Small House Big World


Finding the Right Job

Anna Edgren • March 19, 2015

Before I delve into this subject, I would like to put a disclaimer here: I do not have some miracle solution for finding the right job. I am by no means an expert. If anything, the opposite is true:  I think I made some errors along the way in trying to choose a career, and I have learned a few important lessons that I would like to share in case they may help someone else. 

We will begin at the beginning: I have spent a long time not knowing what I want to do. So far it has been 30 years. Let’s pause here because something needs to be clarified. What does that question even mean? “What do you want to do?”

When I find myself presented with a question that stumps me, I begin to break the question into smaller parts to find out what is truly being asked. Often there are assumptions present in the original question. Without mentally addressing those assumptions, it is difficult to formulate an appropriate response. What do I want to do? I want to eat all the delicious food in the world while retaining my svelte figure, win 1 billion dollars in the lottery (go big or go home) and live happily forever after without a care in the world in a cozy log cabin in the mountains surrounded by family and friends and animals who love me. Right. 

This will do.

This will do.






So it turns out when people ask: What do you want to do? They don’t really mean that at all. They mean: What can you see yourself doing for a job that will make you enough money to support yourself? Which is a different question with a different answer. 

There are a lot of things to consider when choosing a profession. I decided the following criteria were important to me:

Criteria Explanation of Criteria
Subject Matter Something I’m interested in
Money/Compensation Something that pays well
Initial Monetary Cost How much does it cost to be trained to do this job? Can I make money in other ways while I’m training?
Initial Time Cost How long will my job training be? Weeks/months/years? Can I do other things while doing my training? For the right job it may take time, so this is flexible. There’s no fast lane to becoming a doctor, for example
Personal Strengths What am I good at? And perhaps more importantly, what am I abnormally good at? What do I succeed at where others fail?
Difficulty of Achieving Success How hard is it to succeed in my field of interest? Am I talented am I in my field? Is my opinion of my talents skewed? Am I giving myself too much or too little credit?
Daily Time Commitment How many hours a day do I want to work? Am I willing to work 10-12 hours a day or is 8 my max? Do I mind commuting? Consider work-life balance.

So how do these criteria apply to real life career choices? Which is the most important? How can I rank them? This is where things get tricky because all of these criteria are important in their own way. I will tell you how I ranked these in the past:

1. Money/Compensation – Crucial, the higher the better.
2. Initial Monetary Cost – Must be low.
3. Initial Time Cost – Must be low.
4. Difficulty of Achieving Success – Must be low. I don’t want to fail. I need as close to guaranteed success as I can get. 
5. Subject Matter – Mostly irrelevant. Preferably something I am interested in, but willing to discard this for the sake of money and ease of obtaining the job. I am interested in a lot of things, so I’m sure something will work out.
6. Personal Strengths – Mostly irrelevant. I can learn new skills and adapt to my new environment. I am a quick learner. 
7. Daily Time Commitment – Irrelevant. Everyone works a lot, and I should too. 

As you can see I put a lot of value in finding a job with high Money/Compensation, a low Initial Monetary Cost, and a low Initial Time Cost. In other words: I wanted a job that would pay well that I could obtain quickly and without any further training. To be frank, I didn’t just WANT one, I NEEDED one.  That is a situation a lot of people find themselves in. I NEED to be able to support myself, NOW. So those were my top 3. Unfortunately, focusing on only these 3 criteria is a great example of trying to solve a long-term problem with a short-term solution. 

Meanwhile, I let Difficulty of Achieving Success scare me. Many things went on the list of “too difficult.” This is a tough one, because on one hand, you need to be realistic. On the other hand, you need to figure out what you’re good at, and GO FOR IT. Some degree of chance-taking is simply required. It is a balancing act to figure out what is realistic for you given your talents and limitations. 

This is why it is important to adequately measure your Personal Strengths. In my case, I didn’t believe I was capable of achieving something difficult because I didn’t really know what my Personal Strengths were. 

specialI figured anyone could do the same things that I could do. I also figured I could learn to do anything that anyone else could do. This means I managed to simultaneously overestimate others’ abilities and overestimate my own abilities as well (impressive, I know.)  I couldn’t identify what I excelled at where others struggled. I didn’t know what I had that other people didn’t have.  Why would someone give ME that job when they could give it to 500 other applicants? I wasn’t sure. 

I also undervalued the importance of Subject Matter. I figured the things I was truly interested in didn’t make any money. Even in the rare cases where they did, it would be impossible to succeed because competition was so high. There is some truth to this. It is very important to realize that just because you love something, doesn’t mean you can make a living doing it. Some things ARE better as hobbies. However, that doesn’t mean you shouldn’t make an effort to find work doing something you care about in some capacity. There are lots of different avenues you can take within a specific field. Maybe you can’t make a living painting portraits, but you CAN make a living as a graphic designer. At least you’re in a similar field. In my job search, I essentially discarded Subject Matter entirely, which was a mistake. 


