Venting: Overcoming Challenging Obstacles

I love receiving all of your questions on Mondays. In a way, they also help me keep in touch with my own stuff and remind me not only to “talk the talk” but “walk the walk.”

I hope I responded to all your questions last week (if not, let me know). Among the many questions, dear Norah wanted to know about the most challenging obstacle I have faced in life and how I overcame it.

Looking back at my business life, the most challenging obstacle I overcame was 15 years ago: I almost went out of business.

Even though I was creating work that was considered different and unique (thank God), because of poor management and my lack of interest in the business side of my company, I owed a million and a half dollars to my vendors and taxes. It took me over 5 years to solve this major problem.

I remember this as being a very scary time of my life. I remember hiding from my vendors when they called for payment and being afraid of being arrested for not paying hundreds of thousands of dollars in back taxes.

I spent many sleepless nights beating myself up, asking how I could possibly let this happen?

Of course there are daily challenges for anyone running their own business, but even today there is nothing that comes close to how scary that part of my life was. I’d like to go into greater detail tomorrow and Thursday about how I went from this overwhelming challenge to running a profitable business.

In the meantime, it occurred to me that I am pouring my heart out to you without knowing more about you than your name. In this week’s venting, it’s your turn. Please tell me about yourselves. For instance:

  • What area is your business in?
  • How long have you been in business?
  • What is the most challenging business obstacle you overcame?

And, of course, if you are currently experiencing any business challenges where I can help, please leave your question in the comments and I’d love to answer you directly by email.

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  • Aleah + Nick Valley

    What an open and honest post. Thank you for sharing! We are going into our eighth year of wedding and event planning and our biggest struggle is separating work life from home life. As we both run our business together, we often find ourselves talking about business non-stop. We absolutely love what we do and are so grateful to being involved in couples’ special celebrations, but finding home and work balance can at times be challenging. How do you separate work life from home life?

  • Trendee Flowers

    Thank you for being real . This gives me the motivation in by Buisness . Being inspired not only by your words of encouragement but by your creative creations that you share with all of us. Greatly appreciated !

  • Frustrated and Greatful at the same time

    I am literally crying…tears pouring down my face as I type this. God had to have known I needed this today. As soon as I opened my twitter page, your message was there….. I am a custom invitation designer that is at a crossroad with my business. I basically have the same challenges you had years ago..but not the exact dollar amount. I am very creative and is at a point in my career that I am in demand….But cannot seem to move my business from this place…..I cannot seem to get the business side together. I cannot find the right people to help because I do not have the money to pay them what they deserve…I have been designing invitations for 8 years. I opened my studio three years ago. I love nothing more than designing invitations outside of my family. I have no other option but to do this. God showed me when I was 8 years old that I would be in a creative field…….I had no idea how hard the business side of this would be. When you are running a business by yourself, you feel that no one else understands the everyday challenges you go through. Although I cry about my troubles, I have never thought of giving up. If I gave up what else would I do. I know I belong in this field because when I create a custom invitation for a client the reaction I get from them is priceless….I know that I am different, Great and destined to be the best! I attended a seminar that Sean Low gave in Atlanta last year and he spoke about your business….His words were very encouraging. I left that day and cried my heart out and prayed that some how I will succeed not only in the creative side but the business side as well. Any advice you offer will greatly be appreciated. Thanks

  • Corrine O’Neill @ Buds and Blooms

    This, and stories like it make me feel like I can succeed. I know of tech entrepreneurs who also faced the same challenges; now money is not a problem. My biggest challenge is having the confidence to believe that I can succeed; that and getting found without having a large advertising budget. I make handmade fabric flower bridal accessories and my shop is less than 6 months old. How do I set myself apart from the competition; especially when there are already clear leaders in my segment of the industry?

