27 Lessons that I have Learned in 27 Years

twenty seven lessons I have learned in twenty seven years of life as a writer, a hiker and a wedding photographer

I have a lot to learn, in life and in business. But as I have lived, and as I have gone through hard times and amazing times I have learned a lot. Some lessons are funny and amusing and some are heartwarming. Some lessons were tough to learn and some shaped me into a better person. These are not always about business and a career but I can vow that in one way or another each of these lessons has greatly impacted how I live my life and how I run my wedding photography business. I hope they encourage you, make you laugh, make you think and hopefully help you as well.

  1. Flat tires are temporary. This may be my favorite lesson, and it’s funny that I started with this. Cory realized that he was going to marry me during a weekend in the mountains where in two days we had two flat tires. The first one was manageable. We had made our way to Virginia Tech after setting up our tent in the mountains for the weekend. (I had an engagement session to photograph at Virginia Tech, then the rest of the weekend we were going to spend camping and hiking.) The second was not as manageable. We woke up to the flat tire in the middle of a desolate campground deep in the mountains, with no cell phone service. After a quick moment of silence, I searched my Jeep and found a “fix a flat” canister. Cory sprayed it and it put a little bit of air back into the tire. We spent the next two hours driving slowly through the rocky mountain road, that only took us thirty minutes the day before. We had plans to hike waterfalls that day but we realized a flat tire was going to put that on hold. After people turned down helping us, when we finally talked a resort into letting us use their landline to call Triple AAA (they refused to let us a few times) we waited for them to reach us for an hour. He filled our tire up just enough to get us to the closest tire store, only to be turned away. After searching we realized that the Walmart had an auto shop in the back and we brought our Jeep there. We spent the rest of the afternoon walking through shopping centers because we could not go into stores or restaurants because we had our dogs, while our Jeep waited in line at the busy Walmart. Eventually, the tires were replaced and it was the evening, we missed our chance to hike and exhausted from the day we drove the several hours home. We handled this together, problem solved and put our minds together every step of the way. We did that instead of getting aggravated with each other and butting heads. That was the weekend Cory realized that he was going to marry me and so for that I am thankful for those two flat tires! And because of those flat tires its one of our mottos to think of any hiccup in our lives as temporary flat tires. The pause button does not last, it does not become a stop button! They are temporary and if you keep working together it turns into quite a memory to look back on.
  2. Give more than you receive.
  3. Sometimes an Uber driver has the key to a happy marriage. Last spring, after a brunch for our newlywed friends, Cory and I called an Uber to take us back to our car at my Mom’s house and pick up our dogs! The Uber driver introduced himself, Roosevelt, and asked where we were coming from. I proudly told him, ‘my best friend’s wedding!’ Roosevelt replied, ‘so when is yours?’ We told him that it was only six weeks away and he replied seemingly overjoyed for us and went on to tell us that he has been married for thirty years! He had to be doing something right all of those years so I was inclined to ask, ‘so do you have the secret to a happy marriage?’ He laughed and smiled and said, ‘Well, all I can say is, I found the right girl. So find the right person and just stay married to them.’ Through it all, just stay married to the right person. I thought that this was pretty sound advice and even though it seems like a simple tip I am convinced that this man is very wise! The true meaning to his advice for us was layered with years of marriage behind him and I hope years of marriage ahead of him with his right person. Find the right person and stay married to them. Marriage will encompass the best of times, some hard times, wonderful times, scary times and what lies ahead that is completely unknown to us. If you are with your right person, well then all of those times will be together and you will never go a day feeling alone. I held Cory’s hand and thought to myself I found the right person that Roosevelt was talking about. asheville north carolina honeymoon wedding photographer balloons over asheville hot air balloon ride
  4. Our lives are more like a hot air balloon ride. We expand and contrast. We elevate to the point our heads are in the clouds and we also make a few descents along the way. But if we work with the wind, the ascent will always come again. We change directions depending on what winds are breezing by us. Did you know that the clouds that you are trying to reach so badly can be the very things that change your course? I learned all of that from our hot air balloon pilot. He knew more about winds and clouds and weather then most news meteorologists do! As for me? I teetered between feeling elated, with my head in the clouds, living on cloud nine and taking pictures to thinking ‘Oh!!! We are really high up’ and I gripped tightly on to the ropes as I stepped away from the edge of the basket that only went up to the lower part of my hip. When you think of the scary parts it can take away from the beauty and the moments along the way as your ascending to the clouds. I hope we all remember to put aside our fears as we adjust to changing winds. That way we can look around and see that we are already and currently living with our heads in the clouds! Like a hot air balloon you can make all the plans in the world, like which place in life you want to end up, where you want to be, or in this case which field the pilot wanted to land us in. But just like in life sometimes you have to adjust and make the ride work based on external factors. You will get there even if it is a different route or you might end up somewhere better altogether. Our pilot looked at the wind direction and made two attempts to land in an open field, unsuccessfully. This in turn gave us 45 extra minutes of our hot air balloon ride, and we ended up landing somewhere entirely different than he had planned. For us, we received a longer ride that was probably a once in a lifetime experience and the pilot adapted to the wind direction and changed his plans. Our bright multi-colored hot air balloon descended slowing into an older couple’s front yard and they came out to their front porch to watch and waved to us as we landed.  asheville north carolina honeymoon wedding photographer balloons over asheville hot air balloon ride
  5. Sundays are for adventures. Cory and I made a pact this past summer that Sundays would be for adventures together, because those were our only full day(s) together during the wedding season. I shared all about this lesson this past summer on my blog post The Sundays of Summer.
