Ask HN: Advice for a Generalist Going Solo? | Hacker News Reader

Ask HN: Advice for a Generalist Going Solo?

108 pointspaulette44960 comments

I'm 50. I started my career as a developer but my role over the past 15 years has morphed into a professional generalist in small (<10 people) financial firms. I have responsibility for all non-revenue activities (legal, accounting, audit, operations, regulatory, etc) so most of the team can focus on revenue.

I've decided to move to another country and that means I'll have to leave this job. As much as I have enjoyed it, I would like to go solo / entrepreneurial. Being a generalist with no specific skills, seems to be both an asset and a liability in such a transition

Has anyone made similar career changes with advice to share?

EDIT - Great responses so far. I'm particularly interested in hearing from anyone that went from generalist to a completely different direction/field. Not just contracting their generalism or specializing within one of their general fields. Thanks!

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When I was younger I tried the generalist consultant thing. Did a bunch of interesting jobs and patted myself on the back for being able to tackle so many different types of problems, stacks, stages of the business, etc. It actually was really fun.

To my surprise though, as I got more and more general the rates I could demand got lower and lower, even though I had all these successful projects and good references etc. I finally picked up on the fact that the only companies who would consider a generalist either didn’t know what they were doing, or couldn’t afford an expert in the specific skills they needed.

Decided to specialize in something in-demand, and life got a lot easier.

I've had mixed experience here. It REALLY depends on what you're specializing in; specialization alone doesn't cut it. Also, you can get away with being a skills generalist if you instead specialize in a field/topic/etc (IMO).

So its more about positioning, I think. How you're able to sell yourself and the skills you have.

Agree on both points, and quite possible the “small financial firms” thing the OP has been doing is a targetable niche.

"only companies who wanted a generalist either didn’t know what they were doing, or couldn’t afford an expert in the specific skills they needed." Spot on.

I went down the same path, and came to the same conclusion. Most of the time you don't even have to learn that many new skills to "specialize", you can just change the messaging and positioning on your website/resume/conversations with future clients.

I once met a programmer who, while broadly skilled, had looked around and seen that .NET programmers were in high demand: "So, I became a .NET programmer!", and things worked out well for him.

That observation has resonated in my head since.

I've been lucky in that respect. A lot of start-up financial firms in my sector are founded by traders looking to go our on their own. The last thing they want to do is deal with "back office" matters so it is one space where generalism pays a premium.

I've done well and been paid well but I'm moving away from generalism for other reasons.

That almost sounds like a productise-able thing? What is the sector ? Is there a "backend in a box" possible ?

What did you specialize in?

Javascript.

Be an expert with the ability to generalize in your back pocket when you need to. A generalist skill set does not mean you have to do generalist jobs either.

What you say is 100% true. It's a bit sad nonetheless, companies often hire specialists when what they really need is a great generalist. Few orgs understand their own needs very well.

It's also a difficult exercise to the generalist-minded, to market oneself as a specialist. One must adopt a very reductive view of one's own skills of experiences. "From now on, I'll just be a Python programmer who specializes in backend systems for the medical industry" is hard to internalize.

What fields/tech stacks would you recommend to specialize on? I have nearly a decade of experience in programming but I'll probably specialize just to stay in-demand.

I've been a generalist in tech and a contractor, so my experience, while not directly applicable, may be helpful to you.

In my mind, being a solopreneur is all about lead flow; that's the toughest part for me. I leaned heavily on my network as they knew the quality of my work and I didn't have to sell them much. I'd start reaching out to everyone who you have worked with in the past decade and letting them know you are looking. My favorite phrasing, which doesn't put past contacts on the spot, is "I'm looking to do XYZ. Do you know anyone who is looking for such help?"

I'd go looking for work 6-8 weeks before my contract ended (I tended to have 1-2 at a time).

You could also look at productized services, though I didn't do much of that. More on that here: https://neilpatel.com/blog/productized-services/ Maybe a 'startup package' which handles most of the toil to get an org set up?

