Challenges in Event Planning: One Woman's Guide to Success | Dera Lee

Are you a woman who is looking to rise to the top of the event planning industry? Are you an industry newcomer who is struggling to adapt to the chaotic life of an event planner? Whether you are brand new to event planning or a seasoned pro, it is helpful to master strategies that can help you cope with the challenges and unpredictability that accompany event planning. 

In today's episode, we'll cover:

  • The top challenges in event planning that can overwhelm new producers
  • The #1 key to success for women in the event planning industry
  • The formula for landing big brands... even if your business is in its infancy

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The top challenges in event planning that new event producers may face

Today I talked with Dera Lee, Founder of Dera Lee Productions. With a background in theater, Dera Lee approaches event planning through the lens of a storyteller, as if the event were a high profile Broadway show. Dera shares the keys to her success as the founder of a female-owned production agency in New York. 

Dera notes that the path to prosperity for event planners is often a rocky one - especially during the planner's early years. Women entering the industry are often caught off guard by the long working hours, office politics, and high levels of stress that they face on a daily basis. And the recent impact of COVID-19 shows how unpredictable events and crises can present major barriers that require innovative strategies to overcome. 

The #1 key to success for women in the event planning industry

Coping with the daily challenges of event planning is not for the faint of heart. As if the obstacles above were not enough to contend with, some women find themselves grappling with "Imposter Syndrome." Rather than moving forward with confidence in their careers, they are overcome by negative thoughts and feelings of self-doubt.

The single most important key to overcoming these obstacles is PREPARATION. Women often enter the field without a strong working knowledge of what a typical day in the life of an event planner is like. They often underestimate the long number of hours event planners work, and are not armed with coping strategies to help them deal with daily stressors. But through preparation, these roadblocks can be broken down.

A woman at a computer with her hands on her head because she is facing challenges in event planning

If you are considering a career in event planning, there are several effective ways to prepare yourself for what lies ahead. First, you can volunteer or complete an internship at an event planning organization. Second, you can find a mentor with a proven track record of success in event planning. And third, you can ask a friend or colleague in the industry if you can shadow them for a week or two. All three of these strategies will give you a taste of life as an event planner. 

The formula for landing big brands even if your business is in its infancy

In addition to being adequately prepared to face event planning challenges, there are three other measures that will help you land your dream events, even if your business is in its infancy. Dera references three important strategies that will help you achieve your career goals:

  • Always maintain a focus on building and maintaining your business relationships
  • Establish a daily routine and do your best to stick to it - even in the face of adversity
  • Never lose sight of WHY you became an event planner in the first place

By maintaining your focus in these areas, you can achieve a healthier work-life balance and remain passionate about your livelihood. More importantly, your focus and balanced approach will keep existing customers happy and help you land that big brand you have been eyeing.

 There are so many challenges in event planning and the event production industry @deralee shares here secrets to a successful business and personal life #events #eventleader #onlysuccessfulevents #events #eventplanner

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Would you like to unlock your potential as an event planner?

As outlined above, you hold the key to your success as an event planner. One of the best ways to expand your industry scope is to Get Listed by submitting your business to the Only Successful Events Directory. By taking this important step, you will boost your authenticity and reputation as an event planner while helping new clients discover the value you can bring to their organization. 

Full transcript of interview on the key to overcoming event planning challenges: Women's guide to success

AI: (00:02)

Welcome back to the only successful event show. I'm your host, April Iannazzone. Today I'm joined by another tremendous female business leader, Dera Lee from Dera Lee productions. The topic of today is the key to overcoming challenges in event planning. So Dera, before we jump in, can you tell us a little bit about your background?

DL: (00:25)

I'm happy to. So I actually began on the Broadway, on a Broadway stage. I went to NYU school of the arts and I started performing across the country. That's where I discovered that the magic was behind the scenes. My passion for planning and storytelling led me to planning for some of the top agencies in New York City. 

I eventually opened my own agency in 2015 working for some of my favorite brands, such as I'm creating events for new brands such as Adidas, Brooks Running, Cover Girl and one of my favorites Secret Deodorant. In 2019 we actually helped promote the U.S women's soccer team, at the world cup in Paris, France this past year.

