s room to grow, what to expect regarding performance reviews, salary increases, and bonuses, and whether they set weekly, quarterly, and yearly measurable goals.

Recently, I had the pleasure of working with Michelle. Michelle was a high achiever who didn’t know what to do after a reorg. Before the reorg, Michelle’s company outlined a clear path for her to move up and continue to grow with her company. The reorg eliminated several vital roles, including positions Michelle planned to enter one day.

Her way forward was unclear. Under the new system, she had reached the top rung, and there wasn’t anywhere left to go.

Michelle knew she was unhappy with her involuntary career shift but didn’t have words for it. She didn’t know how to describe what she needed from her next role. The Career Audit helped her see that it was growth and a mission that lined up with her employer’s.

Armed with that knowledge, we gathered data, moved on to confident decision-making, and helped Michelle find a more fitting role.


When it comes to career shifts, I take a holistic approach. Confident decision-making and designing your dream life comes from understanding who you are, why you do what you do, and getting the details or mechanics in order.

In other words, to ace the job interview, you need an optimized LinkedIn profile, a solid network, and an up-to-date resume.

The fourth section of the Career Audit focuses on these foundational pieces. In this section, you’ll find helpful questions to get you started, and it’s a great list to return to before your next big interview.


The final section of the Career Audit explores momentum. Overworking, poor work-life balance, and burnout all risk derailing your momentum and leaving you feeling exhausted and overwhelmed—or even at a standstill.

This section of the Career Audit helps you see the bigger picture. I’ll ask you to reflect on your work environment, level of engagement at work, the meaning you find in your job and your contribution.

So many of my clients want to feel like they’re making a difference or fulfilled at work. When we review this section, we’ll talk about the purpose and joy people find in philanthropy and whether you’re comfortable finding it directly or indirectly.

For example, dozens of people I talk to think they would feel fulfillment working for a nonprofit. After some digging, we often find that joining the company’s team for a walk that supports cancer research and helping their company organize more events to give back to the community can scratch the same itch.

Confident decision-making starts with a roadmap

The Career Audit gives you clarity, direction, and a plan. Think of the sections—mindset, motivation, mission, mechanics, and momentum—like the most prominent landmarks on a map. These are like the mountains, rivers, valleys, and interstates. When you check or don’t check individual items off the list, this helps you fill in the finer details. These become your parks, streets, airports, and towns.

Once the audit is complete, we discuss what sections stand out the most. What appears most important to them? And what areas feel complete. We also uncover what still needs additional work.

With that clear picture, we’re able to ask what’s next. We have enough data to engage in confident decision-making and determine whether you need to find more joy in your personal life, reconnect with what brings you meaning at work, or make a more significant career shift from one field to another.

The Career Audit converts the thoughts my clients knock around in their heads every day into actual, tangible data we can use to inform their journey. If a career shift or any other significant change is in your future, you don’t have to go into it blind. You shouldn’t. Take the Career Audit to clarify your thoughts and the subsequent proper steps. I’d love to review your results in detail. Schedule a free one-on-one clarity consult to unpack what you need to have a confident decision-making plan for your career.

Free Career Clarity Consult

There’s nothing more confusing than trying to figure out what you were meant to do with your life, especially when you’re trying to do it all alone. Now’s your chance to talk with an expert about your career free of charge.

With my complimentary career clarity consult, you’ll have the opportunity to have your career questions answered as well as learn some of the best strategies to winning in the career game from someone who’s been in your shoes. We’ll cover what you want to achieve and point you in the proper direction if you are feeling stuck and unsure what to do. Because I hold these complimentary calls personally, space is limited. Click below to apply.

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