Every startup I've ever spent any time at has needed help on the business administration side. Nobody likes that paperwork and the packaged services are incomplete. Needs an experienced human.

Yes, at $CURJOB both the founder and CEO (different people) spend plenty of time on the biz admin side, even with part time accounting and CFO folks to help.

I think you are right re: productized services. I don't want to go from employed generalist to contractor generalist. I've been an IT contractor earlier in my career and I felt it was just another form of employment, with certain advantages and disadvantages (ymmv). I had been thinking of pivoting out of generalism completely but perhaps productizing some aspect of what I have done/learned is worth exploring. Thanks

> I don't want to go from employed generalist to contractor generalist.

Ah, then you'll want to specialize. I've seen this work for many folks and I did to some extent (definitely got egg on my face because I thought "<new tech X> can't be hard to learn, I'll just accept this contract and pick it up". Narrator: <new tech X> was indeed hard to learn).

If you are looking to specialize, I can't recommend Amy Hoy's work enough: https://stackingthebricks.com/ The team there has a ton of articles, books and whatnot to help you find the focus you need.

One of the most overlooked strategies I've found for lining up new work is to be always helping others find gigs when they need them. This is a great long and short game (and it feels good). If you help someone land a dream job and they need a pinch hitter down the line, it can be a great stepping stone from small businesses to top tier clients.

In the short term, helping friends and people you meet find their dream jobs almost always pays off in a good friendship, intros, and occasionally sub-market help when those individuals are looking to broaden their skills and you want to take a risk / increase capacity. It can feel scary to add payables, but it's much easier to sell when you can confidently go into a meeting and say: I/ we've never done that before, but we have a really healthy network to pull fresh devs from, it mitigates very legit concerns of on the job training. Any savvy client that's going to challenge you to bring your A game will sniff out being oversold from your first conversation.

Also, don't overstay. Especially right now, with startups having real concerns about their ability to raise, getting 2 projects with a few months in gap from the same client can be a great way for you to have a natural renegotiation about rates, work-style, etc without running the risk of bikeshedding, which is bad for everyone (your skills will suffer, making it harder to write clean, short proposals). This habit allows you time to make sure you've got good deal-flow and that you're showcasing work regularly, and you stay relevant.

Been a generalist self-employed consultant (non-I.T.) for 20 years. Some suggestions:

* To do well, you'll need to learn how to consult -- your skill set and the skill set of consulting are two very different things.

* Even as a generalist, you need to figure out what you can do better than anyone else. That might be a specific skill or it might be particularly compelling packaging of your skills but, either way, you have to stand out. If you don't, you're competing on price and client stupidity, and both are a good way to be frustrated and poor.

* Have rules and stick to them. Mine were always: No clients who had never hired a consulting solution in my space before, because the training-wheels stage takes time. And no clients who were so small that the owner was my primary point of contact -- when you're spending your contact's butter-and-egg money, it makes for messier engagements.

* Learn to sell. You'll want to believe that you can do in on social media, do it with the strength of your existing network, blah, blah, blah. Nope -- all of those things will eventually fail you and you won't have developed the sales muscle to get through the dip. You have to get good at aggregating and then talking to strangers. convincing them of your value. Related: Set your rate high enough that you are living good on 1,000 hours of billable work a year or less. That gives you a lot of time to market.

* There's unreasonable value in being easy to work with. Fixed fees. One-line invoices. Charging a high-enough rate that it's easy to say yes to minor scope tweaks without having to change the contract. Stuff like that stands out.

My advice is, watch your costs. When you leave paying work it’s easy to think the slug you’ve got in the bank will last a while.

But traction will take 2-3x longer than you think, and an unexpected stream of “one-offs” will eat your runway.

So be extremely conservative on costs from the very beginning.

Question - is there a name for the role that is responsible for "all non-revenue activities (legal, accounting, audit, operations, regulatory, etc)"?

Right now I'm doing all of that at our startup and would love to find an individual with this exact skillset so that I can focus more on hiring, product, and growth.

> is there a name for the role that is responsible for "all non-revenue activities (legal, accounting, audit, operations, regulatory, etc)"?

