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Gray Omeasoo

Gray Omeasoo

Creative writer, authentic life-story teller, photographer, film-maker, journalist. Passionate about Mental Wellness.

How I Ended Up On The Streets…Busking

9 min readSep 21, 2025
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September 21, 2025 (14:20)

First of all, I would like to apologize for the wild blog title on this one. In my defense, it came too naturally that I felt inclined to put it in as authentically as possible. (disclaimer: this blog is unedited, like. I didn’t even re-read it).

Welcome back to the blog! I am a singer/songwriter, first-year journalism student in Halifax, and someone who should be under supervision most of the time (that’s a story for another time, however, if you’re curious about that, go check out my recent vlog on accidentally visiting Citadel Hill @AmberGrayMedia on youtube!). As the title does imply, (not the streets part) I have started busking! I will go over how over the 3 times I’ve done it, how I started, where I am right now, and what I am hoping for in the future.

Naturally, as a college first-year student making friends, you start to realize that you are truly your own enemy–it is so bad that you may start to wonder what thief got into your wallet… it’s you and your impulsivity! :D Surprise! Anyways, so you start by looking for a job but forget you have just moved across the country and, therefore, you have no small businesses to casually chat up nor a resume that looks promising and reliable. Immediately, you start to go, well, I guess this is it, can’t even get home–of course, I am being dramatic.. I hope you can get home.

You could assume that that was me, except for all of the dramatic bits, because I would like to think I am pretty reasonable and I am fortunate to say money was not too much of a concern for me. Nonetheless, lest we forget where I am going with this, I was walking Halifax’s waterfront with some friends near the late evening, it was a casual walk to escape the terrible warm dorm rooms. Along the waterfront, I would notice all these buskers on the side of the walkways playing all sorts of instruments; many were guitar players, others piano, others had interesting instruments I did not know the name of. In my mind, I was thinking, okay sweet, so this is a possibility. (I have always wanted to start busking and always craved a city life. When growing up in small towns, you really crave a change and once you enter that change, doors just open for you; for me, this door was a public performance–because it is strangers instead of that random guy who worked with your mother years ago that watched you grow up on facebook).

How did I begin busking, then?

I started cautiously, though I do usually throw that to the wind. I knew I had to take into account my own safety and my guitar’s safety on this journey that unfortunately included the law, public, and transit. Though I was tempted to just go for it, I first did a lot of research on how to go about this. Turns out, in Halifax, you don’t need a busking license on the Waterfront–this was great news. I then researched locals who have started busking years ago, mostly looking for first-time advice on how to actually start because I was very hesitant yet so eager. What I found was that there is a specific place to busk, from point A to point B along the waterfront; there are also a lot of businesses and restaurants along the waterfront that have full rights to telling you to leave along with security; there are specific areas for amplified busking–for mics, amps, etc.; and there are safety concerns in the matters of your earnings (which in Halifax, the policy is to not accept ANY transactions, but donations can be accepted–don’t be a beggar now).

After reading all of the warnings and precautions ahead of me, I said screw it and didn’t follow any of them! (I did, I am scared of the law). I got some friends, went down in the late evening, rode the first bus with my guitar, walked down to the waterfront with it, and proceeded to walk back and forth along the waterfront with a sense of dread. I had forgotten what the waterfront looked like and the locations in my mind did not align with what I was currently looking at.. where do I go? My friends are stuck following a blind man at this rate and that pressure is onto me along with the public seeing a giant case by my side. I am asking for attention, getting it, but not ready for it.

Eventually, we were able to find a place just a little ways off of the heavy-traffic walkway. I can really only thank my friends for this commitment since if I were alone, I am sure to have frozen and gone back to the bus.. or wouldn’t have been able to leave the university grounds with it. However, I did find a place (it is now the same place I go to every time if I can help it) and it is right next to the Cow’s ice cream place. Strategically, what led me to that spot was avoiding other buskers to be polite, avoiding restaurants and their music, avoiding apartment buildings, and finding somewhere with constant movement–a place between a walker’s point-a and point-b.

Cow’s is arguably a really great spot to busk, it has a multitude of benches around the area, a small part area, and ice cream! Cow’s also has their window open on the side that I busk at. So, I have had many instances where passerbys see me, stay a while, and I see them go, enter Cow’s, and come out with change for me. I also have many listeners that sit on the benches near my case and listen in; sometimes there are boats that pull in and just stay by the shore for a while too. Actually, today, I had my first instance of a “regular” who said she works on the harbor hopper and ALWAYS sees me–meaning she’s seen me all three times now. It was really sweet because she admitted she never had cash when she heard me but finally had some today and gave me a stack of USD $1 bills. Today, there were also a lot of children who forced their parents to listen, which makes me feel like a consumerism ad–like how they put kids’ stuff at the bottom because kids are likely to scream and cry if their parent says no? Very manipulative, fortunately, I think I just debunked my own thoughts.

What have I noticed since starting?

