Job Searching as a Mid-Level Software Engineer

a perspective on how to survive the dips in a broken system

Joshua Wootonn
11 min readFeb 9, 2021


Job searching is not fun. The goal of this article is to share my experience and hopefully change your perspective or help you persevere. You will find many references to my own job search throughout, but

application, interview, and offer information are in this Google sheet and resumes, cover letters, and questions I used are in this GitHub repo under 2020

I recently got a great job at Clearcover, so far it’s been a dream. How did I get here you ask? Well, that is what you are about to read. (In case you are a Clearcover employee, don’t worry, that is the only offer I didn’t include.)


I would love to include details on how I got to my job search, but alas, non-disparagement agreements are a thing. Instead, I’ll tell you a story.

I graduated from the college of early childhood amusement in May of 2019. Despite my best efforts, I could only land a job at a zoo close to home. While it was nothing like the zoos you might find in LA or NY, my stay turned out to be a huge blessing because it kept me here in Iowa long enough to get to know my future wife.

At the zoo, I met many different animals. I learned a lot from these friends and hope to tell you more about them in the future, but for now, let’s start with the Badger. The Badger was a bard. He talked in stories about his Russian heritage but in a way that made you learn about the present. He took action and ownership of the zoo, which meant many of his Mondays were spent entertaining children and many of his late nights spent fixing the toilets. He just wanted to see the zoo flourish. There were many problems, however, and despite his and many others’ great efforts, the conditions of the zoo weren’t changing anytime soon. He was quite vocal about his dissatisfaction and because of this, the zookeepers saw him as a threat. By July 2020 he received a Performance Improvement Plan, a means for the zookeepers to make him leave. Soon after he let the zookeepers know he would be switching zoos in two weeks, but due to some banter in Bills’ slack clone, he was kicked out of the zoo prematurely.

The whole ordeal was enraging. I tried to stand up for the Badger and talked to the zookeepers about the lack of respect they had shown my good friend. They had lots of excuses. “His words were not constructive or nice enough.” But ultimately a lot of problems had persisted for the years he had spent there; his banter was well deserved.

A wise, gentle, yet stubborn friend joined the Zoo in 2020 — the Elephant was his name. This article and much of what I have learned in the past few years are a result of his mentorship. In a conversation one day, the Elephant mentioned a book called Linchpin. I don’t remember how he described it, but it struck a nerve with me. Linchpin describes the traditional manager/employee dynamic that capitalism brings, it then points out many of its flaws and urges its reader to make their own map to get the changes they want.* For a long time, I had lived the life of a good employee following the “best” path. Linchpin showed me that I was not following the “best” path, but really the safest one. The one that would get me job-security and not the adventure I want out of life. After reading it, I felt empowered to leave that zoo and the security it had brought me.

*Note: that summary is a grotesque simplification. Read the book yourself!*

The Search Begins (July and August)

Part of making my own path was altering my job search. In the past, I had shotgunned resumes with low-effort cover letters, and according to the Elephant, these had to be a thing of the past. I created a newer resume and tailored my cover letters to where I was applying. This process routinely took 1–3 hours per company.

Strategy Version 1

Mantl(href, questions, details) was the first company I applied to. It embodies many of the things I wanted and I wasn’t expecting a response let alone multiple interviews. Unfortunately, it fell through, but I was convinced that my personalized cover letters were working. This fluke cost me big time because, in retrospect, I realized personal cover letters were a dead end. It took 42 other applications and over 158 hours of job searching for me to realize this.

Summary of July and August

LinkedIn recruiters (September)

By September I was still lacking any real traction. In my desperation, I started responding to recruiters on LinkedIn. I was exhausted from working full-time, working on a consulting project, and looking for jobs.

**Hot Take Alert**

Using a recruiter is low effort job hunting. Often good things in life come from great effort.

I discovered by talking to thirty-one recruiters that most of them were just headhunting for buzz words. If all you are is a human cache of documentation and don’t mind being a cog in a wheel, this method might be helpful. But for someone seeking to show their expertise, using a recruiter doesn’t provide any means of differentiation. There is a lot more to say on this subject, but I’ll leave that for a later time. There was one recruiter out there (Logan!!!) who cared a lot. This kind of relationship was rare. Beware the recruiter.

Ultimately I got two offers from recruiters at, questions, details) and UFG(href, questions, details). Picking between the job offers was incredibly difficult for me.

In my mind, UFG was a slow-moving machine in a boring domain with great people and benefits to prove the company cared, while Seamless was a popping startup with some hip people, a faster-moving environment, and an unhealthy culture around work expectations.

Monday night: I got an offer from UFG

Wednesday night: I received an offer from Seamless. It came much later than I was expecting so I was nervous and I felt led on. In frustration with how long I had waited and how short the PTO was, I verbally accepted UFG’s offer that night.

Thursday morning: I woke up knowing I couldn’t go to UFG.

Yes, Seamless had pissed me off with a lower offer, but my top priority was the ability to learn and grow. Seamless better aligned with that priority. This was a hard decision because the Seamless recruiter had mentioned needing to work overtime and had wanted to clarify I was committed to getting the job done no matter the cost. In my mind, this was a given, but the fact that they were so insistent made me uncomfortable. I convinced myself that it was the right thing to do.

“You’re married and you need to provide while my wife is in school … Jobs are just temporary, it won’t be forever.”

