throwaway202

Thanks for suggesting coworking space. If I decide to burn off the rest of my debt via freelancing, that'll give me at least a shot of sanity.

Awesome ideas. I've had coffee with people who were far more successful than me many times in an effort to understand how they did it. It hadn't occurred to me to do the same in this situation.

I just added a todo to my calendar to contact DreamIt as soon as I'm in Philadelphia full-time, because that is absolutely brilliant. I might be able to go "corporate" by working for a portfolio company, or perhaps somebody in their network would clearly understand what I bring to the table.

And frankly, even if none of that works, once my debt is cleared my wife wants to found a startup so it'd be great to have a better handle on what DreamIt is doing.

I know this isn't a memorable hand-written note, but I can't tell you how appreciative I am for the advice and ideas. I truly appreciate it.

Here's how I did it, for free:

I spent the first month putting together a 'web dev' resume. This took a month because most of my experience was non-public, involved large teams, and/or NDAd. As such, I supplemented my resume by writing a few applications that while not overly complex, were clear demonstrations that I can do more than a basic CRUD app. (After all, I've got more than a decade of dev experience, it'd be weird if I couldn't do that.)

I further emphasized that competence by opening a github account, submitting a few minor patches to other projects, and open-sourcing one full application of my own.

Once I finished that, I started scouring everything I could find for jobs and contracts where I might be a good fit, and I applied to approximately two per day. I started with a 'take anything, as long as it's short' approach, and got pickier over time about what I'd do, and the rates I wanted.

After about two months, I wound up working with a client who was incredibly impressed with me, and wound up buying about 50% of my capacity for $100/hr on an ongoing basis. Most weeks I wound up working 20 hours for him, and the rest of my time was spent trying to land small-ish higher-pay contracts, or working on those higher pay contracts.

Altogether, I grossed about $160,000 in a year with almost none of that coming in during the first two months. The vast majority of that cash was used to pay off corporate debt that was personally guaranteed.

The only reason I don't want to repeat this is because while it would help clear the debt, it left me deeply unhappy. I don't enjoy coding anymore, and I don't enjoy working alone.

A few reactions to this:

- No kids, engaged, I have strong technical skills (10+ years of dev and ops experience, lots of IT project management experience), I'm healthy, in my 30s, and I am ready, willing and able to work.

- Marriage rescheduling isn't on the table. The wedding was supposed to happen last year but got nixed because my business had just entered free-fall and I was a ball of stress. Now the situation is crappy, but well-defined, so I no longer panic about finances. She would wait again if I wanted, but that's not what I want, either.

- I did quite a bit of consulting in the past year, as we were winding down the company. The positive side was that the pay was fairly good and it helped scrub a lot of debt (there was a point where I was down close to $200k.) The minus side was that I felt stressed by having what was more of a collection of part-time jobs than a business or a career. This downside is amplified by the fact that I stopped enjoying dev work, hate doing outside sales, and I legitimately miss having to go to an office each day.

- Right now, a steady paycheck is exactly what I crave. I have a roadmap laid out that includes both a corporate and an entrepreneurial fork, but both start with me working in the PMO or IT PMO of a relatively large corporation for the next four years, then move to Singapore and attend INSEAD.

- Thank you for your post. I'm extremely grateful for everyone who took the time out to offer their thoughts.

- The debt really isn't that bad. I paid $100,000 for a transformative experience. If you gave me a time machine I'd do it again.

Thank you so much for an incredibly helpful post. I've done about half of what you suggested, which means that half of it is new to me.

One follow-up question for you: Do you have any advice on how to contact the HR department of a candidate employer and have a conversation that's deeper than 'yes, I will send a cover letter and cv'?

Thank you again for taking the time to list some specific ideas that I hadn't considered.

My wife-to-be got a great opportunity and she wants to pursue it.

My assumption is that I bring enough value to the table that I'll get a job as soon as I figure out how to frame my experience in a helpful manner and meet more people.

Not to be daft, but what all would you do to 'start networking now'?

I've added a few possibly relevant professional events to my calendar, and I'm trying to get to know my neighbors but it doesn't feel like nearly enough and I've had trouble finding more (particularly with the holidays, which seem to have killed a lot of the late december events).