AI: (01:16)

That's incredible! it's incredible how all different backgrounds really fit into not only the event world but also the agency world and how you pull from all different resources. 

DL: (01:30)

 I wanted to create events that weren't formulaic. For me, because of my theater background, I really wanted to create dramatic events. To tear down that fourth wall as you call it in the theater world because I really wanted the opportunity to help create an ad that you could step into. 

I think that some of that is missing from events. A little bit of the storytelling sometimes gets lost. In the fact that my background actually is in theater, I'm a natural storyteller, so I always want to make sure that story is told. So for me, theater I believe to be transformative and I think that events can too. It’s really why I started my agency. Honestly.

AI: (02:08)

I love that and I totally agree with you. A lot of times it's more of how can we get an event and have it serve its purpose. Rather than what is the experience, the feeling, the emotion and the story that goes into the event. Do you have any examples that you could share of how you bring storytelling into an event?

DL: (02:27)

I think one of the examples that come to mind right off the bat, was our event through Lufthansa.

 It was their 60th anniversary and we wanted to recreate a 1950s airline terminal, based off the brand Lufthansa. We overtook a park in New York City and recreated in the park a 1950s terminal. The whole story was told not just through nice pictures and through props and setting. We brought in airline stewardesses from the brands today, brought in a brand ambassadors and actors to play the parts of passengers. 

The people that were leading in the event were talking to real-life passengers at the time, giving them scripts to interact with guests. I think that for me it was really about interacting with customers and having them live the life of a passenger in that time period. Bringing theater flare to everything. It's always a fun way, a memorable way for people to take that event with them. That's just the way we like to do things here.

AI: (03:56)

I absolutely love that. I'm sure you got some amazing pictures from that event as well. I could just picture everybody dressed up. That's very cool. And I'm sure that's also an event that your guests were talking about to everybody and really sharing that experience.

AI: (04:14)

Before we jump into how you grew this business so fast and how you think other women can really own their place in the industry, I'm curious how you landed some of those first big brands at the beginning? Whats the key to overcoming challenges in event planning?

DL: (04:29)

For me I was really lucky and I hate saying that because it's also hard work. Before I started my agency, I worked for many other top agencies in New York City and had definitely built relationships. I built relationships with all those clients I had and really done my homework. For me, it was building that network and keeping people close with that network from former agencies. 

When I was ready to open, I obviously was prepared and ready to present them with our capabilities, with projects that I had done before. Giving that first opportunity for them to bid was a real special occasion for us. I think giving them special treatment obviously and making sure that we would give them a little bit of a discount as a first client. 

For it was really about building all those relationships and keeping those relationships when I was first starting. That is what really gave us our big breaks at the very beginning honestly. And keeping our clients is always about doing the hard work, making sure that the event is a success and making them happy.

AI: (05:54)

I love that you leveraged your past relationships too. So even if it was a project that you were working on in your previous agency, you've never burned the bridge. You kept the relationship open completely, not only with the projects you were working on but hopefully with the other agency as well.

DL: (06:11)

Yes.  It's a small experiential marketing world so we all root for each other. So it is so much easier to overcome challenges in event planning. We all understand that there are enough events in the world to keep us all going. And understand that there's always going to be competition, but it's always healthy.

AI: (06:28)

I love that. I really did want to have you on today so we can discuss developing the next generation of female leaders. My whole mission in business, not necessarily this Only Successful Events brand, but my other brands, is really to show every woman. Well everybody out there, but particularly every woman, more specifically my two daughters, that they can generate any amount of money at any given time if they are willing to put in the work and do the right things. 

It's a limitless opportunity. And I feel like it's a message that a lot of times there are extra hoops that as a woman you have to jump through. But a lot of times as women I see people using different situations as a crutch almost, or an excuse not to really move forward. I know a lot of people say, Oh, I have kids at home. I can't do this. If it's something you want, there's always a way to figure out how to do it.

AI: (07:35)

So Dera, can you tell us what you think it means to develop that next stage, the next generation of women for the events industry?