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  • Wendy

    I am a planner in Philadelphia, Pa. I have been in business for 7 years. My business was growing until 2 years ago. Now, I am on the verge of losing my house, I can’t pay my bills and the leads have dried up. I NEED this business- it is my only livlihood and I have two little grandchildren who are financially, physically and emotionally dependent on me. I love what I do and I am good at it. I have tried everything! I don’t know how to get the message out there about what I do and how. I have a blog- that I have neglected terribly lately. But, even when I posted every day- the leads don’t come. What can I do?!


    Thank you for posting articles like this one. It is my belief that most of us in the event industry have a creative calling and yet we do not pay enough attention to the business side until it’s out of control. I am in the middle of my scariest time at the moment. The clients are lined up but I haven’t charged them enough to cover all of the mounting costs of running an event flower business. On the flip side I have 100 satisfied clients and yet I let the one dissatisfied person give me nightmares. If you can rise above such a financial crisis then perhaps mine is surmountable as well. Three cheers for Preston’s advice!!!

  • Numily Creations

    Thank you for being such an inspiration creatively and for sharing your experiences. I am a sugar flower specialist and cake artist from NY. I started my business Numily Creations almost six months ago. My biggest challenge has been keeping myself motivated. Being a successful entrepreneur and small business owner requires many qualities which definitely are not inherent in me. I’ve had to start slow and learn on my own. Luckily, I’ve had inspirational people in my life such as yourself to keep me going. I am now facing a new challenge. My husband and I are relocating to Singapore. It will be a new and unfamiliar market. My challenge now is to research the local Singapore wedding market and reach out to the wedding professionals there to connect or partner up. Any advice you can provide will be much appreciated.

  • Alexandra Jusino

    I’m an event designer. I’ve been in business for seven years. I would say right now is one of the most trying times for me. I definitely don’t have the types of problems some other posters have listed but we can all agree on is that business is slow and the competition is getting a little too cut throat out there . Definitely staying motivated because I love what I do and do it well. As the saying goes “Calm waters don’t make for skillful sailors”

  • Kisha

    Im Kisha Mitchell & my business is focused on celebrations. weddings, baby showers, promotions etc. i enjoy celebratin the joys of life. my biggest hurdle so far is keeping steady business.

  • Luz Pencyla

    Thanks for Sharing Preston!!!! You are real like every body else!!! It is very hard when you have this kind of situation,but if you fix it on time you will be more extronger than before!!!!! Right Preston??
    Thanks Again!!!

  • Becky

    I have been an event designer for seven years and the biggest obstacle I have faced is learning how to maintain a business in the slow economy and also in an industry that has no concrete instruction on how run successfully. They are so many unknowns that are constantly reveled as I take this journey of being creative and being the business. It seems that we have to make up are own rules up as we go which can be challenging. But I am maintaing, however I want to reach the lux market and do more corporate accounts that will allow me to do more profitable jobs and more creative pieces of art. How do I go from maintaing, to having a flurishing business that will allow my creative talents to reach new levels.

  • Jennifer Ward

    My name is Jennifer Ward of J. Ward Design Studio. I’m a custom stationery designer. I started focusing on weddings this year. My biggest obsticles so far is like many others consistancy as well as the opportunity to expose my business to my target bride, all while being on a very limited advertising budget.Thank you so much Mr. Bailey for sharing yourself and your experiences with us.

  • Nishaka

    Hi Preston,
    Thanks for sharing! I am the Owner & Senior Event Planner for my company in Greensboro, NC. I have been in business full time for 3 years now and have been planning events for almost 12 years. My most challenging business obstacle was helping a friend organize their event, which cost me about $6,000. I never had a contract with them to provide services. I signed the contract for the facility and the food. I also had to pay for the additional vendors used for the event. It was very devastating to me and the relationship. Trying to held a friend, it ended up costing me tremendously. This is when I learned to always have a contract signed with every client. Never to sign contracts for clients unless they have written a check to my company, I made the deposit, and asked to pay for the event with the monies in the account. I did not have $6,000 to pay for another persons event, but I had to make a HUGE sacrifice to protect me and my company name. Again, thank you so much for your honesty. We have all had some major challenges in business, but I believe we can overcome them, become wiser, and better!

