The 5 Stages to Career Fulfillment in Your Twenties

Have you ever felt anxious about not having your life “together” and blamed yourself for not having it figured all out?

It’s a common tendency that we have. And on top of that: just when we feel like we’ve made some progress, the confusion comes back again. It’s like a never ending cycle.

What if I told you that rather than an inexplicable mystery, there’s actually a process to getting clear on your dream career? AND with each exploration step that you take, you’re actually getting closer instead of going around in circles?

Having your career “figured out” isn’t a result, it’s a process.

And from working with a variety of clients in my Get Unstuck program for the last 2 years, I’ve noticed a pattern that’ll help you navigate it: it’s the 5 stages to career fulfillment in your twenties. 

Similar to picking up a new skill and going from novice to expert, each stage comes with different challenges and resources required. The purpose of this article is to be the guiding hand that’ll get you from where you are, to where you want to be. Below, are descriptions of each stage, reflection questions and resources to help you easefully level up to achieve career fulfillment.

First, I'd like to invite you to think about the process like this:

You are now standing on the opposite side of your career dreams. Separating you, is a stream. Each career stage is a stepping stone that’ll help you get closer as you figure it out more. The exact point of your destination will change depending on your discoveries and learnings during each stepping stone.

Stage 1: The Stagnation 

It’s been 2–3 years since you’ve gotten your dream job at a tech company or a stable company like the Big 4. And now you’re wondering if you actually got the job because you wanted to, or because your parents wanted you to. 

The main challenge here is that you’re feeling bored. According to society, you should feel fulfilled. But you don’t. Because your work feels uninteresting and meaningless. On top of that, you feel burnt out and under appreciated. You may be wondering: “Is this all there is to life?” and “Is this what I worked so hard for?”

Pro tip: Instead of looking for external validations like salary and status, try looking within to see what’s truly important to you. 

Reflection questions: 

• If you went after a career that felt 100% authentic to you, what would that be? 
• What type of work would feel interesting to you?
• What are your values, especially your workviews? 

Resource: Linchpin by Seth Godin

Stage 2: The Identity Crisis

As we realize how different our values are from our current work, we start to second-guess ourselves. This is also a result of putting ourselves in a career box that others have made. 

The main challenge here is that you’re feeling lost. A previous client said it best: “After I started working in corporate, I felt like all my interests went down the drain, and I didn’t know who I was anymore.”

Pro Tip: To get past this stage, it’s helpful to get clear on your innate interests and strengths. 

Reflection questions:

• When am I at my best, what activities am I doing?
• What’s my North Star in life?
• What type of person do I want to become in 5 years? 10 years?

Resource: The Defining Decade by Meg Jay

Stage 3: The Exploration Rollercoaster

The more clear you get on that your current reality isn’t where you want to be, the more it’ll drive you to action. Maybe you find yourself picking up a new creative hobby or starting a blog. These are often known as side projects or passion projects. 

The main challenge here is you’re prone to be on the extremes of ups and downs. Doing something new is exciting, so at first you’ll get an all-time high. If you go all in too fast, you could experience burnt-out. Learning something new is also hard, so you may feel dejected and generalize it for your life.

Pro Tip: Beware of the distraction trap. When you find yourself busy with an activity, ask yourself if it’s to avoid reality (i.e. Korean dramas if you’re like me), or to explore reality (i.e. photography class).

Reflection questions:

• If you had all the time in the world, what would you want to spend it on?
• What activities usually feel energizing for you?
• What project would you be excited to try out for 30 days? 

Resource: How to Start Your Own Side Project (from yours truly;)

Stage 4: The Serious Contemplation

Now that you’ve explored what else is out there, and have felt how it’s like to work on something you love, you’re seriously considering changing careers where you could feel that way every day. 

The main challenge here is that you’re unsure if you could make it happen. You may be second-guessing yourself if it’s actually what you really want to do, and imagining all the worst case scenarios if you fail to get another job.

Pro Tip: It’s easy to overthink and try to figure it out in your head, which doesn’t work. Try prototyping or getting a taste of how the career’s day to day would look like to see if it’s actually a good fit for you.

Reflection questions:

• If you don’t take this step, will you regret it? What would the 80 year old you say to yourself?
• What actually feels like a waste of time: staying in a role you already know it’s not the right fit for you, or trying out something to see if it’ll be a better fit? 
• What would be the worst case scenario if you made a career change? And the best case scenario? 

Resource: Designing Your Life by Bill Burnett & Dave Evans

Stage 5: The Career Change Commitment 

Congratulations, you’ve decided to change your career, and in turn your life!

The main challenge here is you’re unclear about the next step. You can have the intention of changing careers, but if you don’t have a plan translating it into actions, then you’ll stay stuck.

Pro Tip: Get clear on what’s keeping you stuck: Is it lack of confidence? Lack of motivation? Lack of discipline? Then find resources that’ll get you past it — because you’re so close to setting your new career into action. Don’t give up now! 

Reflection questions:

• How urgent is this career change? Is it in the next year? 6 months?
• What type of career change do you want to make: is it switching into a different role? Industry? Lifestyle (not the traditional 9–5)?
• What would help you get there the easiest and fastest: is it getting an trusty accountability buddy? A mentor whom you want to be like? A coach who specializes in career change? 

Resource: If you’re 100% ready for change and would like someone to take you through your career change step by step, my Get Unstuck program is now open for the August Cohort ??????.

Just like this article, I’ll be your guide and will lead you through each stepping stone, getting clear on your vision to creating your experiential project so that by the end of the month-long program, you’ll know exactly what the next fulfilling career is, and how to get there.

All you have to do is show up as you are.

Everything else will be taken care of for you :)

Previous clients have been able to easefully switch to creative careers: from engineering to coaching, marketing analytics to recruiting, and much more. If you also want a fulfilling career for yourself, come join us in the Get Unstuck program (we start on August 1st)! 

Hope to see you on the inside, and know that you absolutely deserve a career you love.

?? If you know someone who would benefit from this article, please tag them below or share this with them! It could be exactly the encouragement they need. Thanks friend ??.