Finally, the least important factor to me was Daily Time Commitment. When you need money, you don’t much care how long you have to work for it. You are willing to do what it takes. I never gave Daily Time Commitment much thought, because I didn’t have the framework to do so. Pretty much everyone works 8 hours a day, so why should I expect anything different? 

So my priorities already seem a bit skewed, right? It seems obvious now, but hindsight is 20/20 of course. And the truth is, I would have been HAPPY to deal with a high Initial Monetary Cost and a high Initial Time Cost if I was passionate about something and could see a career path for myself where I felt I could be successful. But crucially, I did not:

I considered law school, but decided that the high Initial Monetary Cost and high Initial Time Cost were not worth it for something I didn’t feel truly passionate about. Furthermore, law school is hard work and the job market has been quite poor as of late, so Difficulty of Achieving Success was definitely a factor as well. I was also unsure if my Personal Strengths were up to par – I could read and write, but could I argue in front of other students and eventually a judge? I hate public speaking. So maybe not. 

I also considered becoming a philosophy professor, which also has a high Initial Monetary Cost and high Initial Time Cost.  In this case, the Subject Matter was the driver – philosophy is something I feel passionately about. Unfortunately, the Difficulty of Achieving Success is extremely high for philosophy professors. Becoming a philosophy professor is only slightly less difficult than becoming a rock-star, and you have to be a lot smarter. I have some amount of faith in my Personal Strengths in this arena, but I think that they are outweighed by the difficulty factor. 

Despite searching, I never found a career path that felt right to me. I never found anything that met my criteria. That is partially because my criteria were stringent, and it is partly because my priorities were off the mark. Therefore, I felt the path of least resistance would be most beneficial to me. I ended up taking jobs that were easiest – a job that would pay well that I could obtain without any further training. I had hopes that I would somehow just “fall into” the right career. You hear stories of this working all the time. Someone takes a random job out of college, and finds a way to make it work for them. They find their path and end up fantastically happy and successful. And this absolutely does happen!  It just doesn’t happen for everyone, and it didn’t happen for me. 

So before I knew it, I’d spent 10 years working in office jobs doing things I’m not really passionate about in industries I don’t particularly care about. Disappointing, sure, but I learned a lot in that time as well. I learned what my weaknesses are, and what I don’t want to spend my time doing. I also learned what I like doing, and what I’m good at. I tried to make the best of the situation I put myself in by spending as much time as I could focusing on the parts of my job that I found interesting. I spent time developing the skills I found to be important and useful, and tried to become proficient in those in order to create opportunities for myself in the future. Along the way I finally learned what my Personal Strengths are. This makes the Difficulty of Achieving Success less daunting. When you have some confidence in your abilities you are able to better remove the fear factor. 

But there’s more to it than that. I also made an effort to re-prioritize my values. It is so easy to focus on money as the solution to life’s problems. I want to be clear here that I am not trying to downplay the importance of money – being able to support yourself is critical and difficult, and is something that each person must try to figure out how to manage on their own terms. There can also be the complication of trying to support a family as well – in which case the stakes are even higher. This is a responsibility that is not to be taken lightly, and of course some sacrifices must be made. 

Even so, the overarching goal too often becomes “I must make more money” with little thought given to personal happiness and finding fulfilling work that you enjoy and are good at. It is assumed that money = personal happiness. Money will solve the problems. If you get money FIRST, the rest will fall into place. 

fancy kitty

In some ways, this is not entirely untrue.  Studies show that going from “barely scraping by” to “being able to comfortably put food on the table” provides a huge boost in life-happiness. But going from “being able to buy a decent car” vs. “being able to buy a Porsche” is a whole different scale. At some point, the happiness kind of levels out, yet you may remain tied to the idea: More money = more happiness. 

The desire for more is insatiable – it always creeps back.  More money means buying more things. Then you need to upgrade those things. “Sure my car works fine, but the Porsche is sexy!” Repeat process endlessly. It is easy for a person to find themselves tied to a house, a car, an entire lifestyle of consumption that they think will make them happier. Meanwhile, maintaining this lifestyle means being constantly busy, working to get even more – A slave to your possessions, and a slave to the way you make money.  No longer working to simply support yourself and your family, you are working to support the lifestyle. Too often that lifestyle ends up creating more problems than it’s worth. I saw myself going down that path and I didn’t like it. 

Again I would like to stress, what happened to me doesn’t happen to everyone. But I found myself unsatisfied. I found myself wanting more things, wanting more money, willing to sell my time and my interests in order to get more, and ending up unhappy because of it. The worst part was, I was beginning to lose sight of the things I cared about. I realized that I was trying to succeed at something I didn’t really want to succeed at. And why? Partly fear of failure, partly fear of taking risks, and partly indecision. And in the meantime, do I really need to spend $5,000 a year on clothing? How many hours did I have to work to be able to buy that clothing? Was it worth it? (More on that here.)  Imagine if instead that time was spent doing something I cared about that I found truly enjoyable and fulfilling?  Imagine if I saved my money to use only on things I actually needed? 