  6. Continue to show love to one another, no matter the tired eyes or the days you had been apart from separate schedules, because those are the moments you create that you will take with you for the rest of your lives. Find someone that you can lean against, that will hold you up and slow dance with you when you both can barely keep your eyes open. When you find them, never let them go. I photographed a wedding in Gloucester while my husband, Cory, was away for a couple of days being a best man at a wedding close to DC. After that wedding I drove three hours to meet him in DC. I just made it to see the bride and groom, our friends, congratulate them and get to our hotel room to upload all of my wedding’s images to my hard drive. To say I was exhausted at 2AM doing this, would be an understatement. To say Cory was exhausted would be the understatement of the entire year because I’m the night owl in our relationship! As I sat there and uploaded my memory cards, Cory started playing an Otis Redding song that he loves and asked me to dance. We danced, more like held each other up while we both leaned on each other to stay awake kind of dancing, but we danced in our hotel room.  I always love our lively dances in our kitchen while we cook dinner but I will always remember this dance filled with exhaustion and love.
  7. Remember to always show up. The people who sacrificed for me to chase my dreams, gave me the courage and push to build my business were my parents. On top of that, they just gave me the wedding of my dreams to my soulmate! We have been through tremendous grief and loss together, something a parent should never have to go through and somehow when it was perfectly acceptable for them to falter they still always showed up for me. I remember my Dad saying through pauses and his voice shaking, “we will not let this tear the three of us apart, because it is the three of us now,” and he held us, my mom and I! That was just days after our lives were forever altered, in the moments where we didn’t know if we were awake or if this was just a nightmare, he thought to say that and more importantly, he meant it. They were still my cheerleaders and I was their push to get out of bed in the morning. They had a daughter trying to get through college, grasping at an art degree and a dream to be a wedding photographer, amongst grieving. Even though I could not see it yet, I wholeheartedly believed that there was love and happiness in my future. Though, I knew that it was going to take a lot of work, grit and showing up to get there. That’s what my parents did also, they showed up. They sacrificed and then they showed up some more. I don’t know anything more beautiful than that and I will always try to find ways to show gratitude towards them and show up for them.
  8. Life is about ‘throwing candy’. I loved reading Present Over Perfect by Shauna Niequist and I want to share one of my favorite excerpts from the book and hope that it reaches anyone who may need it: “One of the traditions of this place is that when you see kayakers in the water paddling by from the nearby camp, no matter what, you stop and throw candy to them. Because it’s fun. Because it’s a sweet tradition. Because it makes people happy. If you knew me ten years ago, you’d say, that kind of thing is SO Shauna. But to be honest, I don’t know if you’d say that about me the last couple years. One afternoon, the kayakers crossed in front of the dock while a million other things were happening. Two large boats were docking, a sailboat, and a few paddle boarders were trying not to get in the way. All at the same time, in a small space. But the man who was in charge of it all, our host – the one who was responsible for everyone, stopped what he was doing and sprinted down the dock to get candy. I had a little panic attack, because what he was doing seemed irresponsible. He threw candy, in the middle of it. Over and over, handful after handful. And everything was fine. As I watched from the deck I put my head down and I began to sob. Because I use to throw candy, right in the middle of it all. I use to no matter what. Then I became the kind of person who threw candy as long as nothing else was going on, at approved times. And then I got so wrapped up in being responsible that it was never the right time to throw candy. Then, the worst thing: I became the kind of person who made fun of candy-throwers…What a loss – for me, my family, and laughter and silliness we missed out on because I was busy being busy. I’m done with that kind of responsible. I don’t want to get to the end of my life and look back and realize that the best thing about me was I was organized. I want to look back and remember all the times I threw candy, even when it didn’t make sense. Especially when it didn’t make sense. And that’s why I’m throwing candy every chance I get.” This, my friends, is what I want us to think about! I hope when I take women on hikes, play with my dogs, or go on trips with my Husband, I remember that it’s about ‘throwing candy’.
