Tattoo Advice From 6 People With Years of Hindsight

I often waffle between thinking tattoos are an insane commitment and thinking they’re no big deal at all. Over the years though, as I’ve gotten my own and watched others get theirs, a few things have solidified for me vis-a-vis permanent ink: Everyone who has tattoos feels very differently about them. Try as we might to find it, there is no consistent script for those who choose to participate. Which is to say: No one approach will speak specifically to yours.

That said, I am always curious to hear more perspectives, and since I know the stories of the young and the reckless getting tatted up against their parents’ wishes all too well, this time I sought out guidance from people a little older, a little wiser, and who have the benefit of hindsight. Below are six people who fit that bill, so scroll to read their stories and advice and then tell me yours.

Olivia Kim

Olivia, 40, is the VP of Creative Projects at Nordstrom. She got her first tattoo at 14.

What made you first want (and get) tattoos?

I got my first tattoo when I was 14! My mom had just gone out for the evening, and my sister and I decided to have a party at our house. Our friends were literally hiding in the bushes and trees and, as soon as the car left the driveway, they all came in. Then my friend, who was a senior and had a car, said that he was going to go get a tattoo. I said, “Oooh, me too!”

I never thought about it or deliberated whether or not I wanted one. I just got one. I think I’m pretty much the same now. The feeling of wanting another one, and another one, and another one never goes away. I don’t like to overthink anything. You can just wind up talking yourself out of an experience.

What about it might you have done different had you known better?

Nothing. Zero regrets. I love the really bad stick-and-pokes from my best friend Jenn that we would do on the floor of my apartment just as much as I love the beautiful super-pro ones done by amazing tattoo artists. I think you have to just get what feels right for you — not your friends, or your fave celeb crush, or something impersonal. If it’s what you want, it’s what you want.

What advice would you give to people who are thinking of getting a tattoo?

I’ve heard people say, “I’m thinking about getting a tattoo but just waiting for the right moment or the right inspiration.” But I think the fun of tattoos is the spontaneity of being in the moment and whatever you happen to be thinking of in that moment. How else do you wind up with a cupcake on your knuckle?

It’s not the most important decision in your life, so be a bit free with it. Have fun! What is the worst thing that could happen? You hate it or regret it? You can just as easily remove tattoos these days as get them.

Richard Biedul

Richard, 34, is a lawyer turned model turned art director. He got his first tattoo at 16.

What made you first get a tattoo?

Believe it or not, the rationale behind getting my first tattoo wasn’t an archetypal act of rebellion nor a desire to follow a trend. It was more of a Leonard (Guy Pearce) in Memento type scenario…

My (twin) sisters passed away when I was very young. As a teenager I was haunted by the notion of their memory fading as I grew older, especially because the memories I had of them to begin with were so limited.

I guess in the simplest terms: I made the decision to get a tattoo to ensure that I never forgot them. I hope that the permanence of the tattoo on my body will act as an eternal memorial to them and to any fading memory of them that I may or may have as I grow older.

What about your journey since has surprised you?

Over the last 18 years, some of the times and places (and ease with which) I’ve been able to get tattooed have genuinely surprised me. From house-parties in Berlin and Brooklyn to shops in London, Paris and Milan. Any time of day or night. Over breakfast, lunch or dinner: the list of strange scenarios goes on and on…

I wouldn’t change anything. I stand by all of the decisions I’ve made to get each and every one of my tattoos. Except maybe the drunken decision to get a unicorn on the back of my left arm…

Thoughts on style choice?

When people ask “Can you recommend a tattooist?” I always say yes, but caveat any suggestions based on what style of tattoo the person wants.

Stylistically, my tattoos are all done by different people from different parts of the world, but they all maintain aesthetic similarity. They probably don’t necessarily fit any one of the major tattoo styles but if I were pushed I would say they’re a mixture of traditional and stick-and-poke…

There has been a large number of people in London over recent years who having never expressed an interest in tattoos have, in the space of 12 months, covered every inch of their body in an attempt to fit an aesthetic that has taken others decades to achieve. On some people it works, on others it looks contrived. It’s like going to Supreme and buying one of everything. Owning these items doesn’t necessarily make you stylish. It just shows that you have a propensity to follow trends (and consume fashion).