For human beings, time is a precious resource. Life goes by quickly. I find that there already isn’t enough time to do all of the things I want to do and see all of the things I want to see. So how depressing is it to come in on Monday morning and dread spending an entire week at my desk?

dog sadI wish the time would go faster so that it could be Friday and I could have my freedom back. It pains me that I have spent so much of my time wishing it away. And I’m not the only one. The way you spend your time should be valued and appreciated, it shouldn’t be something you have to suffer through 5 days a week. 

I decided that for me, it wasn’t worth selling 8 hours of my precious time, every day, for the cost of my happiness, my values, and my sanity. I needed to find ways to make money that weren’t slowly driving me crazy. I decided the way to do this first involved spending less money and focusing on living simply yet still comfortably. That would allow me to seek work that is more in line with my values. I needed to re-prioritize. 

I re-evaluated my career criteria, and decided that I had learned a lot since I last stopped to consider my options. I was able to restructure my criteria as such:

1. Personal Strengths – Very Important. Einstein probably wouldn’t have made a great professional athlete and John Madden probably wouldn’t have made a great physicist. Of course you can work to become better at things, but there is some level of innate interest and talent that needs to be identified and taken into consideration. 
2. Subject Matter – Important. Maybe I can’t make money doing EXACTLY what I’m most interested in doing, but I can at least get in the ballpark and work from there.  
3. Money/Compensation – Important. I need to be able to support myself comfortably, but I also need to remember that money is only ONE part of the puzzle here. Additionally, learning to live with less, spend less, and save more can at least take the edge off the driving need for money, reducing the desperation people feel about money. See this fantastic blog about rethinking what you spend money on
4. Difficulty of Achieving Success – Have the balls to take some chances. Taking risks is scary, and you should always have a back up plan in case things don’t work out. But that doesn’t mean you should avoid making big moves and trying for great things. You will never know what you can achieve until you try. Step 1 = Try. Step 2 = Try again. Failure is a part of the process.
5. Daily Time Commitment – Work/life balance is important to consider. If you don’t take care to ensure you have enough time to spend with people you care about, doing things that you care about, you will burn out eventually in one way or another. 
6. Initial Monetary Cost – Preferably low but should not be seen as an impenetrable barrier.
7. Initial Time Cost – Preferably low but should not be seen as an impenetrable barrier.

So how do I make this work? How do I restructure my career to allow these priorities to come to life? For me, the answer was a bit “outside of the box”.  My boyfriend and I decided to buy an inexpensive RV with cash, I had to quit my 9-5 stationary job, and I am in the process of coming up with mobile/remote ways to make a living. Drastic? Yes. So why on earth did I decide to do this? 

1. I’ve lived in Chicago for 7 years – it’s time for something new.
2. I was dissatisfied with my job, talked to them about it, and unfortunately we couldn’t work it out, so I quit. I have spent the past few years developing valuable skills that I hope will help me find interesting remote work. 
3. I love to travel and I love to drive. 
4. I was interested in a work schedule that isn’t 8 specific hours a day. I’m also interested in value being placed on the results I produce rather than the time I am able to spend in a seat. 
5. I discovered that the things I like doing most can be done remotely: Reading, writing, editing, information management, excel, and programming.  If I have a computer, I can make it work. 
6. I want to focus on doing the things I like to do most. There are ways to monetize my talents in these areas above, and I will find them. 
7. I want to pare down my possessions. Limiting myself to only the items that can fit in a 300 square foot RV is a fun challenge.  And I can make some extra cash selling the things I don’t need anymore. I can also focus on not spending money on things I don’t need. The mental space that this frees up is exhilarating. 

This concludes my story for now! Maybe this will end up being a colossal failure – who knows. I’m just excited to finally take some chances. No more taking the easy way out. Time to find out what happens when you cut the cord. In my search for inspiration, I came across a quote that I find to be appropriate here: “You throw yourself off a cliff and assemble an airplane on the way down.” – Reid Hoffman, co-founder of LinkedIn. 

Here we go!

kitty flies

career advicefinding the right jobjob advice

Anna Edgren • March 19, 2015

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  1. Natalie July 15, 2015 - 11:26 am Reply

    Hi Anna! Thank you so much for sharing your story. I hear you on so much of this, especially on fearing failure. I think my priorities have also shifted a lot, in ways I did not anticipate. Working in a field where I could convince myself that I was making a positive impact, while still making money, was my initial career priority. So, I wound up in government. Now that I’m here, I find myself constantly hatching escape plans. Perhaps personal freedom doesn’t rank high in the priorities early on because, as a college student, we have more personal freedom than most people have in the rest of their lives…

    • Anna Edgren July 15, 2015 - 11:40 am Reply

      Hi Natalie – Great point on the perspective of a college student. It is always hard (impossible??) to see around the corner and predict how different surroundings will change your views. I have been thinking a lot more about this topic lately as I recently started working full-time for a company that is 100% remote. I have found the whole experience super interesting and I am going to be publishing a post about that here shortly!

      • Natalie July 15, 2015 - 1:04 pm Reply

        Congrats! Looking forward to it!

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