  • Phyllis {My Wedding Concierge}

    Thank you Preston, for sharing your struggles with us all and being so real and approachable. My husband and I have spent the last two years building a wedding blog search engine. We’ve revised it several times and it’s gotten a lot of rave reviews in the wedding industry. Our main challenge now is to bring advertisers onboard. It’s a very novel way of advertising via iPhone and iPad apps but there are many vendors who don’t understand or are afraid of taking the leap into the unknown. Luckily, we run a very tight ship and don’t have much in overhead but still, we’d love for this business to take off!

  • http://YOURWEBSITE Ina Campbell

    Mr. Bailey,

    My name is Ina Campbell and I am a 36 year old single mother. My dream is to one day open my own event planning business. I sometimes feel that I have waited to late in life to pursue what I have relaized to be my true dream in life. I have always planned and thrown parties for my son and bridal showers for my coworkers, but never knew how to go about making it my career. I have admired your work for some time now and I am truly a fan. Can you please give me your honest opinion, is it to late me to make this change in my life? I will be enrolling in an event planning course at University North Carolina at Charlotte, but what other advice would you give to someone just starting in the business? Thank you so much.

  • Anonymous

    Thanks for sharing Preston and everyone, I enjoy reading everyone’s posts. It makes me feel less alone.

    I am the co-owner of an event design business, which has just turned 5 years old in October. Our first summer we had 3 weddings, makes us laugh now and this past summer we had 53.

    Here are a few of our challenges.

    Pricing, staying competitive while making a profit and staying in a price range that clients are willing to pay.
    Making time for family when you work every weekend (from June to Nov) and spend several evenings a week in meetings with clients.
    Mine is a home-based business, which poses another set of problems. It creates stress and really displaces my family, during my meetings.

    I’d gladly take tips from anyone who would like to pass on words of wisdom, and from anyone who may have overcome some of these issues.

    Got to run, getting ready for another meeting! :)

  • http://YOURWEBSITE Grace

    Hello Preston
    I’ve been an avid reader of your blog and an avid fan (from the UK) of your work. You are truly an inspiration to me. Enough of me been a sap and to answer your question.
    I can’t really vent about business issues since I’m only just starting up as an event designer but a challenge that I’m having to overcome is actually making a transition from my career into event designing. I come from a family of academics and achievements and worth is measured by what sort of degree you get and what you achieve with it. So naturally I got my university degree and I’ve built up a steady career with it. The challenge I’ve found is telling my friends and family that I want to leave all that behind to pursue my dream of been an event designer. I’ve had all sorts of opposing questions raised which is creating a lot of self doubt and at times I feel like I’m committing a crime pursuing my dream. So far I’ve designed a few events for family to see if this is really what I want to do and the more I get into it, the more I’m convinced that I’m making the right decision. Now the problem is working through this self doubt and trying to make my family proud and going after what I want without the guilt placed on me that I’m making the greatest mistake.
    One other challenge that I’ve found is trying to attract clients and the right client so that I can build a portfolio of work and gain more experience. There’s only so many parties I can get to do from family and friends but especially with the world economy at a teething edge, it seems no one is spending as much on decor. I’ve learned that the UK has a very close neat select of vendors and venturing out as a newbie is extremely tough. I am trying to do all I can with enrolling in flower school etc and taking nuggets from people like you and your inspirational blog.
    I would appreciate any advice you can share about your experiences starting up and how you overcame any self doubt when you were starting up. Thanks.