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That I am terrible at playing guitar. Here are my excuse: it is too loud to tune my guitar so its out of tune, and its a 12-string of course so more strings out of tune the merrier–its a cacophony. Now, I know I can play guitar and I am a good enough singer, hence my confidence in starting, but playing and realizing you only have so little to give, it really feels like you’re an imposter when someone tips you. For example, I have a VERY minimal set list of say 6 songs, this is pathetic. Ideally, a good busker can play up to 2 hours without a repeated song, realistically, I play my 6 songs on repeat really slowly with double choruses because I chose a high-traffic area where I have new listeners every song; unless there’s Dave who sits down with his ice cream and DOES NOT MOVE meaning I am stuck trying to impress him to spit out a buck- THAT REMINDS ME, today I had some MAN just stand in front of my case when I was playing and he just stood there.. still. I then started playing Immortality, my original song, and he finally opened his fist of loonies and toonies and fed my case like it was a starving Victorian child. I am not sure what he was contesting with me for, but I won apparently.

Right, so, I noticed that I can play 6 songs over and over for 1.5 hours and get great tips out of it–the only people sick of me would be the Cow’s co-workers. Another thing I noticed was that I was fortunate to have pretty equipment and have a performance look. What I mean by this is, I am distinctively unique in that I have short red dyed hair, statement earrings, an angst teenager style of clothing, my guitar is a beautiful 12-string Epiphone hummingbird, and my guitar case has a stunning red velvet interior. This makes me attractive and to hopefully combine that with my singing and playing style, I create a performance that is distinctly me, even if I am performing a cover.

Along the way, I realized that I was going to need a guitar pick. My nails have been in terrible shape for the past few months since getting acrylic nails removed (they were only for my guitar performance on the train, they’re like mini guitar picks, but they’ve been filed down to NOTHING). As of yesterday, I had come across a vintage MANSION (its name) and after exploring a THREE STORY HOUSE of vintage rooms and accessories, clothing, etc, I found guitar pick earrings for $5. This was a steal.. I bought them of course.

So today, I wore the earrings and conveniently took one out to play my set. I suck at playing with a pick but I like to think that every 58 year old man who passed by recognized my efforts and gave pity tips because they look at my guitar like they look at a 60s Nova… they don’t.

What are my hopes for my future in busking?

Since having multitudes of people staying around my guitar case for wayyy too long this morning, I’ve officially decided that I need more songs. I am definitely thinking easy songs that people know because nothing inclines someone to tip a busker more than hearing their favourite song — I usually try to appease to the older crowd with hits such as “Abilene,” “Love is a Rose,” and “Knockin’ On Heaven’s Door,” but I am thinking of playing some Taylor Swift now…Wish me luck.

I really do hope that I am able to grow my setlist to a higher duration without repeats, therefore, I will be able to attract more audiences to stay for longer. How else can I gain a crowd if they hear the same song they did yesterday and point and go “ew, ew, ew!!”

A plan I have also is taping my Amber Gray QR code paper onto the inside of my case. I keep forgetting to bring it with me when I go but I had that nice individual who worked at Harbor Hopper say that she can’t wait to hear my talent on the radio, like AWW. :’) (In other words, I need to better myself NOW with the setlist and other things if she has seen me ALL THREE TIMES.)

As a final note, I also want to mention that there are so many tips out there in blogs saying “BUSKING ADVICE!” and they say to buy this speaker, that amp, this guitar, that harmonica and do this, that, and you’ll receive this. What I am going to tell you is the truth: play like you mean it, use your body language to convey your passion and start young. Appease the crowd but don’t play songs you genuinely do not know, allow yourself to make mistakes, that’s unfortunately another way to get attention–and pity tips in my case. Be loud with your voice, be respectful if there’s children noise-sensitive or someone is obviously on a phone-call. The public is your stage, you are not entitled to being loud and in their faces because you want to make a few bucks. I don’t use a speaker, nor an amp. I just have my guitar, its case, a strap, a capo, guitar pick earrings, and a spirit combining an aspiring singer/songwriter and a college student in their first-year.

If you’re interested in busking, do it, do it carefully and know yourself better than those you perform to. You matter, always, and you are always enough — you won’t be perfect the first time. Now, I would tell you that mistakes don’t matter because you won’t see these people again but I have had TOO many people come up to me and talk to me about how they saw me this time or that or go to my school or are MY STAFF. (Oh yeah, be okay with people talking to you, it can either bring great wealth or great confusion that you’ll accept either way).

If you’re just interested in my yapping, then I appreciate it and would like to see your support :) Apparently Medium blogs have a clapping button so feel free to show your mere enjoyment through that or comment something–I’m not too sure, but I’d really appreciate it! Alright…

[Exit Gray]

(15:20)

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Gray Omeasoo
Gray Omeasoo

Written by Gray Omeasoo

Creative writer, authentic life-story teller, photographer, film-maker, journalist. Passionate about Mental Wellness.