Ask HN: I'm rebooting my life, and could really use your advice.

19 points by throwaway202 ↗ HN
I'm rebooting my entire life.

I'm moving to a new city (Philadelphia), I'm getting married in six months, and I have over $100,000 in personal debt ($70k credit card, $30k IOU to my co-founder) resulting from the failure of my previous business.

My focus is on being a reliable provider for my soon-to-be family.

As such, my immediate goal is to get a corporate job, but I need some advice:

Question 1: How do I find somebody to help me write my resume? I want to find somebody who can understand the cross-functional role I played as a founder/COO and help me express that experience and my skills effectively in a resume.

Question 2: Once I'm happy with my LinkedIn and my resume, how do I go about finding a good recruiter and/or appropriate jobs in a town where I have thin personal and professional networks?

I'd really appreciate any guidance at all. I'm hoping to start the job hunt in earnest in early January.

26 comments

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I think you're going about it backwards. Let me get this straight: You're moving to a new city without a job and getting married in 6 months with 100k in debt? Yikes. You're resume and LinkedIn can wait (or be done on the side at night). Start networking NOW! Job 1 is getting a job. Best way to get a job is to be introduced. Talk/email/call/bang on the doors of everyone in Philly.

Good luck with the reboot.

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).

Why are you moving to Philly to begin with? Is your wife's family from there? Why are you moving to a city with no contacts and no job offer?
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.

"Possibly relevant professional events" are the 5-10% of what you need to do. Most of those events are just drinking and schmoozing with little benefit and even less follow-up.

Have you identified potential places of employment? Have you posted on relevant local boards? Have you called up/met with any recruiting centres that focus on Philly? Have you contacted the HR departments of companies that may fit? Have you spoken with the Philly board of trade/commerce? And stretching out, how about the local chapters of the Knights of Columbus/Shriners/other social groups? How about your university/college alumni? Facebook? Have you extended your possible career choices to include teaching at a community college (I know one guy who did that)? Have you checked with the city and what jobs they have (municipal governments are all hiring IT guys these days)?

There are lots of ways to find a job. Sitting in front of your computer, browsing Monster/Craigslist/etc. is not the best way. The holidays definitely put a crimp on opportunities available right now so you should, IMO, be taking the initiative to introduce yourself to those who may have openings in the next couple of months. First the introduction, then the reintroduction after the holidays. That shows drive, determination, and desire.

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.

That's a tough one. Persistence and lucky timing could help if you can't get a direct and personal introduction. Till you get the introduction it will all be about persistence.
I'm not sure you can reboot your life with $100k debt though...
Network first. Start with your network locally and ask if they have contacts in Philly. Join some meetups in Philly.

You write your own resume. Don't spend more money doing that. You know yourself best. Then get your friend to review.

Don't expect to get the perfect job right away. Get any job and start paying down your debt! Once you're settled and your network is more established, you can look for other opportunities.
From a young developers perspective Philly was fun. Lots of events, low living costs for a decent city and tons of web work. I was able to easily freelance with few contacts.

A previous co-worker on the other hand (usually working in the very top of a company) found Philly to be difficult as he had too much experience in high positions and expected to find it again and again with a cushy salary too boot. Its been over a year and I still think he is out of work.

Pharma while soul crushing will get you the fast cash you need, is abundant and should be easy enough to get into.

You should write an ebook on how to find a fiance and move to a new city while being unemployed and having $100K in debt. This would be more interesting than any of the advice you're going to get about how to find a tech job in Philly. Maybe you could sell enough of them to pay off your credit card. I'm only being about 10% tongue-in-cheek. I'd buy it...
With $100k of debt, I'd consider a marriage a "luxury" that could wait.
Why? You don't need a lot of money to have a unique and meaningful wedding.
I'll take a stab at this. First, a few assumptions:

1. You have no children 2. You are currently single 3. You are technically savvy 4. You are healthy, probably relatively young (20's) and able to work.

If those assumptions are all accurate, then I offer this: Hit the power button and reboot again.

Marriage, as someone else said, can wait. Finances cause a lot of marital problems. This, of course, is optional. Get married if you want. But I think it would be better to do so with a clean slate. Your first years of marriage should be joyful and full of intimacy. It's hard to do so when you're financially strapped. It's just an extra source of stress you don't really need.

