So you decided to take the plunge. Now what?

Christian Pearce
pearcec
Published in
7 min readMar 28, 2021

Transitioning from one company to another is stressful, takes a lot of work and calls for careful planning. In my last article, I discussed my personal experience with the decision to leave my last job. In this article I discuss the “now what” part of leaving your job.

Christian jumping off a cliff in Costa Rica

The obvious next step is finding a new job. Take some time with this step. Finding a job is an investment in your future. Consider this, you spend about ⅓ of your daily time working for a company. The amount of time you take in finding the best company for you will pay in dividends. If you put in the effort to get a good match, it will lead to better career development, life satisfaction, and reduce the likelihood you will want to leave in a couple years. Simply put, apply as much effort in looking for a new job as you would planning for a vacation, buying a car, or looking for a house.

I realize the idea of picking a company is a luxury for some. There are always extenuating circumstances in your field or life that will cause you to take a job with a company that may not be ideal which is okay. Make the best of it, and try again at a future date.

Knowing why you are leaving a company is an excellent roadmap to finding a new company. What have you learned from your past experience worth examining? For example, what about your current employer do you like or dislike. Take into consideration the size of the company, and the industry. Does the company make products or sell services? Who runs the company? What type of culture does it have? What are your job duties? What type of company might make better use of the skills you have recently developed? Explore the characteristics of the company. Do you have strong opinions about them which might shape the search?

Similar to my discussion in my article “Who are you? Have a vision” in which I discuss having a vision for yourself, you can have a vision for your next company. While working for Hershey I started to make notes about what I might want in my next company. When I finally decided to leave I had a list of what I was looking for:

  • A company where I could develop code in go or rust
  • A place that engages freely in open source software
  • An engineering led company
  • A strong remote first work culture
  • A DevOps test driven development workflow
  • A product targeting software engineers (ie a platform/SaaS) or physical fitness
  • A place where I solve problems by writing code

Although not quite a vision statement, this type of list helps guide you with your decision making. It also works as a set of questions you can use during the part of the interview when they ask, “Do you have any questions for us?” Asking these kinds of questions are a good signal to a future employer you are giving careful consideration before you join another company.

Over the course of a long career it is common for roles in a field to change and grow. It is common for you to change and grow. I started out as a developer and moved into systems administration. Now I am an SRE. With each move, there is an opportunity for you to switch roles as you discover more about yourself.

When looking for a job I applied the funnel theory, best expressed by Jack Conte. Essentially, you need to talk to a lot of people, and fill out a lot of applications to get some callbacks, to get a few interviews, to get a couple of offers.

Start a spreadsheet, tracking who you’ve talked to or where you’ve applied. For context I contacted or filled out a total of 19 people or applications. I considered about 20 more places before I finally accepted my offer with Stack Overflow.

There are a lot of dos and don’ts with interviewing, and resume writing which are covered ad nauseum; moreover, the rules seem to change every 3–5 years. Nevertheless, there are a few timeless key points I follow:

  • NEVER lie about your experience on a resume. I feel like this goes without saying, but I read so much about it happening I think it needs to be covered. Lying makes you a fraud. It will catch up with you.
  • DO write a very thoughtful and job specific cover letter. This is your one chance to highlight why you are a fit for the job. Each cover letter doesn’t need to be written from scratch, but take the time to highlight a specific project or skill set that matches the job description.
  • DO tailor your resume for the job you are applying for. Similar to your cover letter, there might be key highlights in your career that are better fit for one job over another.
  • DO include specific numbers on your resume. This helps a future employer understand the scale of your experience.
  • Be YOURSELF when interviewing. If you put on a persona of someone different during the interview you will always end up second guessing yourself (more than normal) about who you are and how you fit into the company. When you do get an offer, you know they want the REAL you.

Based on my personal experience it is extremely difficult to get multiple job offers at the same time, unless you are fresh out of school, working with a job placement program. Companies move slow, and will not match your timeline. As a result you need to take each offer as they come and consider them in the moment.

When reviewing an offer, FOMO is going to creep in. Is there a better job offer out there? Could be. However, if this offer meets the vision of the company you want to work for, does it matter? Is the offer good? Do you have a good feeling about it? I recommend against holding out for a better offer if you have a good offer in hand.

The way you leave a company is going to vary based on how you feel about the company, your manager and the people you work with. Hopefully, you are leaving on good terms, but even if you aren’t, it is still not worth burning a bridge. You never know where you will find yourself in life, or how you will change. Here is a list of things to consider when leaving:

  • Give two weeks: Once you have a signed offer, tell your manager immediately. It is courtesy to give two weeks notice. If they want more time, ask them what they want you to accomplish. There is no reason to say no if it is a reasonable request, and your future employer is comfortable with the adjusted timeline. There is no obligation for staying beyond two weeks.

Leaving in the middle of a project is considered poor form. Possibly, if a company is treating you badly, turnover in the middle of a project is a signal they need to do better. Often projects feel like they are never done. It is acceptable to leave after two weeks, or wait for a major milestone to be completed so you can leave the people in a good position. But don’t feel obligated to help over and above.

  • Leave the counter offer on the table: If you are given a counter offer, I would pass. Getting an offer from another company signals to your current employer a couple things, one you don’t want to work there which means they expect you to leave at some point. So if you do accept a counter offer, they will always think twice about growing your career with them. It also signals you lack conviction and are swayed by money. Nothing about the remaining circumstances with the company will change or have a lasting effect.
  • Make connections: Make lasting connections with people, by giving a thoughtful goodbye. This is a really excellent time to write recommendations for people on LinkedIn, especially for people just starting out. Back to the funnel theory, if you are hoping to receive a recommendation it is going to take you writing a lot to receive a few. I wrote twelve when I left and received two.
  • Give yourself time: If possible give yourself a few days to a week to decompress and center yourself before starting with your new company.

My last bullet point is key to a good transition. Take time to reflect on who you were and who you want to be. Work on that vision for yourself. What bias and bad habits do you want to change about yourself? Here is an example list of bad habits worth changing:

  • Stop being arrogant, prideful, a gossip, a complainer, or defensive.
  • Stop scapegoating, and talking behind people’s backs.
  • Stop arguing with people.
  • Stop trying to have everything go your way.

What good habits do you want to develop? Here is an example list:

  • Learn to understand your biases.
  • Learn to have strong ideas, but hold onto them loosely.
  • Help others when they ask even if you are not required.
  • Accept ambiguity and learn to work through it.

When you do start that new job, there will be a honeymoon period. Enjoy it as long as possible. Write down your thoughts and feelings for later. Eventually the new job will be your job, and you will experience hardships and disappointments. Refer back to the vision you had for the company you were searching for, and how it made you feel when you started. No company can live up to your expectations completely, learn to accept it. After the years roll on, reread my “So you are thinking about jumping ship. Why leave?” article if you are feeling the urge to leave.

When you do get hired, remember they picked you. You belong. Do things. Be awesome.

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