  • Stepping out on faith

    I am always encouraged when I hear stories of how individuals overcome adversity and yours is no exception. For the last five years I have been running an event planning company, part time. Today I was laid off from my full time job and feeling like I am not going back to working for someone else. I am not normally a risk taker but I feel like this lay off happened for a reason. Just last night I laid out a schedule of what my week would consist of if I coordinated full time. Didn’t know I was going to have to use it immediately.
    My company will continue to pay me for four more months in which I plan to use this time to build a better blog, design a newsletter, update my website, and looking into other marketing campaigns. I have made an appointment with SCORE and am making contact with vendors. My family thinks that I am crazy but I think it is that just don’t understand the need to be free to do what one loves so they are having a hard time supporting me.

  • Kristin Rockhill

    Dear Preston,
    You are an inspiration to me as I know you are to so many others in this industry. I myself have neglected the business side of event design as I get so caught up in creating that I don’t care about anything else or even charge enough for that matter and that has for sure led to some serious issues. I am at the point now where I question whether to go on or not…As a self taught florist I feel that I have come to far in the last 5 years and reading your story gives me hope that perhaps I should keep going and maybe one day achieve a truly successful and fulfilling career.

  • Yael Barkhan

    Hi Preston

    Huge fan, emailing you from Sydney Australia, although my country of birth is South Africa. I have been in the event business for a few years, focused mainly on the jewish market – Bar/Batmitvah although it seems that this market is changing and people are spending less and doing functions themselves! I am trying to branch out of this market but have very little spend to market my business, I am a one women show and business has tough of late! What are your suggestions in how I get myself and establishing my name out there – it seems most people won’t take a chance on me!?

    I look forward to your suggestions….

    Warm Regards

    Yael Barkhan

  • Navjot

    Preston,Hats off to you for sharing the most difficult times of your life. I read all the comments and surprised that people have issues just like I have. No two people share the same problem. I am in the same boat as each one of us. I am trying establish myself again. I do not know how to do the marketing in an efficient manner.

  • http://YOURWEBSITE Urmi

    Hi Preston

    Can I just speak to you pls? Please can I call you for one simple reason I want to start my own wedding planning business and I want to work under your guidance….this is my dream and I am your big fan, you are simply divine how you create magic out of nothing and everything….
    I have been a wedding planner for 5 years with some large hotels and I enjoy being involved in bringing to life most things people can dream of….at home I love making normal mundane things like a simple meal special by lighting a candle or just using diff garnishing or simply changing the lights and the music….this is thw way I live in a dream world and want it to be my career. I am in the banking industry, big money but it does not push me out of the bed…please guide me and you will shape someones career I can assure you….


  • Always Into Something

    Hi Preston,

    I’ve really enjoyed stopping by to catch the topic of your latest blog. Thank you for just being who you are. Though I’m not an event designer, I’ve been an artist all of my life. My latest passion has been sculpting with metals like wire and copper and I’ve been in business for about seven years now. I think most creatives can get kind of wrapped up in the details of what we enjoy so much so that the business aspect “no fun” is “honestly” just forgotten. I’m there right now. It’s overwhelming when I’m everything from the artist to the shipping department to the trash collector. But, I know that being the “jane of all trades” that I am, I’ll figure through it somehow. Thank you again and Stay Encouraged ;D

  • Stacy McKoy

    Hi Preston,

    You are simply amazing! Many say that I am hard to please being as detailed oriented as I am. I never go for the ordinary but the extraordinary. I am fairly new to the business and struggling to make a name for myself. My issue is “devalueing yourself.”
    Last year I signed up to promote my business via a bridal show in Brooklyn it was a big step for me because it was something I was a little intimidated to do. I paid five hundred dollars to the promoter.
    Not knowing what to expect I decided that I was going to leave the show with at least one client. So I gave away my services for free to one lucky bride via a raffle drawing.

