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!