Any common misconceptions you’d like to debunk?

“Does it hurt?” I get asked this quite a lot. The longest session I’ve ever had was three hours. Before I had that session I would always say: “No, not particularly.” However, post-wolf’s head, I always answer in the affirmative! But just how much depends on a person’s individual pain threshold. What is tolerable to one is intolerable to another…

Any advice for people thinking of getting a tattoo?

Tattooing, just like art, fashion and music is purely subjective; what one person likes another hates. Obviously you can appreciate the technical expertise that went into the work, but everyone should tread their own path, do some research, find a style or artist that YOU like. Don’t be influenced by your peers, sportsmen or celebrities. Take risks and most importantly…be original!

Mary Dorman

Mary, 67, is a civil rights activist attorney. She got her first tattoo when she was 55.

What made you first get a tattoo?

I believe I have always been an outlier. Since birth. I have never been afraid to be different because I simply am. On the other hand, I am a white female who looks like so many others and none of my friends have or had a tattoo. Maybe a teeny one in a hidden place. Good tattoos have always appealed to me. There was a fabulous show of them at the Drawing Center in the ’90s and I knew I had to have one. I have never regretted it for an instant. I wouldn’t have done anything differently. Now I just want to enhance it but have to find the right artist.

The surprise of my personal tattoo journey is how many people want one but are too chicken to get one.

Any advice on style choice?

If you’re going to get a tattoo, commit to it. Anyone can have a little dot that is a dolphin or a peace sign…boring. Might as well wear a temporary. That said, it doesn’t have to be huge by any means. One thing that I have noticed is how most people get a tattoo in a place that they can’t see it: shoulder blade, back, etc. I enjoy seeing mine.

BUT! My tattoo can’t be seen unless I have shorts on, as it is on my calf. As I age, I would like to get a tattoo of an octopus tentacle poking out of my collar just up my neck, but that may not be in this lifetime.

Any common misconceptions you’d like to debunk?

What cannot be debunked is that if you get a shitty tattoo, you are stuck with it or Dr. Zizmor (who advertises for tattoo removal on subway signs).

Any advice for people thinking of getting a tattoo?

Think about the image and get a true tattoo artist to draw a sketch that you can personalize even further. The tattoo has to be about you. Also — really fight making the decision when you are not sober. Some PRETTY BAD tattoos come out of spring break in Key West.

Charles Taylor

Charles, 56, is a writer. He got his first tattoo at 50.

What made you first want and get tattoos?

It was an idea I toyed with on and off over the years. What would I like? I always wanted a pin-up girl, you know, a kind of Varga girl. But, frankly, I worried what that would look like when I got older. Would it be the tattoo equivalent of the mid-life crisis sports car? I don’t think aging has to mean dullness. I see how reluctant men much younger than I am are to try anything that isn’t run-of-the-mill dull, and it just makes me despair for my entire gender. There is nothing more boring than the sartorial habits of the average American man. On the other hand, you don’t want to look like an ass.

The decision when I made it was simple. My mom died. Six days before I turned 50. I decided I wanted her name tattooed on my left shoulder. I was so marked by her death that marking my flesh seemed of very little consequence.

I asked some of my students where they got their ink. And the same name, NY Adorned on 2nd Ave, kept coming up. I went in on a Saturday and got her name and middle name, Eva Lorraine, in simple black script on my left shoulder. I remember being strangely proud when, after he was done, the tattooist said to me, “Wow! You’re a bleeder.” It felt right that I had bled for the honor of having my mom’s name engraved on me.

My dad was, at first, a little taken aback. But he understood why I did it, and he came to like the tattoo. He even kidded me, “When are you going to get my name?” I did this past April the week after he died, on the opposite shoulder, in the same script, his first and middle name, Charles Henry.

What about your tattoo journey has surprised you?

