Last Updated on May 18, 2021
Society makes it seem like getting a job is an easy and straight-forward process. You go to school, get a job, and spend the next 40-50 years working your way up within the company before you retire.
The reality for most of us, however, is much different.
Finding a good job is a struggle, let alone finding the career path that is right for us. Especially when most of us picked that career path as an inexperienced high school student.
A lot can change as we grow and start experiencing more of the world. How we picture our lives as a teenager is rarely the same thing that we want as we get older.
And in many cases, the world has other plans for us, anyway.
“Success is not a straight line, it’s much more of a dance and being open to possibilities.” — Arianna Huffington
So if your career path looks more like a winding road full of twists and turns than it does a straight line – don’t worry!
I asked other professionals to share their stories of how they got hired. And you will quickly see that everyone’s path is unique.
Table of Contents
Amanda Kay of My Life, I Guess
My career path has had a lot of detours, which ironically is how I ended up becoming an Employment Specialist. I landed what I thought was my “dream job” as an Arts Educator before graduating, but quickly found myself working 60+ hours a week for an abusive boss (and very low pay). After a year of unsuccessfully trying to find a new job, I ultimately ended up taking a stress leave instead. That was over a decade ago.
Since then, I’ve worked 11 different jobs ranging from working with children to working with inmates at a maximum-security jail. Between being unemployed, under-employed, laid off, and even wrongfully fired, I’ve essentially spent over 10 years job searching. I didn’t consider that applying for all of these positions was teaching me the skills and experience I’d need to qualify for one.
I now work at an employment center, where my job is to help other people find jobs! I get paid to look at job boards, edit resumes, and give unemployed and under-employed people the same advice and encouragement that I was recently getting myself. This job is perfect for me but is not something I ever would have considered had it not been for the detours that led me here.
Elementary Special Education Teacher
Tawnya Redding of Money Saved is Money Earned
I had an interesting path to my job as a teacher. Originally I wanted to be a psychologist but I graduated during the recession and found myself unable to get into grad school.
I began working at a treatment facility and found that the thing that seemed to make the biggest impact was the teaching. I ended up going back to school to get my Master’s in Special Education and I’ve been working diligently to maximize the benefits of a teaching career since. I’ll be heading into my 8th year this fall.
Senior Financial Analyst (Retired)
Sebastian Rodrigues of Money Saved is Money Earned
I have been retired for 7 years. I emigrated from India when I was 22 years old, and with just $15 in my pocket.
At first, I had to take any job I could get. I cleaned the Portland State University cafeteria after hours while attending college there, and also had a summer job with the Portland Parks and Recreation as a maintenance laborer. I experienced a lot of adversity but finally landed a position in the finance department, and 30 years later I am an early retired Senior Financial Analyst for the City of Portland.
Head of Marketing
Todd Kunsman of Invested Wallet
Back in 2014, I was laid off a few weeks before Christmas and around that time I was trying to find direction for my career. I felt stuck, but noticed that I was enjoying aspects of digital marketing. I went to college for computer science and had a minor in communications, which is not exactly in the field I now started to love. However, I knew digital marketing jobs were ways I could make money online and there was also demand for this career with great earning potential.
With digital marketing, you don’t necessarily need to go back to school to learn and get hired. Instead, I built a music blog to teach myself some basics. In my previous job, I was doing some email marketing, and I dove into any free certifications online like those from Google and HubSpot. However, after researching digital marketing further it appeared to me that working for a marketing agency would get me the most experience and I could learn quite a bit. So from 2015 until 2017, that’s exactly what I did. I learned from co-workers, plus got to work with many start-ups and well-known brands.
My other goal for my career was to work full-time remotely. Once I gained some experience from the marketing agency and continued to learn, I applied to software companies that hired remotely. I actually emailed the CEO of the company I work for now directly in 2017 and have been with them ever since.
Special Education Teacher
Josh Hastings of Moneylifewax.com
Becoming a teacher was something I decided I was going to do when I was 14. During my freshman year of high school, I had a very impactful physical education teacher who showed a lot of interest in me and was always motivating. From that point forward I made the right moves to graduate eight years later with my teaching degree in Physical Education/Health Education.
However, like many graduates in 2009, getting a job was few and far between. After only landing one interview, as the saying goes, “It’s all about who you know,” a classmate’s mom reached out to me right before I was set to enroll in graduate school to let me know there was a job opening at her school. Knowing a Master’s degree in a different field of education would make me more desirable, I had actually taken a prerequisite to obtain my certificate to also teach special education. This coupled with the job opening got my foot in the door as a teacher. Fast forward 11 years, and I still love my title – History Resource Teacher – and I love teaching life skills in addition to history!
While it wasn’t the exact path I was going after when it came to teaching, had I not listened to my classmate’s mom’s advice a few years prior I wouldn’t have been in a position to get the special education job. I always recommend asking for “Insider Tips” and networking with people in a profession you’re going after, don’t always try to do everything on your own. Luckily teaching is very flexible which has allowed me to start my own blog and marketing company in the summers!
Financial Project Manager
Bella Wanana of Bella Wanana
When I was a student, I did a lot of odd jobs such as working at a small company as a receptionist, cleaning floors in a commercial kitchen, and working as a server.
