How 100+ job rejections helped this millennial land her dream remote job

How 100+ job rejections helped this millennial land her dream remote job


Rejection of any sort is always a hard pill to swallow.

It can leave you feeling hopeless, lost and confused.

The same sentiments apply to jobs.

If you are a college student reaching close to graduation and still without that “big boy” or “big girl job”, you understand this fully well. Sally had already gotten her “big girl job”.

This was her 2nd year at a prestigious advertising agency that provided her a great healthcare plan, a great salary, and awesome benefits BUT she hated her job.

According to the Medical Daily
“70% of US employees hate their jobs.”

Sally hated that she was constantly being micromanaged by multiple bosses. She was tired of not being appreciated for her work. She didn’t enjoy having minimal lunch breaks.

However,  the biggest frustration for Sally, was having limited vacation days. All she wanted was a job that provided flexibility, an opportunity to make a big impact, and the ability to travel.

Not knowing if this type of job even existed, she took the risk of making a career change.

She kept applying to hundreds of jobs for a year while persevering at the advertising agency. None of which yielded results.

Her perseverance finally reached the brim and Sally made the nerve-racking decision to quit her miserable job.

She was in a quarter life crisis.

She continued applying to multiple jobs but still kept getting rejected. At that point Sally started feeling hopeless, disappointed, lost and confused.

3 months into unemployment, Sally decided to take a different approach. An approach she wished someone had advised her on before going through that stressful process.

She finally found the perfect job that met her needs and allowed her to pursue her passion.

Here is how she did it through her unique approach.


How many jobs were you rejected from?

I applied to hundreds of jobs for 1.5 years.


In between quitting your job and getting constant rejections, how did you handle it?

I didn’t handle it well. I would get very stressed every time I had an interview. I began to worry that I didn’t have the right skill or ability to do a good job. Although I knew that it wasn’t going to be an easy task especially since I was making a career change, it was stressful having to go through the last stages of a job interview and still not get accepted. At one point, I said to myself that if I couldn’t find a job that had all the qualities I wanted, I’ll travel for a bit. I even considered moving to a place with better work-life balance. I ended up traveling to Spain.

What made you not give up? Did you do anything different?

After Spain, I started realizing that maybe I wasn’t applying for the right type of jobs. Although I love to travel and I was applying for Jobs that allowed for “traveling”, they were still same corporate jobs with little work- life balance and no flexibility. While researching for jobs, I stumbled upon this term called digital nomad – people who make a living online – I immediately realized that flexibility was a job trait, I really wanted. I wanted to be able to work online rather than be in a specific spot. I created a blog based on my two passions which are food and travel. I thought to myself that this would be a way to get a content management or social media position because that’s what blogging is essentially. My blog became my portfolio. It was what I used as a resume to find relevant remote jobs. Here is a post I wrote on finding remote jobs.


How long after you quit your job did it take for you to finally land your current position?

I worked hard on my blog for 6 months (without getting paid) and finally got a job in that area. I was able grow my numbers and social media following to an impressive enough amount that I could use to show what I was capable of.

The lady that hired me was running a startup agency in LA and I was her first employee. She took a chance on me. I don’t think that I would have been hired if I didn’t have my blog and social media channels to back me up.


What do you do now? Do you love it and why?

Now, I’m a social media and content manager for a remote agency. I manage several clients primarily in digital health. I love my job! I get to work independently with an absolutely amazing manager and research cool trends in the health and tech space. It’s definitely challenging to keep everything balanced, but I wouldn’t trade it for anything.


What are you able to do now as a remote employee that you couldn’t do in your other job?

TRAVEL! Honestly, in my old job, I was constantly fighting to use my vacation time, and now I can travel whenever I want. I used to be constantly micromanaged and struggled with really difficult clients, but now I’m fortunate to work independently with a manager who really trusts me on getting the job well done.


What are some important skills and tools one needs to work remotely?

You have to be extremely self-disciplined to be able to work remotely in any job. I think that’s really hard to do as an avid traveler. Being in communication with your boss and team members is also very important especially if the company is 100% remote. Last but not least, access to a strong Wi-Fi connection is my perpetual struggle.



What are some practical tips you can give to someone applying for remote jobs?


Having a portfolio is incredibly important. Ask yourselves these questions: What can you do differently from others?  What kind of work have you done remotely on your own without having somebody to constantly hover over you?


What advice do you have for someone doesn’t know what career path to lead?

It took me a really long time to know what I wanted to do career wise. What helped me was taking a bunch of personality tests. I know that sounds really cheesy but take all of them(There are 3- 5 major ones out there) and try to genuinely answer questions like these:

  • What kind of jobs show up based on the test?
  • What kind of skills are you best suited for ?
  • Do you work better alone or in teams?
  • Do you prefer creative or non-creative jobs?
  • Do you want corporate or non-corporate jobs?
  • What kind of salary do you want?
  • What are your deal breakers? e.g.; work-life balance, enjoyment of work, the salary, the commute, and all these little aspects.

Know that you aren’t going to come up with the perfect job but these questions help filter out what you really want in a job. For me my main desire was being able to travel. Working remotely as a social media manger allows me to live a life I enjoy.


What do you love about working remotely?

I love the freedom and flexibility it offers. I can travel wherever, whenever (as long as I have access to Wi-Fi) but I can also choose to stay put and work at home. Los Angeles has terrible traffic and I definitely don’t miss my two hour commute to the office either. Plus, it has enabled me to meet and connect with other digital nomads who are living the same lifestyle as I am. When I look back on everything I went through, I’ll say that getting rejected from those jobs helped me discover exactly what I was looking for.


About Sally

Sally is a third culture kid. She was born in Ireland, bred in California and is of Sudanese and Egyptian ethnicity. Sally has been to over 20 countries while working remotely. She is a travel blogger and social media manager. Connect with Sally on Passport and Plates, Facebook, and Instagram.


About the Author

Hello! I’m Kareemah, a content creator, and travel blogger. I love to travel to unpopular destinations, discover local gems, and meet people. Feel free to drop by a hello on my Instagram or check out my page for some tips

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