Are You Looking for More Meaningful Work?

Take Charge of Your Career, Job Search

In a recent post I wrote called How To Know If You’re On The Right Career Path.. Or Not, I asked you to see if any of these 5 red flags resonated with you:


1. If you're not happy with your job, but don't know what to do instead

2. If you have a hard time waking up for work in the morning, or dread going into work every day and feel like it's just a waste of time

3. If your company doesn't seem to appreciate all that you do for them and there's little opportunity for growth

4. You've been thinking about quitting for a while now but haven't done anything yet because of fear or uncertainty

5. Your friends and family are constantly asking if everything is okay at work and why you aren't satisfied with what you're doing anymore


What did you do after reading that? 


Were you like, “Holy freakin crap, Ryan! You are describing my life!” Then you quit your job and started putting all your waking hours into job searching?


I’m all about getting yourself out of a draining or bad situation, but I’m also about strategy. 


The strategy doesn’t have to be perfect to be effective either. 


A conversation that I don’t know if anyone ever had with you, that I’m kinda (umm, a bit more than kinda) pissed off at society for not doing with our kids, especially as they grow up and try to pick jobs and careers,  is asking people if they are actually doing value-driven work. 


If what they are choosing to do for work--so many friggin’ hours of their waking life--actually aligns with or supports what they really care about in some way--directly or indirectly.


What do I mean by value-driven work


This is my definition:


Making sure that what you are doing every day supports and aligns with what truly matters to you. If creativity is something you value, but you are stuck behind spreadsheets (which can have creativity!) but you are adding numbers all day--your work life (which boils over to your life-life) is probably gonna suck!


If you value family, but you never see them because your job is so demanding that you work crazy long hours, you ain't gonna feel so great about your situation. 


Here is the thing about defining your values... 


They are the beliefs you hold about what equals a good life to YOU. No one else can tell you that.


What I find frustrating about most exercises that are designed or meant to help people identify their values, they don’t take into account life experience, and how our internal impulses and instincts actually tell us what we value and don’t value ALL THE TIME. Sadly, if we’ve been dissatisfied for a long time, we suppress that, but nonetheless, our insides are still sending the messages--just reread that above list of 5 things…


Ok, here is the real way you need to go about finding your values so you can make sure you are not on an endless hamster wheel of spinning around at the same thing that is leaving you feeling some level of hollowness.


Ask yourself these questions:


On the movie screen of my life--what have been some of the climaxes/highlights? 


Get specific, what experiences left you feeling super pumped, happy, proud, satisfied, fulfilled, or energized? (These could be recent or experiences that happened years ago.) Think about this in all aspects of your life (things you’ve done at work, school, and in your personal life). The experiences don’t have to be big or grandiose either.


  • Was there a specific need or desire that was being met?


Once you’ve written a few experiences down, take a look at them and write what values you were honoring in each experience. (If you aren’t familiar with values, it is okay to look at a list to pick the right words, but remember that you are the only one who knows what the right word is. Here is an example of some common values.)

Next, I want you to do the opposite…

When were some of the times you got really angry, felt frustrated, drained, or like you really didn’t want to do something?


Write down about those experiences and why you felt that way. 


  • What need or desire was being neglected or pushed aside?

Now identify what value was being dishonored or suppressed.


Scott Jeffrey is a coach that does an activity similar to this with his clients, only he takes it further with more steps that help you reduce down your values to 5-10 core ones (this makes things more actionable and brings a lot of clarity for making decisions about work and life). I HIGHLY encourage you to do his ENTIRE 7 Steps to Discovering Your Personal Values.


Knowing your core values will empower you to make the right choices about what job to take next, as well as setting actionable value-driven goals for the changes that need to be made--to do more meaningful work, and find more satisfaction and fulfillment in your everyday life. Once you know your core values…


Define what success means TO YOU.

When we are young, we get an idea from our parents, teachers, friends, society, the media, and other sources about what it looks like or means to be successful. 


They wrote a script for us.


Maybe that script was to pick a really secure line of work. Maybe that script was to make a certain amount of money every year. Maybe that script was driving the nicest car and living in the biggest house in your neighborhood.


Ridiculous that most of us don’t actually get asked to define what success means for us or what it looks like in a job. What you value (and don’t value) helps you solidify what a successful life looks like for you. 


Go ahead and take a minute to write down your best definition of what it means to you to be successful in work and in life. 


Note: you don’t need to hold back when you do this. It will not be graded.