A few weeks back, I was moving boxes after hours at my part-time job and was wearing a sleeveless undershirt. My boss, who is covered in tattoos, looked at the script on my back and said, “Those look so sick, Charley.” It was a compliment from someone who knows about the artform and who means what he says. It meant the world. There are only a few more names of people around me I love who I would find a place for on my back, but because I love them I’m hoping I go before them. I have toyed with the idea of getting a quote written on my side, but I’m afraid the particular quote I have in mind might be an inadvertent curse rather than the point of pride I would intend it to be. And no, I won’t tell you what it is.

Are you pro or anti-“trendy” tattoos?

Completely against trendy tattoos. It’s not like the thing you buy at H&M to wear for a season.

Any common misconceptions you’d like to debunk?

Well, they are so common now that we can no longer say, “Think of what will happen when you try to get a job.” Cops have sleeves now. That said, like any style that becomes common, not everyone wears them well. I work a part-time job with guys in their 30s who are covered in tattoos and they’ve thought them out, who they wanted to tattoo them, how each would work with each other. I recently met a woman who is having an entire bodysuit done. I saw a photo and it was ravishing: completely thought out in terms of her whole body. The worst thing to me is someone who looks like they are wearing all their clothes at once. Since mine are on my back, I forget about them for weeks at a time.

Any advice for people who are thinking of getting a tattoo?

Do it sober. Put thought into it. Think of what size you want. Will it be visible or not to the outside world and if it is, how will it go with what you wear in your everyday life?

Christie Terranova

Christie, 34 is a hairdresser at Common Good Salon. She got her first tattoo at 18. (“It was a butterfly, because duh.”)

What made you first want tattoos?

I’ve liked tattoos ever since I knew what they were. Not much has changed in that department. I’m still collecting and like to get tattooed when I travel.

Any advice on style choice?

Well, it’s no surprise, good art costs money. When you are young, it’s hard to spend a lot because you don’t have a lot, but hopefully when you get older, you get nicer pieces. As far as tattoo trends, I couldn’t care less about what other people do to their bodies as far as modification. It’s not my place to judge either way.

Any common misconceptions you’d like to debunk?

Where we live, in New York, there’s not much to debunk…we live in a very liberal place. As far as other places, located in the US or outside, being a heavily-tattooed woman is considered strange. But the world will come around. When people ask about them, my usual response is: “I just like them.” It’s that simple.

Any advice for people who are thinking of getting a tattoo?

You definitely get what you pay for. Tattoos are expensive. I know it sounds redundant to say, but they’re permanent. Pay the money. It’s worth it. Also, above all, the people who are tattooing are artists. They are expensive because they don’t get paid time off or health insurance. You’re helping with that. It’s not cool to try to lowball someone. And finally, opinions are like assholes. Everyone has one. So, do what you want. And live your life.

Amanda Wachob

Amanda is an artist and tattoo artist working in New York, New York.

What made you first want tattoos?

I never expected that I would be a tattoo artist, and had never really thought about getting tattoos prior! I got my first tattoo during my apprenticeship; I picked a design from a piece of antique sheet music.

What about your journey has surprised you?

I think what’s really surprised me is how obsessed I am with everything about tattooing. I didn’t expect to fall so completely in love with it. It’s truly my passion and time disappears when I’m working…I feel really lucky for that.

Any common misconceptions you’d like to debunk?

Get the style of tattoo that you want regardless of that whole “longevity” thing.  Your body starts breaking down the tattoo ink as soon as it goes into your skin no matter the color or style or application, and all tattoos will age and need a touchup eventually. We are here for such a short time on this planet, so decorate yourself however you want and enjoy.

Any advice for people who are thinking of getting a tattoo?

Definitely research your artist, and have them make something unique just for you. It’s never good to ask a tattoo artist to copy someone else’s work, it’s best to seek out that artist directly, even if it means traveling to them or waiting for awhile before you can get something.

Illustrations by Eloise Weiss.

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  • Elena Bergamin

    You guys are magic, I really have no idea how you can manage to get the perfect article for whatever I’m going through at just the right time! I am getting my first tattoo in two days and this advice is so so welcome (and feels meant to be!)

    • Good luck and enjoy!!

      • Elena Bergamin

        Thank you, I’m slightly freaking out about the pain because I’m basically an 8 year old, but I do get Brazilians on a monthly basis without any problems and a lot of people have told me those are worse, so hopefully I’ll survive haha

        • Katie Lucchesi

          Waxing is def worse than getting a tattoo.