  9. Leave your mark on the world with your life, with your love story, your adventures, your work, your charity and within your friends and family. Give them something to marvel at by the way you make them feel, the way you affect the world around you and the positivity that you pour out.
  10. Drinking coffee is better spent having long conversations with a good friend in between sips.
  11. Roll with the punches. I finished college and got a degree because of this sentence. I was never an exquisite student. I loved the classes that I loved and I despised the classes that I despised. There was no in the middle and I was a student that was good at what I was interested in, only! But throughout college, I knew that I could not fail a class. I had to somehow make it work and I worked endlessly at the things that I was not ‘good’ at. My mentality was just to keep going, ‘failing’ was not an option and then I had to combine that with the last two years of college that I was grieving the abrupt loss of my brother. That was the biggest punch of all, and it was a punch I knew I had to fight back in order to graduate. It took time. It took rolling, dodging, detouring, and finally walking across a stage to receive that piece of paper. All the while having his baseball number on my cap, disguised as the year that I finally graduated ’13, and a note that I wrote to him that I taped to the inside of my cap. Roll with the punches. Dodge them. If they cause a detour, work at it and complete the detour, but never let the punches knock you all the way down.
  12. If you see something beautiful in someone, speak it. As a wedding photographer it is my desire to make every bride feel, scratch that, KNOW that she is beautiful! It’s in the way I photograph, the way I talk, the way I approach a portrait session or wedding day. It’s in the way I connect with my brides, befriend them and am always there for them. I want to take care of them! I see other wedding professionals and business owners writing about giving yourself grace, to embrace the perfectly imperfect. It is easy to see right to the heart of someone else’s beauty, someone else’s positives, but when it comes to yourself why does it become hard to offer yourself the same thing? Why is it so hard to offer yourself grace? I firmly believe that we are personally our own worst critic and knowing all of this we can still fall into our own trap. So I’m writing this for other brides, business owners and entrepreneurs even though, today, this is very much for me as well! asheville north carolina honeymoon wedding photographer balloons over asheville hot air balloon ride
  13. Spend time outside. Start where you are, take a walk or go for a run. Spend a morning at the beach or drive with me to the mountains. Wherever and however you can start spending more time outside, accomplish it. It has greatly affected my life and I am always noticing when I need more time in a week or even a day outside. It is good for the soul.
  14. Find someone to build the foundation of your life together. Like bricks built for a home; I believe that our lives consist of building layers of bricks on top of the foundation of our life. It begins and continues to grow with family. Layer by layer, brick by brick we build and grow the strength of our marriage, our family, our friendships and our lives. Find someone that will day in and day out build that with you. Alongside you. Together.
  15. Show love everyday. This is written in our home along with other commitments we like to keep as a reminder to us. It is extremely simple but full of meaning. Show love everyday in any capacity that you can. Say, “I love you,” do something nice for someone, spend time with someone you have not seen in awhile, listen to a friend talk about their life, hug each other. 1966 mustang wedding photographer virginia jessica ryan photography
  16. You’ll get a sign that they’re the oneTrust me on this one it will happen. It is different for everyone but besides the fact that I was already head over heels in love with Cory something happened on one of our hikes that gave the go ahead. The, “yep, you are marrying him. He’s the one for you,” was blatantly obvious and it all had to do with butterflies. The real ones that flutter around, even though I had them in my stomach too. You see, butterflies are a sign I have from my brother. You may be thinking, “how cliche,” but hear me out. My brother and I have a story surrounding butterflies that is one of my favorite memories of us as adults. It is one of the last happy memories I have with him. I have written about it before, but after he passed it seemed as if butterflies followed me, swarmed me, and landed on me. Fast forward to several years without Richard and lots of encounters with butterflies, my most favorite encounter happened. I was on my first hiking and camping trip with Cory, who I had only been dating for about eight months at the time. It was extremely hot out, to the point that later in the day on our hike up the mountain, we got caught in a thunderstorm and we were both relieved! Before that storm, we were hiking in a dense section of trees. The kind with no views and no real sight to the pay off just around the corner. Without any hint that the tree line would spread out and that we would enter a wildflower field, it happened. All of a sudden we were in chest high wildflowers. I was in awe with my eyes traveling, from flower to flower, I did not notice the butterflies until Cory mentioned them. When I finally did, they seemed to be traveling from flower to flower just as my eyes did moments before. Butterflies covered in brown and yellow colors fluttered all around us. Cory was behind me, so he could not see the one that landed on his hat when he turned. It was a large black and teal butterfly, the only one in the wildflower field. I told him and he froze and smiled at me. It would not leave his hat and I kept that moment to myself for a little while. I later told him that a black and teal colored butterfly identical to this one landed on my teal ’66 Mustang years ago while I was taking photos of it with my Dad. My brother was passed away then too and that butterfly hung out with us on the hood of my ’66 Mustang for close to an hour while we took pictures of our cars. Years later, in the mountains with a man I was in love with, my brother picked a black and teal butterfly to land on the top of his hat and hang out with us for a little while. Those particular colors when the entire field of wildflowers was covered in brown and yellow butterflies. It still gives me goosebumps as I type the words and relive it all over again. Richard was saying, “here he is, that’s the one.” I already knew this in my heart but it was beautiful to experience this.