    That was probably the worst thing I have ever done!!! This bride really shook me to the core. She called me at a minimum of 6 times a day and took advantage of me in the worst way. There is just no time to tell you everything bridezilla put me through. I would love to one day though. Long story short I devalued myself and got take advantage of big time. That experience took a toll on me emotionally, physically (I lost 10 pounds) and financially.
    Only 10 brides showed up at the show and I was immensly disappointed. I did learn alot from the experience and has since recovered emotionally at least.
    I know that God is on my side and that I will get past all the obstacles that have come my way. The entire experience left me stronger and reunited me with someone very dear to me that I had lost touch with. My cousin Kim that I called during the whole experience to help me. She was more than willing. So I got my cousin back that I love so dearly. She has been my rock a great support and I think that without this experience that i would not have reached out to her. So there is always something good that comes out of something bad.
    Preston you create magic and I commend you. Thanks for being there to listen and help.

  • Debra Biagini

    Floral Design is my third career. After many years of working as a international buyer it was time to do something more creative. Even though I am american (New York) I learned my craft here in Rome, Italy where i now have my own business.

    Three years ago I had an ilness that left the right side of my face paralyzed. It is much better now but I still look in the mirror and see my face with two parts. I notice that you have a similar condition. Thank you for showing that side in recent pictures and interviews. It has helped me to overcome feeling odd. Actually it’s now wonderful…
    I’m a woman of color, a florist and have a strong half smile like Preston Bailey. This has given me a professional edge…..THANK YOU.

    Can you tell me how you overcame being embarrassed of this condition??

    Hugs to you Preston Bailey.

    Love, Debra (DebraFlower)

  • http://YOURWEBSITE DaJor Saunders

    New to the industry!!! I really appreciate your post. I am a military wife and have lived in Japan for eight years. I have planned event for the Commanders, Squadrons and private parties. We have been living in the states for two years now and I decided to start my own business as a wedding and event planner. The obstacle that I am facing is being new to the area and establishing my own business. By starting a small business, how can I partner up or connect with other wedding professionals? There answer seems to be “NO THANKS” It is a little scary because I have a passion and love creating events for different occasions; it is a gift that God gave me. How can I move pass this? I am grateful to say that I have 1 client and she is excited to have me as her wedding planner, I’m excited! How can I gain clientele? Your words are inspirational and I thank you for it.

  • http://Iamchangingmywebsite,notyetready. Cris

    Hello Preston,
    HEllo from Brazil!
    Thank you for sharing moments of your private life with us. Maybe for some of us in the market, these words of wisdom will come in very usefully. I have one question in regard of “staff”.
    I am making some changes in my event planning business, and I am very afraid that some of my staff will keep some old habits. How do I change some habits from a staff that worked for 10 years the same way in the event business. Is it possible?
    When making changes in your own business to solve your problem. Did you maintain the same staff? I may have some problems with people that are carrying with them selves some past/wrong work habits, and that is sort of polluting my work place.
    I am changing from a 25 people Business workplace to a 6 staff work place. I am planning to start using much more vendors to work together than doing all my self. A single worker cost is becoming to high and I see its more easier to higher a free lancer to work a day than to maintain a worker for a month. (unfortunately) What are the do`s and don’ts, and the BEAWARE with working with a freelancer, or a third party / ourtsourcing company must I have?

    Thanks for all your help! You are a FANTASTIC person!

  • ELena

    What’s your honest reaction when your client doesn’t like your style or design? What do you do when you feel in your guts that your client doesn’t let you do the design the way you envisions it, and you’d rather not put your name on the design the client envisions but you are already too deep in the process to get out?

    Thank you so much!

  • http://YOURWEBSITE Jacqueline

    Dearest Preston,

    I am a student in the School of Hotel Administration at Cornell University, pursuing my passion for event planning. I have found that I have faced obstacles trying to pursue and achieve a dream that is not very common in college. I hope to one day be able to work for you and assist in the process of making people’s dreams become reality. What advice do you have or what steps should I take to make sure my goals become reality?