    • Lauryn P.C

      Haha Elena, I so feel this too.

  • Autumn

    I have five tattoos and I love all of them. The first one I got when I was 18 (because I could) and wouldn’t get it now, but I also would never get it removed. All of my tattoos remind of where and who I was at that point in time. They’re nice little mementos.

    • that’s the same reason i like mine! they’re just kind of all these past lives i carry around on my body and i feel fondly toward them

    • Amelia

      that’s EXACTLY my feelings too. I got my first one at 18 and I wouldn’t get it now, but I don’t think I would ever want it gone. helps that it’s on my back and I forget its there.

    • peenerbambina

      I always call mine bookmarks. I can remember who I was when I got them done, and even though they are all a bit disjointed from each other I wouldn’t change anything. Even the 90’s tramp stamp fairy.

      • Autumn

        “Bookmarks” – I love that! Yes, mine are disjointed too and I got many of them after big life events (turning 21, graduating college) so they’re definitely bookmarks.

    • Lauryn P.C

      I have the very same opinion! Two of mine that I got between 18-20 I look at now and would never get now, but the thought of having them removed doesn’t really digest well for me either. I don’t HATE them enough to go through that pain. And I also agree that they are a snapshot of who I (we) were at a different time in life. So glad to hear another person with the same perspective!

  • Aleda Johnson

    I think the best thing about real tattoo people is how little they judge others. Totally experiential evidence here, but people with tattoos are usually some of the nicest, most open minded people I’ve ever met.

  • I am currently planning with my sisters to get matching ones that honour our relationships, based around the name of our childhood dog Clover. I never thought I’d get a tattoo or had any particular interest, but it’s surprised me how right this feels to do.
    A really perfectly timed article that has encouraged me to just go for it – thank you!

  • Cynthia Schoonover

    Good advice. I got my first tattoo last summer. It’s a pair of angel wings on the inside of my right leg in memory of my mom, dad, and brother. I had been thinking about it since my brother passed away 7 years ago, and after my mom passed away last year, I definitely did it. I knew what I wanted, and the artist did an excellent job. By the way, I am 63, so it is never too late. I’ve never seen any point in having a tattoo I couldn’t see.

  • ladle

    I have been thinking about tattoos for a long time. I don’t want one until I know exactly what I want, I have enough money for it and find someone I trust to do it, because I feel like I am a big baby when it comes to pain and needles, so if I’m going to do that it better be quality work. This is also the reason why I don’t know the placement yet.
    I currently have the ‘what I want’ question solved, but nothing else, so I’m waiting.

  • i am shocked i haven’t regretted my 9 tattoos yet, considering 8 of the 9 were basically last minute decisions. awesome illustrations and interviews!!! excuse me while i go get 15 more…

  • Amelia

    “The feeling of wanting another one, and another one, and another one never goes away.”


    • Jessica

      So feeling this.

  • Kate

    My office is in Chelsea, and while the people who work here are, as you might expect, on the liberal side politically, you can’t just rock your tattoos. There are still plenty of industries where tattoos are not accepted. I would never show mine at work, so the idea that it’s so common place nobody cares anymore is just like, really funny to me. Appearance still matters very much.

    • Kate

      This was a good piece, I just think THAT is the most common misconception I guess. That they’re no big deal now.

      • Sylvie

        I really like your comment, but ALSO I like your hyperbole and a half profile picture 🙂

  • Jam Jam

    I enjoyed this, especially the lightheartedness of the first woman.
    I’m curious if any of these people investigated and considered the historical context of tattooing, if it factored into their decisions. All fashion builds on what came before, so to not acknowledge the history of tattooing is bizarre, especially since we try to be sensitive to cultural appropriation these days.
    Another interesting piece is the insider/outsider element – growing up, I could look at someone’s tattoo and know their background, gang affiliation, religion. Now, tattoos are more about uniqueness, as opposed to belonging. Anyway – interesting stuff!

  • starfizz

    I’ve loved the artistry of tattoos for a while, and I’ve followed some tattoo artists on instagram for a few years, and I even work in an industry where it’d be ok to have tattoos, but I’m afraid of both needles and permanence, so…I think it’s not for me. At least not yet.

