Moving from overwhelm to a great new job

Aug 15, 2018  

I recently changed jobs and I found it quite scary. Here I share some of the difficulties I encountered and the strategy I eventually followed to become unstuck, reach a decision and execute a plan.

First I’ll mention some of the problems that contributed to my indecision, but feel free to skip to the strategy part.


Is it me or the job?

Changing jobs is hard even when you know exactly what job you are trying to get and what to do in order to get it. In my case I had no idea! I knew I wanted something to change but was not sure if it was a problem due to my own internal thoughts and feelings or something actually requiring an external change. Furthermore, when thinking of getting a different job I found it hard to envision exactly what was missing, what would need to be different for me to be happier.

Over the last few years I’ve become quite aware of the fact that when there’s a pattern anywhere in life often the solution is not to run away and change the external world, but to take an honest look inside, consider how you contribute to the situation and change yourself. Some times this might mean doing the opposite of leaving, for example recommitting and finding ways to make yourself happier, getting support, meditating, making friends etc.

On the other hand if you are in a situation that’s not a good match for you there’s a limit to the amount of help positive thinking and positive attitude alone can offer. It might feel like trying to swim upstream and that it takes more effort than should be required.

Too many options

Having options is good I guess, but after a point it becomes paralysing. Because I was not clear on what exactly I wanted a new job to be like I found it hard to exclude options decisively. I get a lot of recruiter emails each week and instead of feeling happy I would feel overwhelmed. My mind has the unhelpful tendency to see both sides of a coin and reach no decision. “This job does not tick all of my boxes but it’s with a great company!”, “this job is not perfect but pays twice as much, perhaps buying a flat wouldn’t be so bad”, “this job has free food”, “this job is in haskell”. Not only does this leave me indecisive and kind of lost, but also makes it very hard to create an action plan going forward as each of these jobs uses different programming languages and stacks, and requires completely different kind of interview preparation.

Fear of failure and missing out

As someone who has done a lot of interviews that are considered hard and has a good enough CV I felt that I should be super confident about going into interviews. But that’s not how I felt.

If there was a job I really wanted I’d think I’m definitely not ready yet (fear of saying “yes” and then failing). If there was a job that I was not sure I wanted and ignored I’d fear that I might be missing out on a good opportunity and later regret it (fear of saying “no” and missing out). If there was a job that I was not sure I wanted and went through the interview process I’d worry that I’m spending my time and energy on suboptimal choices distracting me from trying to get the job I really want (fear of saying “yes” and missing out on a better job).

Needless to say being afraid of both succeeding and failing by both taking action or not taking action is a sure way to get stuck.

A strategy that worked for me

1. Reconnect with your dreams

Ok this sounds cheesy, but it is important. Some times we have dreams that seem so unrealistic and difficult to achieve that we’ve put aside and forgotten about. But as a first step it’s important to let yourself dream big and be ambitious. Even if you can’t find a job that fully matches this ideal there might be ways that some of the job options are more aligned to it than others.

Here are some questions that can help you brainstorm:

  • What kind of people in your profession do you admire?
  • How would you like to be remembered?
  • What would make you proud?
  • What kind of job would still be exciting and fulfilling in 10 years, not just after 1 month?
  • What was the best person you ever worked with and what made them so good?
  • What is your idea of a pointless job?
  • Which of your talents is the world in danger of overlooking?
  • If you were tasked with making an advert for your skills, what would you emphasise?
  • Which of your talents can you trace back to your childhood?
  • If people could learn something about you that isn’t obvious from your current job, what would it be?
  • When you look around who seems to have the most “meaningful” job?
  • What are your thoughts when you panic about the state of your career? What are some soothing ideas that can make this better in 10 years time?

What really matters in a job? Try to rank the following in order of importance. Maybe they’d all be nice but what’s the one thing that would be a deal breaker if missing?

  • twice as much money
  • prestige
  • free food and first class flights
  • opportunity for growth, build in-depth skills and knowledge
  • opportunity for more ownership or leadership
  • creativity
  • good working hours
  • impact on the world

Now look at your answers and decide what’s the most important thing in a job for you. Use this criterion to drastically cut down your choices to only those jobs that move you towards this direction.

2. Put everything in a spreadsheet

One of the problems I mentioned in the beginning was getting overwhelmed by the amount of options and by fear of failure or missing out. Using a spreadsheet is a way to make the next actions almost mechanical, taking the feelings out of the equation.

Create a spreadsheet and write every single option you have. What I usually do is insert all the jobs I’ve been mailed about in the last 1-2 months, and add any other jobs that I found myself. Feel free to reach to your network, perhaps friends in your field who went through a job change recently and add any good companies they know about.

Next, rank everything according to how much you want each job, keeping your #1 criterion in mind. You could use a scale from 1-3 or different colours to highlight jobs. Add a column for status, such as “applied”, or “need to submit coding test”.

Each time you get a new email about a job, just add it to the spreadsheet and rank it.

Example spreadsheet

3. Make forward motion

There are 2 types of actions you need to take, one is the decision-making and admin of applying to the right jobs. The other is preparing to do well at interviews. Obviously you can adjust the timelines that work for you but here’s a suggestion:

Every week: apply to the next best jobs from your spreadsheet in batches.

Every day: spend 1 pomodoro practicing for interviews, for example by writing code.

Something that helped unblock me in applying for jobs is remembering that there’s no need for 100% perfect decisions. It’s ok to take half a step forward. A first call is more like a first date, not a marriage. That said, avoid spending time on jobs that obviously don’t match your criteria.

4. Have a friend

It’s harder to do scary things alone. Some times what helps most is not technical help but a bit of support and someone who can be your accountability partner. I was lucky enough to find such a friend (hi Sandy!) and committed to sending him a daily gist with whatever code I’d written that day. That made a big difference.

I also enjoyed using Complice rooms, a virtual co-working space where people share a pomodoro timer and share what they’re working on.

Conferences and meetups where you can talk to people who are already in the kind of job you’d like to do can also be great. I am often surprised with how encouraging people are, and it’s a great way to get information about opportunites.

Bonus: it’s easier to get your dream job than other jobs

Think about it. Once you have clarified what matters most to you in step 1, you’ve come up with something that really matters to you as a person in your career going forward. The particular job just happens to be a job that aligns with your grander vision that you have for yourself. It’s a direction you would have moved towards anyway. This innate motivation can be seen through in interviews and can help succeed in the job itself.