    Warmest Regards,

  • Savannah

    Always wonderful & helpful, Preston. Thank you. :)

    I’ve been in business for just a few months (a professional blogging and social media marketing company, particularly for wedding and event design companies) and I find my biggest obstacle to be price-setting. You’ve talked before about setting your “standards” and being “high brand / name / quality” and not being afraid to charge those prices, however, with just starting out you can’t exactly demand high prices. With a limited portfolio it’s no wonder that I have to start out lower and work my way up. Any general tips on how you can justify gradual price increases? Or even just price increases, in general?
    Much appreciated, Preston.

    Check out my pride & joy company that I blog for– The French Bouquet. FABULOUS French florist, Anne Marie Foy, is so brilliant and wonderful. Love her work and it’s a pleasure to work with her and blog about her designs. :)

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  • Karen Alston


    Thank you so much for your honesty. It is rare and refreshing! In business, everyone gloats about how great their lives are and how perfect each day is — without a challenge.

    Being an entrepreneur is difficult, lonely and full of self sacrifice. No one but another entrepreneur or someone in a committed relationship with one understands the daily up’s and downs.

    I am a small ad agency owner, I live in Washington, DC. I have been in business for nine years. I own all of your books and admire your work and dedication.

    It is difficult to charge a lot of money in this economy. I wish I could charge more. One of the things I am working on is owning my voice and public perception. I realized this year, I have achieved a great deal, but it is hard to toot your own horn. Very hard.

    Thank you for sharing. I love reading your posts, when I have time……



    Hi Preston,

    Thank you very much for this post! I run an Event Design & Floral business. We have been surviving for 6 years already which is a great blessing. I’m 24 and run this business with my sister who is 33. We still hold our day jobs but at the same time ambitiously work to develop our business!

    Challenges faced initially were typical of every creative business. Getting people to hire/trust us with their events. We started off confident of our talent and ability to provide something different. However as our projects grew albeit slowly, we faced another challenge today and that is on pricing. People say we are expensive and that we overcharge etc. We work extremely hard and by reading blogs like Think Splendid and of Sean Low’s we do charge to cover our costs obviously and a premium which basically is reflective of how much we value our work.

    But i think a contributor to this cost issue these days ironically is the immense number of wonderful wedding/party blogs out there that showcase beautiful events clearly inspiring clients everywhere to have a wedding/party of such standards. However, on the clients part there has been zero realization of whether such wants are aligned to their budget. i’m currently working to find ways to educate them about costs.

    i secretly hope couples of these beautiful weddings actually reveal their budget next to the pictures they showcase!

  • Tandy

    Hi Preston and everyone in this post,

    This particular entry from Mr. Preston has caught my attention and has given me the urge to share what I have been doing and what I have been dealing with in my business.

    I am Tandy from Singapore, I own a wedding planning boutique based in Singapore too. My business is about 2 years old and it is very challenging to be creative as an artist, many of our new clients get shunned away by the looks of our works and we are given no chance to explore our ideas in real life as there is barely a buyer in my country.

    I am quite lucky as I have been dealing with quite a number of high-profile clients who are more than willing to pay us for our works, actually Mr. Preston did one of our wedding planner’s client’s wedding in Bali, in fact the work is featured on Preston’s book titled “Celebrations”. Again, many of our clients feel intimidated upon seeing us and they choose to engage other vendors who charge significantly less and of course the quality is severely compromised.

    It is very very sad that the locals are still treating their weddings like a liability than a once-in-a-lifetime event.

  • Elisa

    Dear preston, i’ve recently started following your blog, and is the most educational and truly helpful blog. Your honest and talk about topics no one has talked about before or atbthe least in the detail you do.

    I had a little question/ advice to ask you?
    I have an event planning company and i do planning and design, thankfuly my business continues to grow; however im struggling with the actuall structure and system of the daily operations and the actual business management. I know how to put a wedding or event together, but now is not only me we have more staff and is the having a clear structure and step by step procedures on everyones envolvements, sharing of information and making sure everyine is on the same page and not stepping on each others job. What are your recomendations? How can i set up my business so that is propertly organized in order to grow successfuly
    I look forward hearing from you soon.

    Warmest regards and thank you in advance.

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