  • PlaidandPrejudice

    I have a flock of 18 birds (no particular meaning) & an anchor with a rainbow striped banner that is a homage to my roller derby team on my back. I also have the Tree of Gondor from Lord of the Rings on my arm. Next up is a Lisa Frank style unicorn. I love my tattoos. No regrets here. The only advice is give would be to keep them in easily hidden places if you work in a professional office or career.

  • I’ve had tattoos for a few years now but it feels like I can’t remember my life without them, they’re a part of me now. At first it was strange but after a few weeks I got very used to them. I hope I don’t end up regretting them when I’m older, but reading this made me feel like I won’t. I am surprised about how many of these people talk about getting last minute ones that they don’t put too much thought into though. In my city it’s common to have to wait months and months for your appointment, so you kind of have to put thought into them.

  • Gene Day

    I wish to spread the news that the needle of a tattoo artist feels NOTHING WHATSOEVER like that of your doctor or nurse practitioner. For me (and everyone is somewhat different) lines feel like a loooong scratch, and shading is more uncomfortable and a building pressure (if you want a watercolour style, be aware).

  • Jackie

    Not as much a fan of tattoo as I am of these ILLUSTRATIONS. MR has been killing it on the visuals front lately. I used to come for the written content (90%) and then the visuals caught up the remaining 10% of my interest, but moving towards 50/50 now!!

    • Kimbones

      Snap. I thought this was a lovely and original way of showing and talking about tattoos.

  • Naomi du Plessis

    Loved this article! I’ve got a bunch of tattoos already, but starting my half-sleeve in the new year. SUPER excited.
    The thing that’s most annoying about having tattoos though is when people constantly ask you “So what’s the meaning behind it?”. Ummmm, I liked it so I got it. Simple as that. I have a few random pieces, but those are the ones I love most <3

    • I make up meanings for my tattoos! It’s GREAT fun. Highly recommend.

  • Camila Restrepo

    I got my first (and only one so far) about 5 years ago when two of my cats died within months of each other. Even thought it’s a super simple design in the inside of my left wrist, I don’t regret at all. It has been a point of conversation during many trips and funnily enough, I feel like I love it even more now than when I was 19. Ever since I got that one (which was very spur of the moment), I been wanting another one and another and another one. In the past month, I have finally decided it’s about f**** time and hopefully within the next week or so, I will get my second one. 😀 Right wrist, here I come!

  • awesome illustrations !
    Haley, what are your tattoos ?

  • elpug

    I love tattoos! I see mine and the money I put in them as an investment in self love. They aren’t for everyone but they are for me! They represent my struggles, my passions, and who I was at each ink session.

  • Kimbones

    I’ve just booked in for my first tattoo in January, after years of looking at artists and gradually falling in love with the work of one in particular. I’ve had a shitty year, really shitty, and I am so excited to wrestle back some control and finally have some control over my body. It’s going to be pretty big though, and I of course I keep thinking – what will I think in a few years? It’s a well thought through design but it won’t be for everyone – but no tattoo would be. But I want to be a badass grandmother. This article was timely for me and helped make me feel like I am absolutely doing the right thing. I’m so excited! Skeletons! Ropes! Medieval plague creatures! Bring em on. PS I loved Charles Taylor’s story in particular. It was very moving – thank you for sharing, Charles.

    • sorry you’ve had such a shitty year.. getting tattooed really helps with that tho! at least I think so 🙂 also, your design sounds AWESOME. can you describe it in more detail?
      I have the dancing skeletons from the Nuremberg chronicles on my back, so medieval weird shit is def my thing too!

      • Kimbones

        Aw, thank you. Redundancy is no fun at all I have to say. Also well YOUR tattoo sounds amazing! My artist is Ant the Elder – I think you’d love his work! He is designing me a piece for my upper arm, integrating a rope and a particular knot I like, and I’ve also requested some medieval guys/skeletons, but I’m trusting him with everything. I really like everything he does, so I’m sure I’ll love it! Although preparing myself for other people to find it a bit weird and to feel like they have to comment.

