Advice for a Generalist Going Solo?

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 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?

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.

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

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?

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.

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

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.

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.

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 :)

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?

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