DL: (07:46)

It's really getting them prepared. Honestly, I've been lucky enough, to work for many agencies. When I was working at those agencies, I would always get approached by a lot of the younger women that were working at those agencies for advice on everything from office politics to negotiating their salaries. 

I've had my agency for almost five years now and even the women that I'm interviewing now, five years later since I've left other agencies still don't seem prepared. For some reason, it's not growing and knowledge isn't getting out there. I really want to be able to mentor, help or teach in a way that helps them understand what they're getting into at an event agency. What the office politics are like. Obviously this can happen at any office, but in the events world, it is a different pace. It's a different life.

DL: (08:54)

The key to overcoming challenges in event planning is by understanding what they're going to get into. How to negotiate, how to be prepared and be successful, and how to stay the course in this highly stressful industry. it's highly competitive. There are now colleges that are actually offering degrees experiential marketing, especially in the design world and production.

There's really no course to be had besides online things out there. I want to make sure that they are well prepared. I think the knowledge that myself and some other women who are in that senior role in a sense, that have been in the business for maybe 10 plus years. So you really have that knowledge and can help that next generation to be better prepared and lead into that next generation.

AI: (09:51)

The internet makes it more of an environment where it looks like it's so fun and so easy to get into and so easy to break into the next level. A lot of times it's about having thick skin and being able to get up the next day, go and do the same thing in a little bit more strategic way. Can you share some of the things that you wish you would've known when you were first starting out?

DL: (10:23)

When I first started out as an event producer, when I was in my early twenties?

AI: (10:32)

Yeah. Let's talk about way back when you're fresh out of school. When you decided to leave the theater world. What challenges in event planning and building your business did you face?

DL: (10:39)

I will say I was lucky in a sense. The theater world did prepare me for long hours. Understanding how to work nights and understanding to get up the next morning was not a chore it was a pleasure. I think the biggest thing that I would tell people to be prepared for is the long hours. Well, there’s a couple of things I would tell them, I would tell them first you need to understand your why. You need to understand why you're doing this every day. A reminder in the mornings to tell yourself why you're doing this every day. I think that's really important. 

I'm also a very big meditator. We live in a world that can be very stressful. It's very up and down. Learning how to center yourself and learn how to breathe for most moments is really important to me. I would tell any producer or any designer in this world to do that. Making sure you take care of yourself, exercise all the time, eat well.  Drink water like it's going out of style. I don't care if it's you put a flavor in it just drink it.

AI: (11:48)

I am a hyper hydrator guys. My 40 ounces sit right in front of me so I totally agree with you!

DL: (11:54)

An event producer is up there in the top five most stressful jobs literally in any industry. It's there for a reason. You are working day and night for an event that could potentially happen in one day. We're producing events that are 500,000 million dollar jobs that are for one day. And that's a lot of stress to put on a lot of people.

Finding that mindset of why you do it and making sure that you enjoy the journey. I think that it can be hard in those stressful times when everyone's worried. And especially now, obviously, we've got some things going on in the world of the coronavirus. All of us all in the industry are really trying to be optimistic and understand that things will pass. But keeping that level-headedness is really, really important to any producer.

AI: (12:45)

We had a guest three shows ago, she had a multimillion-dollar event cancel days before the event. It was supposed to happen last weekend in Los Angeles. So definitely coronavirus adds to the already stressful position.

I am really curious when you first got into the agency world, not owning your own, but when you started.  What were some of the things that you wish you would've known, as far as office politics or working up that ladder?

DL: (13:24)

Well, I am a very big self-starter, so I was always really interested obviously in event producing, I'm an event designer, so I always loved numbers. I was always a budget person, I always loved it. It made me understand that when I went into negotiating or whenever I was working on understanding what salary or what I would worth. I really had to figure out what I was worth in the sense of what was I working on? How do I bring work to accompany, what kind of value am I? 

For me, I learned really quickly that I didn't know when I first went in was how much I was worth and how much my value really meant to that company. How do I put that to a salary that makes sense? A lot of women in this industry first start and they just take what they can get. We want to make sure that the bar is set a little bit higher. 