        • That guy’s work is awesome! I think giving artists (almost) free reign results in the best outcomes, so I’m sure it’s going to be great 🙂
          as far as comments go, my go to has been to vehemently agree. so for instance, when someone says: ‘Oh, that’s a bit morbid and weird’ I grin like an idiot and say “Yes! Isn’t it?!’
          the confusion is a sight to behold

  • HannaEE

    I have 14 tattoos and Christie’s “You definitely get what you pay for.” resonates with me most. I definitely have tattoos that don’t look great anymore because the artist wasn’t the best, but he was cheaper. And also don’t say yes to a design you don’t love! Some people, like me, are afraid to change an artists drawing. DON’T!!! I’ve learned that lesson.

    ALSO, I work in a law firm and am always interested in reading articles about dressing for the workplace when you have tattoos, especially in the summertime.

    • I FEEL you on the dressing for workplace. I can let my tattoos out in the office, but when I’m in the field, I have to cover up. My summer go to is camis or tanks with a nice blazer/jacket so I’m covered but not sweating. I have tattoos on my forearms so I can’t get by with a button up and rolling the sleeves.

      • HannaEE

        I guess the layer idea is always good cause you can be in your cami/tank until you’re on site! Mine are on my legs and I’m constantly jealous of girls in cute dresses on hot days 🙁

  • Jamie

    I’ve wanted a tattoo from Amanda Wachob for YEARS. Wow. So cool to see her perspective here.

  • mlc

    looking for a recommendation of good tattoo artists/shops in NYC – getting my second one soon! Thanksss!!!

  • Samantha s

    Loved this! 2 questions for the group – 1) I want a tattoo, but I do keloid quite badly. I read that I can still get tattoos, but I just need to go to an artist who knows how to manage keloiding. Anyone with personal experience??? I feel like anecdotal evidence that it is ok to get a tattoo even if you keloid would make me feel better. 2) Are there any good forums/websites for discovering tattoo artists? Or do people just google search and go from there?

    • I keloid, too! I’m not sure how bad it is compared to other people, but most of my scars are raised and bumpy, and I have a ~1″ long patch of bumps on my back from what should’ve been a VERY minor biopsy about 10 years ago. I have 2 tattoos, though, (just got my second this past weekend!) and haven’t had any issues. I’d still definitely mention it to the artist you go to, especially if you’re planning on a bigger tattoo! I’m sure they can give you much more guidance than my anecdotal evidence 🙂

  • Mari

    I regret my tattoos so much and feel like whenever I say it out loud people get so uncomfortable, if feels like a taboo. I still likes tattoos and even flirted with the idea of getting new ones, but I don’t like the ones I already have at all. I don’t like the designs anymore and don’t like it when people bring them up. I have a large one on my arm that’s always showing. I regretted it so fast, I went to the dermatologist a week after I hade it made and cryed so much. She told me to try to accept it before I did something else, but I never did. When people compliment it, I don’t believe them 🙁 Tattoo removals are not simple, they’re painful and very expensive. I have a hard time accepting that no one else seems to feel the way I do, I’m ashamed to admit it.

    • belle

      Have you spoken to an artist about working on altering or covering up your tattoos? I’ve seen a lot of amazing work done on top of older, unwanted designs. When I think back to the tattoos I wanted when I was a teen, they are not the same as I would want now. But that doesn’t mean that older tattoos are ugly or embarrassing. I’m willing to bet that when people comment, it’s because they DO like yours, and of course you can always just tell people that they aren’t what you’d pick today but you remember that time in your life fondly (or whatever the case may be). People get it.

  • leilanigl

    I have been following Amanda Wachobs art for years now ahhhhhhhhh. (Someday. Soon, I hope.)

  • dutchie

    As someone with almost 20 years since my first tattoo, and who has tried to have some of them removed, I have to say: the advice from the first interviewee is pretty terrible IMO. Tattoos can end up having worse consequences than just not liking it– it can end up affecting your professional life, so it’s good to keep that in mind. Also, tattoos are NOT easy to get rid of. It costs a *lot* more to remove them than get them, takes much longer, is way more painful, and is often not terribly effective in the end. These are things to consider when making your decision.