Places to start:


  1. How much money do you want or need to make to live your definition of a good life?
  2. What lifestyle do you want to sustain?
  3. What kind of work/life balance do you want/need from a career? 
  4. What kind of people do you want to work with and for?
  5. What type of tasks would make you happiest to work on?
  6. What kind of subject matter would make you happiest to focus your energy on?
  7. What kind of benefits package and time off do you want?
  8. What kind of work environment would you thrive in?

There is power in taking the time to do this.  I’ll share with you a small example (your life will be a bigger example!) but back in middle school, for some class, we were asked to write about our future careers. I was pretty out of touch with what I wanted to do with my life (how many teenagers REALLY know?). The only thing I remember writing down was how flexible of a schedule I wanted. I got pretty specific--I wrote what times of day I did and didn’t want to have to work and that I wanted Fridays off. 

Funny thing is, I forgot about that “list” of criteria until something recently triggered the memory. I realize looking at my adult working life now, that I brought that list into reality. Sure, I actually really like working as an adult (because I found what I can define as meaningful work for myself). But honestly, if I really still wanted Fridays off like my teenage self--I could make that happen.


It is important to recognize what kind of mental noise is affecting our career decisions.

Sharon Belden Castonguay (a career counselor) gave a Tedx Talk about  The Psychology of Career Decisions. She spoke about how the scripts that others write for us about our careers need to be examined. She said that “a script is deeply personal, but we also must learn not to just follow it to the letter. We must learn to understand it and question it. Your script is iterative and like any writing process, it’s likely to be messy. I urge you to embrace that messiness. Own your story and don’t let others write it for you, and know that this process has always been messy.”


She goes on to say, “I submit to you that most people do not make career decisions rationally but rather based on deeply-held often unconscious biases that they received from their social surroundings. They’re highly influenced by their parents, their peers, their local communities, and they internalize a lot of these biases that they see around them and they...also tend to internalize messages that they are receiving from their local and national cultures particularly around personal identities like gender, race, religion, or socioeconomic status, and will tend to either embrace or foreclose on options accordingly.

“Particularly if they anticipate barriers for success. And let’s acknowledge that a lot of people do face barriers to success particularly along the lines of gender, race, religion, socioeconomic status, sexual orientation, but this is exactly why I think self-awareness is so important because [it] us not internalize these biases that are coming from culture.”

I hope that you and EVERYONE can stop listening to the scripts that make us feel like we can’t have the kind of success we want!!!!


If you are feeling brave...try this


Milton Glaser, a famous graphic designer, did an exercise with a class some years ago where he told the group “to envision the life that they could have if they pursued everything that they wanted, with certainty that they would succeed.


In this “Five-Year Plan”, the students were assigned to:


  • Dream big
  • Not edit themselves
  • Be careful what they wished for (because it might just come true…)” [*]

Here is an adaptation of this exercise:

My Life: Five Years From Now 

Take out a piece of paper and write out what an entire day of your ideal life looks like, five years from now (the minute you wake up, including who is next to you, all the way to going to sleep at night). 


This is your ideal life. This is what your life looks like if you let yourself dream big. If five years sounds too soon, do it 10 years out.


This exercise will help reveal exactly what you value and what success means to you. 


What do you do with this information??


Use the information these exercises uncover to help yourself start getting the necessary skills to move away from what isn’t fulfilling you--and to find a job that is meaningful FOR YOU. That transition can be made at any pace you need for your circumstances. 


Years ago I read the book called “Well-Being,” by Tom Rath and Jim Harter. They are part of Gallup and a study that spanned 150 countries. They discovered what makes people's lives thrive. 


They said there were five core elements that people need to work on to have a meaningful and thriving life: Career Well-Being, Social Well-Being, Financial Well-Being, Physical Well-Being and Community Well-Being. They define Career Well-Being as “how you occupy your time or simply liking what you do every day.”


I’ll never forget one important discovery they made: if you don’t like the work you are doing, you need to do everything in your power to make sure you are not doing it more than 20 hours a week--or it will adversely affect your overall well-being. They also found out that if you improve one aspect of your well-being, it has the power to help you increase all other aspects of your well-being.


Start “leveling up” your career! Be willing to expand your job search criteria!


If you’ve been limiting yourself to one industry or type of work, start expanding yourself out. Check out online certificates that are very affordable and don’t require going back to school (debt + time) for a degree. I really like UdemyHubspot Academy, and W3Schools. You can learn things like web design, digital marketing, project management, how to start a business, graphic design, programming, and hundreds of other marketable and transferable skill sets.


These skills can prepare you to do things like switch industries, start your own business, get remote work, and make a transition to a better position that you actually find fulfilling!

Self-knowledge is incredibly powerful and the only true way to get yourself on the right path and in the right job--doing meaningful work--whatever that looks like for you

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Ryan Kay

Helping people get the career of their dreams!

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