The pleasure of being a lone wolf

The WordPress consulting world has, of late, been all about consolidation and upsizing. Firms get larger by hiring independents and acquiring smaller businesses. Every week I read countless tweets and blog posts about the joys of working for a larger team: the camaraderie, the efficiencies of scale, the pleasure of getting a regular paycheck. And as a longtime solo freelancer, I’m very sensitive to the shortcomings of being a lone wolf.

At the same time, I try not to forget the beauty of going it alone. First and foremost is the flexibility. Aside from my personal expenses, I have no payroll and practically no overhead. I’m able to turn down work that seems unpleasant or doesn’t jibe with my philosophical predilections, even when the work would pay very well. If I have a good few months and feel like not taking on any more projects for a while, I can do so. I can spend as much time as I’d like working pro bono on free software. On the flip side, when someone approaches with a project that sounds fun but might not pay well, I can take it, guilt-free.

Flying solo also means that I’m constantly being integrated in and out of new teams and projects. I’m constantly exposed to new workflows, new tools, new technologies, new ideas. Sometimes the rootlessness feels lonely, but it can also be exhilarating.

It’s not so bad being a loner.

9 thoughts on “The pleasure of being a lone wolf

    1. Boone Gorges Post author

      the commute is nice also

      Bingo! Though, to be fair, lots of companies are distributed.

      gotta love the sense of accomplishment building things completely end to end from scratch

      Yeah, good call. This is one of ways in which small- to medium-sized projects are appealing.

      Reply
  1. Aram Zucker-Scharff (@Chronotope)

    Being exposed to a variety of workflows and dev tools as a freelancer has been hugely useful for me too. I rarely work with someone without taking something back to improve my future work. I haven’t been doing it long enough to get the same feeling of sustainability though. The balances are not always easy or apparent.

    I wonder if there isn’t somewhere in-between, I’ve been seeing stuff like that lately. I wonder if that might be the optimal model, companies of loosely affiliated freelancers who get tagged in and out of projects as needed, work as freelancers, get paid like freelancers, can go off and do their own projects or contracts, but still have access to the greater support, knowledge and camaraderie of the team. Oh, and the option to pay in for health insurance benefits that come with working in a company

    I’ve been thinking about it a lot as the ‘gig economy’ becomes more apparent. For a long time companies have been built and oriented around management structures, but as more people find themselves in and out of a company for a single project or set of goals, it might make more sense to build companies around collaborative skill sets and to build those companies with mechanisms to hook in people and other companies or services on an as needed basis.

    Reply
    1. Boone Gorges Post author

      Hey Aram – Really interesting thoughts. On one hand, I love the idea of a loose affiliation of freelancers, especially for the camaraderie and the potential to take on bigger/more varied projects. However, once you start working on these large projects – or once you start introducing the idea of “tagg[ing] in and out of projects as needed” – you need to introduce a management layer (the person doing the tagging). You immediately lose some of your flexibility, and you introduce a quasi-boss where before there was none.

      Thinking about this setup in terms of the “gig economy” is as troubling as it is heartening. Possibly the best thing about joining a company is the knowledge that you get a regular paycheck; when you get hired, you are in effect trading some of your freedom for this luxury. (Hobbes!) But the loose federation model suggests a situation where you give up some of that freedom without getting a regular paycheck in return.

      I’m not saying it’s necessarily a bad trade-off – just that it is is a trade-off.

      Reply
  2. Andreas Karsten

    I sometimes really miss being a lone wolf. But this, by Aram,

    I wonder if that might be the optimal model, companies of loosely affiliated freelancers who get tagged in and out of projects as needed, work as freelancers, get paid like freelancers, can go off and do their own projects or contracts, but still have access to the greater support, knowledge and camaraderie of the team.

    is pretty much how we are working with the (nerdy) freelancers in our team. Also because those who appreciate lonely-and-wolfiness walk away if you try to pin them down too hard & too fast.

    Reply
    1. Boone Gorges Post author

      Andreas – You mean like this? https://www.youtube.com/watch?v=vJtf7R_oVaw

      See my reply to Aram for some of my thoughts on this. The folks who are working on your projects are lucky because they’re working for you – a legitimately decent guy, working on a worthwhile project, who holds other people’s needs and wants in high esteem. Unfortunately, I think that many clients aren’t necessarily like this. (Not that it’s their job to care about the well-being of their contractors. That’s the whole point of a contractor – you don’t have to.) It’d be cool to figure out an affiliate system that connected freelancers with good people like you, while sheltering them somewhat from the risk of the *other* kind of client.

      Reply
  3. Andreas Karsten

    Interestingly, I have never thought about this as a risk, really:

    “the loose federation model suggests a situation where you give up some of that freedom without getting a regular paycheck in return.”

    It would be stupid on both ends – as a company, you gain a quickly unhappy freelancer, as a freelancer, you gain more complications than security – but I indeed might be too naïve…

    By loosely associating a freelancer I (as an employer) get something extremely valuable: experience from other projects, solutions to problems I don’t yet have but may well encounter, in other words a much broader range of learning, something I have to seriously invest in as an organisation for full-time employees.

    I am happy every time I can work with somone who enjoys their freedom and believes in their own independence – it’s rare enough as a conviction over here. It doesn’t work for all positions, and with all people, but when it works, it’s just perfect.

    Reply

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