I reasoned with myself. I tried to remain enthusiastic, but the week before my onboarding started any negotiation I proposed was rejected. After getting some advice on Blind and confronting them about a potentially predatory clause in their equipment agreement, I came to a realization: I had 12k in the bank to keep searching for a company that actually cared.

It seemed like everyone was telling me to take the job except for the Elephant. This is so corny, but the Elephant believed in me and he told me to hold out for a job that was worth it. So I canceled my onboarding and rescinded my acceptance. Relief washed over me. It felt like I was flipping over a new leaf and betting on myself for the first time. And despite what my amygdala(or monkey brain) was saying, I was free to do so. That was wild.

Summary of September

Starting Again (October)

I learned some big things in October.

1 After reading Tribes, I realized that I had lived in a bubble. I really only knew developers from the local zoo I had been a part of. Despite the opportunity of the internet, I had lacked the courage to put myself out there and build online relationships with other developers. Referrals are the easiest way to get a job, and I didn’t have any.

2 After reading the Dip, I weighed the pain of an extended, risky search with the joy of a fulfilling and challenging job. The dip is the difficult part between starting something new and finishing something worth doing. It felt like a dream to imagine myself working for any of the companies I was applying to. The Dip played a big role in seeing this tough season as just that, a season I had to push through.

3 I defined what I thought was a“cool” job and what I thought was a “sucky” job, and I applied accordingly.

These realizations were followed by a wave of self-doubt and exhaustion later in the month. Not only was I in the dip of my job search but I was also in the dip of a consulting project. So I got on my knees and crawled back to UFG. I wanted to maintain my dignity but the recruiter for the job required me to beg. I was at my wit’s end, so I did.


Thankfully they rejected me. I was once again sooo relieved. I plunged into thoughts of “just give up” but quickly trekked up and out of the dip, spurred on by my newfound perspective to get to the results I wanted.

Summary of October

Letting go of what once worked (November)

When you have been doing something for a while, it is very difficult to remain unattached. I was attached to my cover letter style by now. In a conversation with the Elephant, I was called out on something I already knew deep down inside: I hadn’t switched strategies since the beginning.

Why are we so averse to change? I think this is a common pattern I see in people; they find one thing that works and they double down on it for far too long. I had put the time into these custom cover letters and by now I was really comfortable with what I was doing. I had a process and I had clever phrases to present myself differently to companies of differing genres.

In the second wind of energy that followed UFG’s understandable rejection, I made a new cover letter template with the help of my wife. By this time I had also gotten my resume reviewed by someone on Rooftop Slushie and by the Elephant. I started November with a burst of energy and a new approach. Praise the Lord for his timing on that and the change in my heart to adjust my strategy — it would turn out that I would finally land a job with the first company I sent my new cover letter to.

Strategy Version 2

With this new cover letter, my interview rate went up. I still struggled to convert interviews to job offers, and thus I entered into another dip, getting rejected by Bright Cellars(href, questions, details), Collage(href, questions, details), Formidable Labs(href, questions, details), and others.

In the midst of this dip and later in the month, I realized I needed to press pause on the job search. I had stopped working out and become dependant on my wife for getting the chores done. In the midst of it, I had shifted much of my agony onto her. We fought a lot about it, which caused me to realize that companies are looking for people, not drones and my search had turned me into a drone. So I pivoted, deciding to stop applying for new jobs and only complete my remaining interviews. The rest of my time was focused on finishing my consulting project.

Summary of November

Things falling into place (December)

On the first of December, I followed up with Clearcover after a technical I had completed two weeks prior. Assuming the worst, given the slow response, I was surprised they were moving things forward. I was still burnt out in early December, but I put a smile on my face for interviews and tried to hide the turmoil I was in. I was also continuing the process with some other leads at Articulate(href, questions, details), Dropbox(href, questions, details), and John Deere(href, questions). My mental was really fogged so I remember thinking:

if I don’t get a job at Clearcover, I am done for.

After getting through two interviews with an HR rep and my future Manager, I got a call from my internal recruiter. He had warned me that we would be talking money, and I had prepared myself ahead of time with a range I was happy with and a bluff number that was higher than I was expecting.

Note: if you are going into negotiations without a plan you are doing it wrong. This article was super helpful in getting context for how to think about negotiation

I tried to not reveal a number first, but after the recruiter’s persistence, I gave in on the third ask and revealed my bluff.

A week went by.

Turns out the recruiter had some family emergencies, and another recruiter reached out to me after a painstakingly long week. I remember standing in my living room with my wife, both of us anxiously holding our breath as the phone rang. I was fully expecting a rejection and trying to prepare my heart for it. The recruiter was apologetic to start, which made me think “they were moving forward with other candidates.” Turned out, he felt bad for how my application had fallen through the cracks. He then verbally offered me a job at my bluffed price! I remember almost falling back into the door, weak in my knees, exhausted and electric at the same time.

Summary of December

Clearcover is a dream job. I am so grateful to be working here. The people have been soo kind and the work has been challenging but also enjoyable.

I got a job at Clearcover not because of my strength or my might. But because God opened a door for me. Praise the Lord this season is closed!

Huge thanks to 🐘 Aleksey Gurtovoy, the Elephant. He chatted with me late on Friday nights, he gave me a lot of clarity in the midst of my mayhem, and he believed in me to get me to the next level!

Lastly, I want to thank my wife. She was a huge rock in my life, pointing me back to Christ, talking me down when I was overwhelmed, doing well over her share of the relationship for a good while there to just keep us afloat. I love you.

This article is just the beginning of what I have written on job searching. You can find out more on the topic on my portfolio.