  17. Arrive early to your commitments. I arrive early to everything and that is because I am terrified of being late! With wedding photography or portrait sessions, I like to see the venue I am photographing. I like to do a quick walk around and see what the light is doing and during that time I plan my “route” that I will take my couples on according to the light. I also do this on wedding day(s) in case of traffic. I plan extra time to get to a location. I want to greet the bride early if not right when I am scheduled to start photographing. I do not want to be outside parking my car or unloading it. I do not want to be saying hello to other vendors at that time as well, because to me that is showing up late for the bride and groom. I get there early so I can do all of that well before I head to see the bride and groom!
  18. “Shoulda, Woulda, Coulda, but… you didn’t DID!” “Shoulda, Woulda, Coulda, but… you didn’t,” his Jamaican voice spoke calmly but seriously. (I went to Costa Rica but our guide was Jamaican!) Then as a smile that reached from ear to ear on his face appeared, he gave an abrupt push on the rope and instantaneously sent my Aunt flying through the Costa Rican rainforest. My Aunt’s scream turned from frightened to overjoyed and I think I even heard laughter! That is where the saying that my aunt, my cousin and I say to each other was born! As my aunt’s feet dug into the wooden planks and she held onto tree branches, she was saying that she should have stayed down at the main building, that she would have stayed if she knew it was this high up, and asked if she could turn around and walk down. This Jamaican man created a saying out of thin air that we will take with us for the rest of our lives. “Shoulda, woulda, coulda, but… you didn’t,” and after she DID in fact do it, all of it, we changed it to, “Shoulda, woulda, coulda, and… I DID!” As I flew through the rainforest I kept my eyes open, I looked around at the Tucans, the animals that I could hear but could not see and the ocean in the distance. When they asked if we wanted to zip line upside down I listened carefully on how to do it! As the wind began to fly through my hair I gripped the rope tightly, swinging my legs up, just under the zip line itself, and pushed my shoulders and head towards the ground. I was upside down flying through a rainforest in the mountains, and though I was going to fast to recognize any objects while upside down I had never felt more free and alive. For adventures, experiences, dreams and goals one of my mottos was born that day, “shoulda, woulda coulda…. did!” girls who hike sharp top mountain peaks of otter blue ridge mountains
  19. Try to do something meaningful on hard days. For over a year I have wanted to begin to build a community that uplifts each other. A community that hikes beside each other and will be there to listen to one another. To laugh, to encourage, to empower; I wanted all of these things for the women who would come to hike alongside me. I share the reasons why I love to hike and what it gives to me in return. Now, it is my mission to give all that I have gained from it, away. Because I believe your joy, heart and passion can only be multiplied when you decide to give it back to others. I know first hand what hiking mountains can do for one’s soul. I know this because my brother, without knowing it, instilled this within me. I hike because of him and I am at this place in my life partially because of him. Unfortunately, I learned these things after he was gone, but it has made me see our world with a different set of eyes. And in that world I cherish the ordinary, the small moments and the smiles of others. I have set out to bring others joy and on my brother’s birthday, I took five other women on a hike in the mountains, to some of their very first mountain peaks. What happened at the top of this mountain when I shared that it was his birthday with them is something I will always remember. A community was formed. I think we all have our own reasons for lacing up our boots and setting out to accomplish something, but that’s what made this day so beautiful. It was everyone’s individual reasons for coming on this hike and that we all did it together. One woman said, “Thank you for sharing his birthday with us, Happy Birthday to Richard.” Women who were strangers to my brother, were at the top of a mountain with me and said happy birthday to him in their own way. In that moment I realized that my life was exactly where it was suppose to be. That this life was meant for giving to others and that I was on the right trail of doing what I was destined to do. I think Richard would have been proud to spend his birthday the way we did.
