3 Questions to Help You Find More Freedom, Wherever You Are in Life
Learn how to manage mindsets that could hold you back from your dreams
As a career coach, I often work with clients who are feeling stuck — they can’t move forward, but they don’t want to stay still.
They may have an untested dream, steady side hustle, or budding passion, but haven’t decided to go all-in. They might be bored or burnt out.
They believe they can achieve more but are held back by the unknown.
They are caught in the tension between two different types of ‘freedom’:
- Autonomy: Working on the things you want, when you want
- Security: Feeling safe & not having to worry about meeting your needs
While the two are not mutually exclusive, it takes time to have them both.
Therefore, you need to figure out the right balance for you. This requires understanding your relationships with money, comfort, & acceptance — and identifying if you’re willing to change.
Pursuing freedom without addressing the mindsets holding you back will leave you spinning your wheels.
You’ll struggle to decide if there’s more freedom in certainty or adventure.
This was a critical lesson for me as I battled between guilt over not chasing my dreams and generalized anxiety that drove me toward stability.
However, through intentional reflection — outlined below — I was able to find an approach to freedom that works for me.
Now, I’m working towards my own goals, at my own pace, in my own way.
Because to understand what is really motivating and non-negotiable for you right now, you’ll need to dig a little deeper.
If you’re stuck between staying on your current course or jumping into something new, ask yourself the following questions to let go of constricting mindsets and feel more freedom:
What role does money play in your life?
Yes, we have to talk about money. It’s the biggest hang-up that I see from clients who have a strong desire to leave their job — which is reasonable.
We need it. How much of it? That depends on you.
We all have different relationships with money. Some see it as a motivating necessity, others a necessary evil, but for many — it’s a grey area.
Especially for those of us who don’t come from generational wealth, the idea of sacrificing any amount of stable income is not only terrifying but also completely contradictory to how we’ve historically lived our lives.
Money represents safety. It has never been a given.
So you’ve worked hard, and you finally feel secure in your finances. You can think about what you want to do — not just what you have to do.
But, you’re unsure if you want to sacrifice any of this newfound security.
Now, I will be the last person to tell anyone to quit their job without a plan to follow their dreams — it’s not what I’ve chosen to do.
Instead, if you’re feeling beholden to golden (or even brass) handcuffs, these steps can bring you closer to feelings of financial freedom:
- Define your lifestyle: Identify what is a need to have versus a nice to have. Be realistic about what you’re willing to sacrifice.
- Create a budget: Do the math to figure out how much you really need to provide for yourself & your family based on this lifestyle.
- Invest in yourself: Set separate savings goals to put towards personal & professional development. This could be courses, coaching, or even starting funds for your future business.
- Diversify your income: Time allowing, start your passion project on the side and put all the proceeds towards Bullet #3.
If you’re fortunate to be comfortable with your finances, but you still don’t feel free—money might not be the key that you thought it was.
Consider ways to manage your relationship with money, so that it doesn’t become the central decision-maker in your life.
Are you comfortable feeling uncomfortable?
There’s going to be a common theme here and it’s this: be honest with yourself about where you are now and where you are willing to go.
Growth comes with discomfort — fast growth comes with a lot of discomfort.
If you move quicker than you can stomach, you’ll likely burn out and give up. It’s hard to perform your best if you’re too far out of your comfort zone.
It’s also reasonable to enjoy feeling comfortable. After all, mastery is one of 3 core motivators (according to Daniel Pink) — it feels good to be good.
However, achieving mastery requires learning, growth, and — you guessed it — being uncomfortable.
If fear of failure, the presence of perfectionism, or discomfort with discomfort is holding you back, consider resources to move past these blocks:
- Try therapy (or coaching): Therapists & coaches are partners in shifting your mindset to move forward in life. If your aversion to discomfort stems from trauma or is very severe, therapy may be right for you. If it’s just an inconvenient barrier, a coach could be a good fit.
- Find mentors: Look to someone who is doing what you want to do, even if they’re also just starting out. If they’re further along than you, they can provide helpful insights and advice that calm your nerves.
- Lean on your support system: Tell people you trust about your goals & dreams. They’ll boost your confidence and help you turn anxiety into excitement. More importantly, I’ve found that by bringing others into the conversation, you end up inspiring them too.
- Go slow to go far: Go at your own speed. You don’t need to make giant changes or reach all your goals by tomorrow. Take small, enjoyable steps that keep the process fun and the dream dreamy.
Some people thrive off the thrill of diving in head first. Others prefer to wade in cautiously through the shallow end of the pool.
Neither is right nor wrong — the only mistake you can make is getting in too deep by yourself before you know how to swim.
So find a lifeguard and grab some water wings, but don’t stay dry just because you’re afraid to get your hair wet.
Are you willing to let go of societal expectations?
It’s impossible to feel free when trying to conform to external expectations.
Defining success on other people’s terms will almost always lead you to dead ends. Maybe not immediately, but eventually.
There are so many influencing voices and opinions in our lives — you’ll never be able to satisfy them all.
To find sustainable motivation, you need to figure out what really matters to you — not what you’ve been told is important to care about.
You can start in a few different places to tap back into what is intrinsically motivating, interesting, and exciting to you:
- Be a kid again: Think back to your childhood and what you loved to do — reading, writing, exploring, being outside, playing sports, drawing. Find a way to incorporate that hobby back into your life.
- Get curious about you: Reflect on your values, purpose, and strengths. Take assessments, ask your friends, use a coach. Get deep into who you are at your core, what brings you joy, and which superpowers you have.
- Dream big: Take time to let yourself imagine what you would do if you had no constraints — if time, money, and failure were not factors.
- Just start: Do something — anything — different. Take an improv class. Invite someone you admire to have a coffee. Put yourself out there in small ways to understand that failure only exists if you’re not learning.
If you don’t have your own authentic north star guiding you, you’ll likely cycle in & out of projects without ever following through.
It will take time, effort, and reflection to figure out why you want more freedom and what you’ll do with it, but it’s worth the investment.
You might just find that doing things that matter to you gives you more freedom than money, comfort, or acceptance alone ever could.
For more inspiration on how to live a values-aligned, purpose-driven life, follow Alex Stanton on Medium // @stantoncoaching on IG