So when the next generation comes along, it's not so hard to move up. A lot of us are not hourly workers except for maybe some freelancers. But I think that in general, making sure that you understand how many hours you working based off your salary and thinking about all those things.

AI: (14:47)

Because sometimes the salary sounds really great, right? And then by the time you work out how many hours you just worked on a project it could be crazy.  Definitely one of the biggest challenges in event planning industry!

DL: (14:59)

It could be crazy. I know that it comes a little bit with the course, I understand that. The world of events, everything's really about community. Literally you are depending on every person. There's no man for themselves. As any producer says, you are as good as people that you're working with as well as your vendors. 

It's a part of the course you're going to work a little bit longer than most. But understand that when you completed a job and when you are successful that you understand what value that brings. From a numerical value to the relationships that you bring. That you really take notice of all that.

DL: (15:39)

That's just something I didn't understand. I probably learned that my first two years coming in when I put numbers to paper. Cause I am a numbers person. I think that was a lesson learned.

Really it's now something that a lot of people talk about when negotiating. But it's still surprisingly something that I hear a lot of women, in the industry that don't know how to put that to paper when they go into maybe a review.

AI: (16:09)

I absolutely agree with you. I'm going to turn it a little bit here because we were talking about when you were working for other people. Now you work for yourself and you are the owner. I want to talk about something that happens a little bit with men, but more so with women and that's the imposter syndrome. That's, do I really deserve to have this big account? Am I going to be able to pull this off? I can't believe they picked me. All of those things that are going to go through your head until the event is actually over.

Did you have any of that when you first started? I'll tell you every level that I get in business that always comes up and always creeps in no matter what level I'm going after. So I don't want everybody listening to think that it's this one thing you're going to have to overcome. But I want to hear about when you first decided that you were going to own your own agency and how did you have that imposter syndrome? What is the key to overcoming challenges in event planning?

DL: (17:10)

I definitely did when I first started. 

DL: (17:18)

 Not so much that I didn't deserve it cause I knew that the value, the work, and the creativity that we would supply our clients would be amazing. I never felt that but I always was just like, Oh my gosh, this is coming to me. And I think that it was a balance of just accepting it. 

When I go back to my value of when I was a  20-year-old thinking about my value to a company. It's really the same mindset of when I started my company now, it was like, okay, well I am creating value for my clients.

DL: (18:06)

I am bringing them a high level of success where the impressions are through the roof. The audience attendance is more than they expected. I think I definitely experienced it, but again, I go back to the mindset thing.  Every day I remind myself why I'm doing this. Why clients returned to us. 

Why I love what I'm doing and why we do successful events. Honestly. Because I think that many females experience this and I think that it can always creep in. I'm never going to say it doesn't ever creep in. It definitely creeps in once in a while.

AI: (18:56)

It doesn't stay there.

DL: (18:58)

 I don't allow it to cripple me, if that makes sense? like anything in meditation, things are always going to creep in. Worry, doubt or imposter syndrome. It's about acknowledging, saying, okay, I'm feeling this, but reminding myself that we've done all of these amazing things already and the fact that we can do them again, we'll do them again. Because that's what keeps us going and keeps me going every day and really why I keep going back to that everyday mindset.

AI: (19:32)

I love that. As I mentioned, whatever stage in business I moved to or if it's a new venture, it is something that always creeps in. But It's how quickly can you correct that thought process. Or feed in, as you said, we've delivered this before. We are going to deliver it again and just almost, not talking yourself out of those negative thoughts, but reframing what you were even thinking. 

DL: (20:01)

There's a couple of books I always recommend to read. Jensen shero you're a badass is probably one of the reads that I recommend to every female out there. She's one of the best, with kind of my sensibility. The book has a lot of humor and she's kind of that a little bit of jaded New Yorkers. 

I love her, her sensitive humor to it, to self-help is great. And she talks about in the imposter syndrome in there a lot and how to reframe it.  Because everyone really has it, it's just something that needs to just be tweaked.

AI: (20:47)


AI: (20:48)

Now you keep talking about your why, and I love that because to me I have my why right at my desk that I look at every day. I journal in the morning and we'll be talking about your morning routines in a minute. But what is your why? What really keeps you going?