Overworked? I'm not sure legal and accounting are things that one can just "do".

I suppose maybe just "operations".

Chief Operating Officer in my case though I have other catch-all titles too. lol.

I'm doing exactly that + IT + compliance and a bit of revenue generation (marketing). The role is called COO.

Corporate space has a hard time valuing generalists

Crypto space does not, the more you can do, the more value you can extract

easy to miss that this is what's happening, but private sector failed to value a skillset and another sector did not

If it’s not government, it’s private sector

^one sector failed to

you're right, it was a mixture of making a synonym for corporate while also trying to distinguish between business sectors

Sorry, how can you handle legal, accounting, etc, in a different country? Python is just python no matter where you go but obviously laws don’t work that way. How does this work?

Possible scenario: OP has gone abroad for their current job and is now returning to the country where they grew up and is familiar with all the rules, perhaps even friends back from school who became accountants, attorneys, etc.'

Great question.

Take legal for example. I spend a lot of my time working with lawyers in countries where we are setting up a vehicle / working with a client but where I am not domiciled and IANAL in any country! I decide with our management team what kind of legal structure we want, the terms, the carve-outs, the financials etc and I draft layperson's language based on that. Our (external) legal team will turn that into a 60-100 page document that is compliant with the laws of the territory in question. I will review that in excruciating detail, look for errors, edit and iterate many times until the document is good for our purposes. This really means going through every kind of scenario (defaults, bankruptcies, early termination for any reason, loss of key personnel etc etc) to make sure nothing will bite us in the butt down the road. Once the vehicle is launched, it is my job to make sure that the financial vehicle follows the rules laid out in the legal document on a day-to-day basis. By this stage, I know every clause in that legal document, usually better than the drafting lawyers because I'm the one that "lives" with the document. I can do all of that without being a lawyer or being knowledgable about the specific laws of the territory where the vehicle is based (which is not necessarily where I am domiciled) because other people bring that local knowledge to the table.

So .. while as a firm we hire outside counsel to perform our legal work, it is far from outsourced. I am heavily involved with my business knowledge and prior experience with legal documents (learned on the job), and the lawyers have their legal knowledge, prior precedence and all-important templates. And we marry the two to craft and manage our legal agreements and vehicles. I am confident I could apply that skill in any country with similar legal foundations to the US.

To be clear, I cannot think of any scenario where you would allow a non-lawyer generalist to operate without external counsel.

Compliance, contracts, and accounting are at their core pretty similar throughout the world. The details differ locally, of course. Think of it like running your Python code in different environments without the benefit of containers.

This is not just an international thing, some types of businesses need to do this on a state-by-state basis within the U.S., or even for localities like city or county. For example retail chains may have to deal with signage and parking laws that differ from town to town.

A person leading operations interacts with local subject matter experts to succeed in these areas. The structure of those interactions is pretty consistent: you tell them your business priorities, and they tell you the risks. You make business decisions based on those conversations, and then monitor for changes.

I moved to a different country and attempted to start a business. I failed, but here is what I learned:

1) Doing business in a foreign country is hard. Your two options are to target your new country or target your home country. If you target your home country, meeting with potential clients is going to be hard due to the physical distance and the time zone difference. If you target your new country, you're going to be at a disadvantage from a language and business relations perspective. Also, pretty much every country is inferior to the U.S. in terms of business development. Companies outside of the U.S. can be much more risk adverse and unlikely to do business with an upstart.

2) Getting a cofounder is really important. Moving to a different country can be lonely, and running a business can be stressful with a lot of failures. You need a partner in your business to lean on and to fill in for your weaknesses.

3) Have a good idea of your business plan before you start. You should basically have people lined up to use your product before you build anything. If you don't have that, it's likely you won't have a product people want once you build your product.

With cofounders, do you have any advice on how to make sure everyone's OK with how everyone else is contributing (especially in a remote situation)? or is it just a lot of candid communication combined with some trust?

