I’d actually go at a different argument than generalist versus specialist, some fairly commonly heard wisdom in UK was if you were risk-tolerant you could “always make more contracting”. What you also hear is “charge more”. I would instead say to both of those things that one should seek to understand where they want to be in 5-10 years, earning what and doing what?

A lot of these threads do boil down to the few making $350 per hour, the many making $100 per hour, and both cohorts seeking to make more. I can’t actually tell you how to do that while contracting, I can tell you my story and perhaps it will help someone :-)

I pursued contract roles for a few years typically resulting in me making £100-250k gross per annum range, typically billing at £1000/day or £15-20k/month and optimizing UK tax using all the usual and perfectly legal means. That’s a good income and my family had an okay standard of living.

These roles were anything from software development to systems engineering, mostly a “make problems go away” situation - clear connection for the client to business value. I worked for everything from US startups through to UK financial services.

Before that I’d done some full-time roles with big and small companies typically in the £80-150k range. Striking out as a contractor was partly the desire to try something new and partly a particularly interesting opportunity arose.

Eventually, I ended up going back to what I’d still consider generalist roles with larger FAANG or FAANG-adjacent employers, that’s something of a “loss of freedom” versus contracting, the nature of growing a “career” with them (not the same employer necessarily, just the same set of companies).

For me, long term goals were twofold:

1. To have interesting work and problems to solve, ideally to engage with smart people;

2. To make money, lots of money, I’d like to retire at some point, and I’d like my standard of living to be high, I’d like to never really worry about money.

In outcome terms, making that jump back to FTE and “getting in the door” of FAANG, which took effort both to get in and then to excel in the new roles, it has paid off in ways where generalist consulting could never take me, I relocated, now take roles that are FAANG or FAANG-adjacent executive-level roles in “Engineering”, these involving a multi-disciplinary mix of duties — Product, Software and Program Management, the full spectrum of working out what the customer needs and what that means for the business, building that technology often with a large team, enabling the field to sell it, feedback loops to improve it.

I’ve had several years of W-2 employment in the $2-4M USD range, that’s >10x from contracting rates, achieved in <10 years and I’m on track to punch my retirement ticket around 43 years old and then only work for interest, not for money.

In my humble opinion, it is much harder to sell yourself as a contractor when applying to FTE roles (particularly those at bigger companies) and to tell the story in ways a Hiring Manager will appreciate and see your value. Therefore you really need to consider whether the “hustle life” of contracting is something you want to do through retirement, what’s it mean for you when 35+ or even 45+ and is it setting you up for the endgame you want in life?