Planning on leaving the hair club when my contract is up and going it on my own and feel a bit overwhelmed.

I found choosing a hair color from a hair sample set really difficult. I felt like there were a few options that were close to my color that I couldn't see any difference in. Yet not one of them seem to match perfectly. Someone said that while I don't have any noticeable grey in my dark brown hair, I have some small amount of hair starting to lose pigment which makes my hair not all completely one color. But it's not very noticeable unless you really examine it closely. That freaked me out because losing my hair was bad but I never thought I would start going grey until much later in life.

I read that I can take a hair sample but I don't see how I can gouge a clump of my own hair out of the horseshoe shaped real hair. I don't see how people do that. My hair is about 2.5 inches.
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how important is it to match color exactly? Any recommendations? Hair club taught me nothing.

Are you meaning hair color for your real hair or picking a color to order for your hair piece?

Picking a color for ordering a piece. I'm researching now as I have several months to go on my HC contract. I borrowed a standard Hair color sample ring and tried to match my own and had a difficult time. Some of the samples looked the exact same to me, but none seemed to match my hair exactly. I therefore want to take a sample but don't know where or how to cut without leaving a hole in my real hair that can be seen. Since I'm wearing a crappy system now from HC, maybe I can cut an inch in the back near where the system attaches hoping the missing hair won't be noticeable if the system covers that part in the blending. I don't know what others do.

The hair system your wearing now surely that's a good color match if so why don't you take a sample from that. Of take some from when you have a new piece cut in. you could always go for a slightly lighter shade and color the piece and your own hair to match.

Not all suppliers use the same colour rings, codes and charts.

You are far better to take samples from as many parts of your head as possible and send them to your supplier labelled.
So a sample from as near to your face, one from the side and another from the back.

As Mickeyblueyes has suggested, if you're happy with the colour match of your current system, then supply a sample from that for the top of your head.

Your natural hair may be made up of several colours, not just one colour defined on a colour ring.
Factories then use microscopes to study the hair colour variances and hopefully provide you with the best match & blend.

My current HC system color was off to start with. They just said I think your a brown ash and made the system from that. I didn't know enough at the time to know what I was doing. Besides the system was oxidized and colored and again I think it's off. I don't dye my own hair.

So how do I take samples without having a noticeable gouge in my hair that others can see?

You grow it.

Growing my hair beyond what would look normal for my current HC system? Am I obsessing over something stupid?

thanks for your input, I have a lot to learn.

Its a short term anomaly for a long term gain.
You only ever have to do it once.
I wouldn't make too big a deal about it if I were you.
As they say, you can't make an omelette without cracking some eggs.

I think you've been 'institutionalised' by HC and taking control of your own results seems more of a challenge than it actually is.

Ever thought about just dying your the hair of your system??

I haven't transitioned yet but have been using a concealer darker than my hair..comb it in and then spray with some hairspray and it gives me a darker color all around .. I like it better than my natural hair color.. its kind of a 1B..

So when i switch over im gonna probably hit the sides/back with 1B and go with a 1B topper because i reallly like the color.