Career Crossroads and Deciding What is Next

I have had a pretty good career so far, gone from college to running my own technology company for 10-years, selling it and taking on some interesting software development and lead roles for a few companies and fast-forwarding to now where I am an independent software developer.  

My current large client project is coming to an end as the project is losing funding.  I have some smaller projects I work on but I have had a single project for the pas couple years which paid the bills and afforded me to take on smaller stuff I enjoy.

What I have done

I do have a diverse and solid technology background:

• Windows Forms Development with C#
• ASP.NET Development with C#
• Ruby on Rails Development
• Software Architecture and Design
• Project Management

I have acted as a software architect on many projects as well as the project manager on others managing completely new development.  Running a company also provides this type of experience as well.

In the past couple years I have gotten more involved in writing, mostly technical, for this blog and for InfoQ as well as a book on IronRuby.  I enjoy the writing a lot more than I thought I would and want to keep it up.  The downside, it does not pay as well as coding or at least I haven’t found a way to make a living with it just yet.

I don’t really maintain a resume any longer, the post by Rob Walling on the subject rang true to me.  I don’t think it’s necessary as I never plan to go work for a mainstream company who requires one.

What I want to do

So with my biggest client going away I need to make some decisions.   I need to decide what is best for me to do next.  I don’t have any answers, just some pondering to help my thoughts a bit clearer to myself and maybe to help someone else faced with a similar decision.

Some of my options are obvious, some maybe not:

• Get a new big client to write code for and stop thinking about it – this is probably the easiest option I have as writing code by the hour for a single company is not that hard to find.  The drawback is that I am little more than just an employee with no benefits.  The plus side of things, the pay is usually really good.
• Get a bunch of small clients to write code for – this option is a bit tougher to land a bunch of smaller clients an be able to juggle all of the demands of the work.  These types of clients usually pay by the projects and from experience, are feast or famine.    The upside, you are really your own boss and have more control of the work you want to do.
• Stop contracting all together and create the software product company I have always wanted – this is very attractive but very risky.  I am full of ideas but ideas are cheap and it really comes down to the execution.  The cost in time up front and the amount of time it may take to make a living could be very long.
• Get hired by a large company to help get a  product off the ground, evangelize and manage – I have thought working for a company like Microsoft would be a great experience.  I have seen folks like Scott Hanselman, Rob Conery and Phil Haack move from smaller companies to Microsoft and appear to be having a great time doing it.  I would think being involved in ASP.NET MVC or IronRuby would be a really cool way to spend the day.
• Get hired by a small company to have a bigger impact to get a something cool going – I have done this already and it is very rewarding but has drawbacks.  The pay is usually not as good and the funds to do a project are less, which is understandable.  I think this is less appealing but getting in the ground level of a company like HashRocket or Engine Yard would be a great time.  It would be good to have some equity, which really makes the challenge that much more rewarding.

Some things important to me when thinking ahead:

• No commute – probably number one.  I hate driving and facing the crowds of cars and trucks in any of the cities I could possibly commute to (Hartford, Providence or Boston).  The high price of gas, the great home office I have and the time wasted in traffic make commuting a huge downside for me.  I don’t mind traveling from time-to-time.
• Quality of Work – I won’t be writing the next claims system for Travelers, I just as soon poke my eyes out.  I think the less-enterprisey the work the better.  I see a lot of really cool stuff going on in the Ruby community and I am sure there are plenty of those kinds of projects in many places.  I really want to be involved in something that can make a difference.
• Flexible Hours – it would be nice for a change to work when inspired.  Yeah, this sounds artsy, maybe it is.  I think writing code at 2:00am because I want to versus at 9:00am because I have to would be a plus.
• Attending Conferences – there is something to be said for the conference crowd and the relationships created during these events.  I want to attend more, meet people and maybe even speak at some point.

I am too old and have too much experience to be starting at the ground-floor of a company, so this will never be an option. 

So, what to do?

I this point I don’t know what will be next.  My large client contract ends around the middle-to-late July.  I am attending RubyFringe the third week of July and plan to take vacation time with the family the first two or three weeks of August, haven’t really decided yet.

I am looking my readers thoughts on this as well, I am sure you have a lot of experience with this.  If you want to pass along something either leave a comment here or send an email to rbazinet AT gmail dot com.

If anyone has an interesting project they would like to pass along, please do that as well.  I am open to hear about possible partnerships or just about anything.  The good thing is I am not desperate for work and see this as an opportunity to step back and take on something important, something that will have an impact on the world.  Suggestions welcome.