DL: (21:09)

From a business standpoint or from a personal standard?

AI: (21:13)

I guess a little bit of both if you don't mind sharing? For me they're actually both one and the same.

DL: (21:20)

My why is a little bit different for both. For my personal is for my family. I'm recently engaged and bought a home. I think that for me it's about family and inclusion. Wanting to build a life for my family and friends. That's what keeps me going every day, and thriving me every day.  My professional why is really for my clients honestly.  I'm all about the process, and always wanting the process to be as enjoyable as possible.

 I've worked for many agencies before and I really want to make sure that the process is as smooth and as easy and as enjoyable as possible for my clients and really making their life easier. 

We do such great work that I really always want my clients to have just an easier, better life and make sure that what we bring to their lives is bringing success to them. I know that that's really what it's all about. Our events say something, but also the relationships that we have with our clients are really important to me and important to everyone at my work. I want make sure that those relationships are really great.

AI: (22:59)

I love that you shared your family is your why. Now I work with a lot of women entrepreneurs with my self-made success brand and a lot of them are always a little ashamed to say that . They really want to think about the bigger vision and just want to help people and give back and all of that, which is great! We want to do that. that's part of my bigger piece but first and foremost is, am I providing for my family? Whatever my family goals are, that's my why. That's why I get up every morning and pushed myself so hard.  Why I do everything that I do and how it goes into why I say it's one and the same with when it's business or not.

I really do want to set an example for my two daughters as well as other people of what is possible and there's a whole other big thing behind it, but it goes hand in hand. And I love the fact that you are being real too. And we both want to help people. Your goal is to mentor other women in the space and really help them as well. But you can't do that if things are not the way that you want them at home. You have to take care of your home base first.

DL: (24:23)

I think it goes more hand in hand. My family is foremost the most important thing to me. Could I mentor women without having a company? Yes. I do feel though that I want to set an example. To make sure that you show them that whatever you set your mind to you can do.  I'm the oldest of six siblings so I literally lead by example. That's all I know how to do. I can tell them a million times I do something, but they'll, they'll listen to me and everything goes out the window

AI: (25:02)

So you're going to have a really big wedding party, right? With your six siblings.

DL: (25:06)

It's going to be humongous. That's a problem. I've learned that having six siblings who are all millennials, they learn by example. I show them that I show up every day and we work our tail off. They see the hours that I put in, they see the drive that I have, and what I want to accomplish in my life and the goals that I have for my life and my family's life and my company. 

So I think that in the end, that's what leads to hopefully guiding younger women and being able to actually not just tell them what I do but actually show them.

AI: (25:47)

Perfect. I love that. Now, most successful entrepreneurs have a daily routine and, something that they're pretty regimented or ritualized. Do you have one that you could share?

DL: (26:00)

I think it goes a little bit back to what we were talking about before, literally my morning routine is as follows. The time varies, I'll be honest, depending on what event happened the night before, but I will say my morning routine is getting up. I meditate every day for 10 minutes with the calm app. From there I do energy kinds of breathing exercises. Then get up and exercise for 30 minutes, either yoga or running, I’m a big runner as well. After that, I do business and personal affirmations. 

It's me reaffirming the reasons why I'm doing what I do every day for me personally and reaffirming all of my business affirmations for me every day. Meaning why the business is running, what's important and what our values are. It sets my brain and my mind in the right path of when we're talking to our clients I'm running in and not letting me sweat the small stuff that happens in the event world every day. Then after that, obviously I shower and change and probably walk my dog and feed my dog. Then off to work I go.

AI: (27:24)

Do you say the affirmations out loud or is it something that you're writing down or are you just thinking through them?

DL: (27:33)

I'm a big talker. Sometimes if I'm rushing and I still want to get them out, I might read them to myself in the subway. If I’m in my home I do say them out loud. I think that it's a big deal to hear them, actually saying things out loud all the time. I have vision boards. Everything I do is about making everything that comes out of my mouth and in my mind come through. That's the only way that works for me.

