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by someday_somehow 2055 days ago
Thank you so much for posting this! I found many things in your story that are similar to my experience and it gives me hope.

I have a few questions I hope you don't mind answering as I'm trying to change careers to work full-time on public cloud for a technology driven company.

A little backstory (feel free to skip):

I began my career working in a company that did structured cabling, PBX systems and rack and stacking data centers. I was rapidly taking on more responsibilities and was managing a team of 40 people within 2 years.

Things were steady but I felt like I was missing out on all the incredible things that were happening in tech (I spend a lot of time on HN). After discovering AWS I was blown away by the possibilities and decided Linux and cloud were what I wanted to focus on as a professional.

I resigned to start my own consultancy and got the pro level AWS SA certification (with mostly self practice and no real-world production experience) and approached many businesses to sell services as an 'AWS certified' consultant. I got a few small wins but the sales cycle was longer than I expected and many potential clients would engage in long technical discussions but then cancel once they saw the TCO calculations.

The unstable cash-flow made things like paying rent on time very stressful so after two years I got a job at a small consultancy that provides mostly on-prem IT infrastructure services. I've learned quite a lot over the past two years and realized there were many holes in my knowledge. Yet, most of the clients' work was still on premise and now because of the pandemic many of them put their projects on hold or outright canceled them to cut costs. I've been furloughed without any income and right now I'm trying to survive by installing internet in homes and taking support calls while looking for a new job.

Many of the cloud related jobs - either solution architecture or Devops, require experience working in an agile software development environment, which is something I don't have and I have a major case of imposter syndrome because of this.

Now for the questions:

1) Is it possible to learn enough about agile practices and development to be productive without real-world production experience?

2) When you were looking for a 'real job' after running your own IT business, did you face any objections during the recruitment process on why you were looking for a job despite running your own business?

3) I was thinking of applying for 'cloud support engineer' type of roles because I really want to work in this field, but would that be a negative signal to recruiters because I'm an experienced (albeit in other areas) candidate?

After all these years I started to question if it was possible to go from rack and stacking to cloud but since you've explained it in such detail I see a path now. Thanks!

1 comments

1) The answer to this lies in the question. Agile is a practice and it'll take some to get up to speed. One path I took was taking jobs in tech support, answering phones calls, and finding opportunities to engage with the product teams. You can start by giving feedback on the top issues you're seeing and breaking down ways the product can improve to reduce related support calls. And Boom, you are now apart of the Agile process, providing a feedback loop that helps development teams incrementally improve the product. You also help reduce support cost; don't worry, if you automate yourself out of a job, there will be a better one waiting for you.

That's how you open doors for yourself. Many great Q/A and operations engineers started in tech support where they honed their troubleshooting skills.

2) Yes, I use to get those questions. My answer was, "I'm starting a family, and I'm looking for something a bit more stable, and bigger challenges than the ones I was getting on my own".

It's all about being able to demonstrate your skills. Some times it's whiteboard coding exercises or logging into a live system and "making it work". My IT certifications helped me earlier in my career and now things like GitHub and blog posts are a great way to showcase your skills.

3) Remember, you can always tailor your resume for the job you want. If you want to avoid looking over qualified, then re-frame your experience to align with the job requirements. Instead of "I ran a business doing X,Y,Z", you can re-frame it, "As a _ I did X,Y,Z".

During the interview you can show off your full skill set by giving deep answers demonstrating your understanding of the big picture and how to make a business impact.

If you ever want to discus this stuff further, shoot me a DM on Twitter, I've been where you are, and I know what's possible.