What's most important is to have complimentary skills and shared values. Lots of clues to what sharing values can look like:

1- social cues (do they say or do things the same or different?) 2- similar goals/motivations (do you often pursue similar milestones? do their motivations match or compliment yours?) 3- similar methods/reasons (do they think in lean terms? or large strategic moves? are they abstract? or ultra practical and metric driven?)

Make sure you can trust this person and that they always try to follow through on what they say. Understand how their own perception of their own status and recognition by others affects their decision making. I'd advise to watch very closely what they do, and weight what they say (justifications, rationalizations,) very lightly.

It's important not to overthink this - You're a specialist at being you, more specifically you have a bundle of skills, some of which will be useful to people with both problems and money. All you can really do is to isolate those skills, give them a name, and offer that as a service.

Based on your original description - you are an expert in "back office" skills.

My experience has been that, atleast from a software development perspective, building and launching a product takes much longer than you would initially think. And so to be ready for two or three times as long to get off the ground. Not sure how that applies to non software entrepreneurship

For hardware, take your long estimate, and multiply it by about 3x more to arrive at a reasonable estimate for launching a hardware product. Especially if it's an electronics based product.

Specialize to catch the attention of HR/Recruiters/VPs; you are right, no one wants a generalist.

However, I find once I get in and do my specialty, I'll then generalize and flex as the project needs me. I am paid to be nice and make problems go away, above all.

> I am paid to be nice and make problems go away, above all.

Absolutely. Sometimes I’m also just paid to be „that outside guy“ who can bring in fresh ideas or change things that were set in stone just by virtue of not having a stake in internal corporate politics and not looking to take away anyone‘s cushy job.

Are you a product manager?

Nope, software engineer. But you can make a huge difference, especially as a generalist.

Going solo may only make sense if you plan to take on a number of clients.

If you're planning to work with one at a time, you can avoid the overhead and costs of running your own company by convincing desirable companies to simply hire you.

In which case you can potentially evolve your employment into your first contract, while moonlighting additional leads.

Pick a niche and become visible great at it. Make sure you have an efficient process for generating leads and new customers.

Sell yourself as a specialist consultant, invariably companies need generalists they just don't know that they do.

I'd make sure to validate the business idea while still on a paycheck. Burning your savings with no success is more and more painful as years go by. It was already painful at 33 for me :)

I'd say it's less painful as you're closer to retirement since a large portion of your earnings are coming from compounding interest.

I agree 100%. My move is 12-18 months out. I'm ready for an income drop, just not to zero.

Depends on what you want to do. Entrepreneurial as in start your own consulting company? Or starting a startup where you're (generally speaking) selling a product of some sort?

Great question. I've always felt "entrepreneurial leanings". Of my parents and siblings, I'm the only "employee". Unfortunately I've always been paid generously enough to curb those leanings. i think this is as good a time as any to test those "leanings" and reading about entrepreneurship and take a risk. Having worked for 25 years, I need to de-institutionalize my thinking and figure out what I'd like to do. It would have to be a passion project thogh because at this stage of life, that's what is going to drive me.

IMO step 1 is figuring out what kind of business you want to build.

Loved all the insights here. Especially the ones mentioned by gwbrooks. They are quite insightful for someone starting out in their career.

Focus on building a solution to a problem. Not your problem, but a paying customers defined problem.

If anyone hasn’t recommended, you should join IndieHackers.com’s community.

You’ll find people on a similar path.

There are riches in niches.

Specialize in whatever is in high demand and you will always do well.

don't try to do everything yourself

(find cofounders, or teammates/a network you can look to for the things you don't do well!)

I think the challenge for generalists would be to find other people to do things you can actually also do better than the people you can hire and live with that.

In my case, you are right. An accountant, a lawyer, a HR professional etc could each do that element of the job better than I could yet I doubt any of them could do all aspects of my job better than I do.

The question is scale. When you're a small firm that needs all these services, you cannot afford a professional in each role so you outsource all those functions to larger firms ... but you still need someone internal to have enough depth of knowledge of each field to direct and validate the specialists' work. There is absolutely no "set it and forget it" when it comes to outsourcing the professional services that keep a (heavily regulated) company ticking over.

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