AI: (28:10)

I'm the same exact way to me. I want to say it, but I also want to experience the feelings. So I'll do affirmations and I'll write them and I'll say it, but I'll also write down what I want outcomes to be. If we are going after a big deal or something like that, then I will write down what I want, how much money I'll see in the bank, and then I will try to really feel it.  Sometimes I look ridiculous. I hope no one's watching, you know, I go through the whole thing. 

I don't teach on mindset at all. I'm all about strategy and here's what I need to do to make it work. But I believe in mindset. 100% that it is something that needs to be worked on every day and little pieces need to be sprinkled and implemented throughout your day to really have that overall outcome that you desire in both life and business. With the event world in first you have to find the right spouse that understands the event world. So is he in that event industry as well?

DL: (29:20)

He is amazing and is also in the industry. We met when I first became an event freelancer. He was working in the fabrication industry. I’m very lucky that he understands the hours that I've put in and just the events world. It’s not linear, nothing's linear. So I'm very lucky to have someone that's been in the industry and understands that.

AI: (29:51)

Very, very true. Some people say you walk to into your home doors and you leave your work life behind. I never could really do that, but do you have any ways of dealing with not letting them cross over? I hate saying work-life balance, but not to let it interfere with your home life too much.

DL: (30:12)

It is hard. I'm not going to say it's not. I think especially for someone who obviously understands the same industry. You want to confide in someone that obviously understands the industry that you're in. My advice coming from experience is when I come home and I don't want to mix oil and water it's really about settling the mind

The only way I tend to end up doing that is I take a moment and I go back to my list of gratefulness that I have in my life. When you're so stressed out and kind of forget what you have in your life. I don't know why that happens, but you're just caught up in all the small stuff.

DL: (31:15)

Why someone didn't call me what happened, what vendor did this or whatever it is. And you forget what's really, really important sometimes. Then you're short with your loved one at home because you've had a hard day. And that's obviously not fair to them or, or to you. So really taking a moment in between your work and before you come home and taking a moment to be grateful for those people that are in your life. That's the key to overcoming challenges in event planning.

Grateful that you can come home to that man or woman in your life that's cooking you dinner because you've had a long day or already has that takeout spread out on the kitchen table for you or has poured that drink for you and understands that you're stressed. That’s something I do a lot of to really separate and let go of the workday.

DL: (32:00)

Again, I always go back to things like if you have that time to meditate, going out for that run before I get home to just separate that time and let things go. The grateful moments for me are really the ones that were the most impactful because I come home and instead of being a little bit grumpy sometimes if the day kind of hit me hard.

 I can come home and smile and look at my fiance go on I'm really happy to come home to you. Not go right into all the things that went wrong today. He's really great too. He reminds me to do that a lot as well. I'm very lucky to have a partner like that.

AI: (32:47)

Thank you for all the little golden nuggets that you shared throughout. So where can people find you and we'll put everything in the show notes, but why don't you tell them to.

DL: (32:58)

You can definitely reach out to our website We're always hiring. So if you'd like to reach out to me directly, that's completely fine. You can email me at Just let me know in the subject line where you found me, obviously April’s show. Going to my website's a great way to learn more about us.

AI: (33:29)

Thank you again and I hope to have you on in the future because I know that you have much more information that our audience can benefit from.

DL: (33:38)

Lastly, thank you so much April for allowing me to share how I move past the challenges in event planning I faced. I hope sharing my experiences will help the views! Have a good rest of your day.

Guest Expert on The Key to Overcoming Challenges in Event Planning 

 - Learn more about Dera Lee and Dera Lee Productions 

Dera Lee is the founder & CEO of Dera Lee Productions, an award winning event design and planning agency in Brooklyn, NY, that approaches every event like a Broadway show by producing detailed, technically precise events that can transport the audience and even be a little magical.  After attending NYU's Tisch School of the Arts, she performed on many stages across the country and discovered that the magic was actually behind the scenes.

Her passion for planning and storytelling led her to work with many top event planning companies in NYC, eventually opening her own firm in 2015 creating events for some of her favorite brands such as Adidas, Brooks Running, Covergirl, and in 2019, Secret Deodorant, promoting the US Women's Soccer team at the World Cup in Paris, France. 

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Dera Lee
Founder and CEO of Dera Lee Productions

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