My first step into my career was that I successfully landed an internship after four grueling rounds of interview after my junior year. I have been with the same company ever since, and am currently working as a financial project manager. My experience has given me a lot of exposure to how businesses approach budgeting, and many of the methods can actually be applied to your own life to help you manage your money as well!
Sanjana Vig of youbethree.com
I’m from the midwest and currently work and live in southern California. In medicine, breaking into the California work market can be really difficult and competitive. Great weather and a chill lifestyle is a great draw! If you believe, as I do, that everything happens for a reason, then this story of how I got my job may resonate with you.
During my last year of training in NYC, I was planning a conference trip to Iceland with some friends. We were allowed one “senior” trip and that’s what we chose. However, the rules changed that last year and when they did, the only senior conference option left was one in Atlanta. Begrudgingly, I decided to just do it and give myself a nice long weekend off.
At the conference, at breakfast the first day, an older gentleman sat down next to me and we started talking. I had no idea who he was and just answered his questions as if I was talking to a friend. Finally, at the end of breakfast, I asked him where he was from and his position. He told me that he was from southern California….and that he was the chairman of the department (aka the big boss, head honcho, leader of everyone). I was rendered speechless. But I must have said something right because he gave me his email on a napkin and said, “let me know when you’re applying for jobs”.
The rest, as they say, is history.
My story is a bit unconventional, and it surprises many people, however, I think it just proves the power of networking and the importance of professionalism. You never know who you will meet or when. I had no desire to go to that conference, but the universe pushed me in that direction. Instead of sulking or complaining, I made the most of it as best as I could. Just keeping an open mind, staying positive, and taking the opportunities that come your way can open so many doors.
Robyn of A Dime Saved
I ended up at my job by accident.
After I graduated with my MBA I worked in Corporate Accounting for a short amount of time until, unfortunately, the company went under. After that came a stint in sales which I absolutely hated. I was terrible at it so I got a job at a non-profit. Unfortunately, the director had more vision than direction and that came to a quick end.
My neighbor was chatting outside and casually mentioned that she had spoken to her cousin and that he was having trouble hiring office staff. I quickly interrupted, asking if she could give him my information. He called me that night. He was looking for someone to do basic data entry and filing. I jumped at the chance. He was hesitant as I was overqualified but I told him he was getting a great deal out of it. I started working and slowly took more and more responsibility. Anytime anyone would ask if I could do something I said yes! Yes, I will run your social media account. Yes, I will do reconciliation. Yes, I will take over accounts while someone was out. Now, I am an account manager and really grateful for my position.
Careers don’t work out the way you want them to. I certainly didn’t think I would end up here. But when life gives you an opportunity you grab it. It wasn’t an ideal position but it was a position so I took it and worked myself up. Sometimes you have to do the boring work to get to the good parts.
John of Financial Freedom Countdown
I came from a third world country to the US with only $1,000 not knowing anyone; guided by an immigrant dream. It was definitely challenging to not just survive, but also thrive in one of the most expensive parts of the world. I improved my Human Capital to accumulate assets and build a net worth of $2.3M in 12 years.
I credit my early career decisions for the success in growing my income. When I took my first job in the U.S. at a consulting group based in the Northeast, it didn’t take me long to realize that many of the American born employees didn’t want to travel to middle America.
As an immigrant, I didn’t have family in the U.S. and little affinity for the Northeast. I showed my flexibility by taking the assignments in Missouri or Minnesota or other less desirable locations. Not only would I take on the role, but also I would often move to the location, which showed the client that I was invested in their success. Clients loved it and provided positive feedback to my employer which helped with annual raises and bonuses
It also set me up for a big move to Silicon Valley, where I would see a significant jump in salary. Also living in one of the hottest housing markets in the country enabled me to build substantial equity in my home which I plan to cash out refinance.
After achieving Financial Freedom at an early age, I now spend time blogging about the lessons learned, including the mistakes I have made along the way.
Marjolein of Radical FIRE
After getting my master’s degree in Finance and Control, I started to work at a financial consulting firm. Because I lived 15 minutes from the office, I freed up a lot of time to start a side hustle and make some extra money. I worked there for almost two years when I negotiated a mini-retirement and went to travel with my partner for four months.
When returning, I decided that it was time for a new job. I applied online, and two interviews later I signed the contract. My start date was April 1st, 2020. They called me the week before and told me they weren’t sure if they could still offer me the job. Because of the pandemic, they had seen a 90% revenue decline and they had stopped hiring people. Luckily, I had a key position within the company, so they decided to hire me anyway.
Currently, I’m working from home until September 1st and loving it! After reading The 4 Hour Work Week, I will definitely try to get a remote position at my next job.
As you can see, people get their jobs in all sorts of ways! Some of us are lucky and the opportunities find us, while others have to fight to get to where we are.
Everyone’s career path is going to be different. Everyone is going to face different challenges, and overcome them in different ways.
The important thing is not to give up. Embrace the obstacles. Learn from them. You will find your path.
YOUR TURN: How did you get your job? Please let a comment below and let us know what twists or turns you faced on your career path!
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