Since you currently don't have other baggage (kids, wife, mortgage, presumably pets) -- how about another stab at doing a self-employment thing? Do some consulting work to get some cash flow and build work on a business you might enjoy. Once the wife and kids and house and dog and cat and picket fence come along, that's going to be a real bitch of a thing to do without significant cash reserves. I know, because I've got first hand experience and have limited myself and my options as a result of my choices.

A lot of people fail at their first (and subsequent) business attempts. Surely you've read this all before. Wouldn't it suck to quit right before you got it right?

But, forget all that crap! Right? I get it. You want a little stability. Good! But, will you be happy? Will your corporate job fulfill your passionate needs? Will that steady paycheck make you happy? Perhaps. If so, do it!

How about getting that corporate job and seeing if you like it? Before marriage! Hey, if this person loves you, they'll wait. No rush my friend, right? Or am I wrong? If I'm wrong, then maybe you better think twice.

Now, you got your corporate job, you aren't married, you have no kids or house or pets and picket fence --> you have options! Selfish options at that. Step out and get back to your thing.

Oh hell, I probably said too much. Good luck and smart choices to you. And...my sympathies for the debt - but don't let it destroy your spirit. Life is a roller coaster - the nice upside will pay you visits in your future and you'll look back at this as a great education.

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.

It's tough but if you made 100k consulting could you either a) do it again or b) tell (charge) others how to do 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.

That's a great story and a good strategy, which you pulled off admirably. Reading that, I don't think you should pull a 180 once you get to Philly.

I hear what you're saying about your distaste for the 'lone wolf coder' role but you can use your skills and experience to hit the ground running instead of hunting for jobs until you catch one. The networking advice is all well and good but it doesn't pay the bills and it's not a quick fix. You network so that you can call on your contacts in times like this, starting now just delays the payoff and poisons your interactions with dread that you have to hit them up with your plea sooner or later - or worse, right off the bat. Networking is about building a rolodex, give and take, but mostly building relationships. If you need something right away it ruins the premise and people can smell it.

My advice is this: Philly must have coworking space. That will solve your 3 problems. You can be with people. You can help them, and receive help. You can advise, consult, contribute. Make money, join the community and networking will be a part of your life. You can hunt for a job for a few hours a day, but help people and they will help you. You'll become a part of your new home, and your new life. You may even like coding again.

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.
Thanks, I'm in a somewhat similar boat (I'm motivated by working with passionate people) but I need to pay off debt accumulated from mistakes over the last year. Your method will be worth a try.
Me being blunt.

Find someone to help you write your resume? Why can't you do this yourself? You are just offloading responsibility. It takes a day to do and is fairly easy.

Find a good recruiter? Cannot you just start applying for jobs now? Why do you need a recruiter? They can be helpful but as you need a job as soon as possible you shouldn't limit yourself here.

Finally, starting the job hunt in early January is procrastinating. Get up and start applying now. There is a pre-Christmas lull in many offices that make it a good time to hire.

Good luck with your job search.

(comment deleted)
To answer your questions:

- I wrote a resume. That said, I believe that somebody who deals in resumes all day, every day will have useful guidance in how to convey my skills and experience in resume form.

- My experience is that many of the better jobs aren't listed in the typical spots. As such, a good recruiter can help me cast my net more effectively.

- I'm pushing the search until January because I have out-of-town obligations on 10 of the 12 remaining business days this year. If somebody is interested in me, I want to be available for the interviews.

Sounds like you've thought this through. Congrats to your fiancee for landing a great gig. You are a true partner for making this move.

Since no one else has said it, find out which alums from your university are in Philly and set up informational interviews with ones in fields/jobs you find interesting. Everyone loves to talk about what they do/how they got to where they are. Key: follow up with a hand-written thank-you note. This is far more memorable than an email! (and do this for everyone who takes time to talk to you)

I would also set up an informational interview with these Philly folks to get a better idea of the local scene: http://www.dreamitventures.com/ I totally get that you want a job-job, but they will "get" your background and may even put you in touch with one of their companies and/or introduce you to others in the Philly tech community.

I'd also check out http://asktheheadhunter.com/ for advice on how to treat your job search the way a recruiter operates in matching companies and talent (essentially, you research the heck out of a place where you'd want to work and then show them how they need you). The "Ask the Headhunter" book is a bit repetitive but may be worth picking up as well.

Best of luck! And don't be too hard on yourself. The process will most likely have its setbacks.

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.