  20. The green stuff at a sushi restaurant is NOT a small serving of guacamole. Yes, this happened to me when I was in middle school and at my first sushi restaurant experience. If you want to avoid running to the bathroom and sticking your mouth under the sink faucet (that sounds so gross to me now being that it was a public restroom). If you want to avoid feeling like your esophagus is deteriorating in an instant, heed my warning! I love wasabi now, but it took awhile! Don’t rid yourself of joy from sushi because of the guacamole/wasabi confusion. wedding photography living a legacy personal
  21. Take pictures! The importance of photography and cherishing these 4x6s that I flipped through with my fingertips is a thought I can remember always having. I am not sure when it began, but I know as a little girl I would take all of our family photographs and hold them hostage in my bedroom. At a young age, I just did not want to lose them. Roughly five years ago, when we lost my brother, we also “lost” four photo albums. This included baby albums, a family album and my parents’ Wedding album. Now losing these photographs did not compare to the magnitude of what we really lost that year, but the timing was downright awful. We turn to photographs in moments like that and besides the box of photographs that I kept within arm’s reach all of those years as a child, the others were nowhere to be found. As my parents unpacked the attic one evening together a few months ago, they found not one but all four of these photography albums. I received a message from my Mom that evening, “I found our Wedding album, and other ones too. I thought to myself, asking Richard to let me find them today.” I find it fascinating that when my Mom was ready, she asked and within the same day they found them. I went over to my parents’ home and looked through everyone of the albums. The photo above is of my Mom and my Grandma on my parents’ wedding day! Before I was even a thought, a photographer came along on my parents’ Wedding Day and gave me moments like this to always cherish. I hope this is a reminder for everyone to take photographs, take TOO MANY photographs! After that, print them, save them on external hard drives. Showcase your photographs in a tangible form whether that’s on the walls of your home, in photography albums, or even on your Instagram. Capture memories in time so that little girl, that saves them all in a shoebox because she wants to keep them close, has photographs that teach her the importance of photography.
  22. Be fearless in the pursuit of what sets your soul on fire.
  23. If you don’t see the group that you are searching for, create it. Her Hike Collective has been that group for me! You can read all about the hiking group I created and why I created it on all of my blog posts about it here: Her Hike Collective Blog Category
  24. Celebrate the dog’s birthday! Because it is fun and hilarious and childish! Sometimes it turns out to be some of our funnest weekends together. We love our dogs, it’s true, but any excuse to go hiking or camping or for ice cream or to the beach, you know for the dogs are all great reasons to celebrate the dog’s birthday.
  25. Laugh often.
  26. “Find the grace. Find it & hold it & cling to it like it is your lifeline. Find the silver linings. Hold them in your lungs & search for them in the bubbles & rubble of all that pours down around you. Find the bright spot in the dark clouds, listen for the sound of birds when the winds pick up. It is there, it is always there & it is waiting for you to reach out with both hands & hold tight to it like it is the last thing you will ever learn how to let go. Find the glory & understand that it is what we can endure that defines who we become. Rise & find the grace, for it is all around you.” -Tyler Knott Gregson
  27. Make your mess your message – Ishita Gupta. Jeff Goins hosts a writer’s conference called Tribe Conference and I saw this quote from his blog post about his takeaways from the conference. Goins writes, “Don’t try to hide the unkempt parts of yourself. Let your hair down, tell the ugly parts of your story, and allow people to love you for who you really are. With Tribe Conference, this means acknowledging when things don’t go well. We are intentionally not going for ‘polished.’ After the event, I would publicly share what we did right and what we cold do better. My friend Bryan Harris calls this ‘learning out loud.’ This means that as you create the thing, you talk about what you’re doing right, what you’re doing wrong, and what you’re learning. This is not a license to be unprofessional, but when you share how raw something is with your audience, if you don’t try to hide your mess, people don’t criticize you. They cheer for you.”

These are my 27 lessons that I have learned throughout my life and if you got through them all I hope that they helped you, encouraged you and made you laugh a little too. Some have a long description and some are short and sweet. Our best lessons have stories with grit and I have been writing this blog post all year to get it ready. I did not want it to be perfect but I wanted it to be well thought out. I wanted these 27 lessons about life to be meaningful and hopefully impactful to others. Hold onto your grit, don’t give it away but share it if you feel inclined. Make your mess your message.



Jessica Ryan