One of my first ever shoots for Rock n Roll Bride with Emma Case, May 2010

I was lying in bed one Saturday night, mulling over everything I had to get done that coming week, and my thoughts suddenly shifted to how different my life was when I was just starting my blog and business. I pondered, if I knew then what I know now, would I have ever even registered my domain? Or would it have all just felt too big, too scary and too unattainable to even try? I didn’t really have a plan or any goals for my blog when I started out, I simply wanted to write about weddings, but if I did, would it have made a difference to how things panned out?

Then I wondered if some of my industry friends had thought about this too. So I woke up the next morning and decided to ask them! I wanted to know if they felt that their businesses had a ‘tipping point’ or if things just slowly started to happen. I wanted to hear if they’d made any mistakes but most of all I really wanted to know if there was anything they wish they’d known before starting their businesses.

Full disclosure: this article is huge (6000 words!) so you might want to grab a cup of tea before you dig in. Not only did almost every single person I asked reply, but they all did so at length and with a bucket load of incredible advice. What a bunch o’ babes.

Jasmine Star, photographer

There wasn’t a single tipping point for my business, but, rather, a series of tipping points pushing me closer to where I needed to be (learning how engage with clients, finding my blogging voice, learning how to file taxes, launching a branded website, etc).  I wish it was as easy as a single moment of success, but I think that exists only in Disney movies with talking animals.

Here’s a sample blog post from when I first started my business, in February 2006:

“Why am I such a chicken? I swear I should just lay an egg to complete this metamorphosis. I mean, the chicken and I both share entities like feet, breasts, and pointed breathing orifices, so if I sprouted feathers tonight I wouldn’t be surprised. 

I need–need–to be willing to go out on a limb and ask people if I could take their pictures. I mean, I know couples who are engaged, so why can’t I bring myself to ask them if I could snap their engagement photos? For crying out loud, I wouldn’t charge them, so what’s stopping me? My fear. Of rejection. Of incompetence. Of embarrassment.

I need to do this. Just need to.”

It took about three years to get my business to a place where I didn’t fear it was on the precipice of failure. Does that sound dramatic? Well, I’m sure it does, but small business owners live in fear of their dreams dying and we’re willing to fight for every last breath.

One thing I want to clarify though…as a wedding photographer, every year I have new clients. That means I’m, essentially, trying to run a new business every 12 months. The hustle, the worry, and the chutzpah doesn’t disappear, but you simply learn how to thrust and throttle when needed.

There were so many failures along the way, but I don’t look at them as missteps as much as I look at them as ways to help push my business where it needs to be.

Here are a few thing I wish I knew before starting my business:

It might sound terribly pessimistic, but expect the worst. If you can imagine just how bad things could be–and you’re okay with the outcome–then you know exactly what you’re risking. Knowing the worst, but hoping for the best tempered my emotions when I first started. The worst case scenario (for me) was: failing at photography, going back to law school, and owning a really nice DSLR camera. Once I realized what life looked like if I failed, I was ready to succeed.

Although you don’t want to make mistakes, they’ll happen. It’s part of the growing process, but it’s important to know not all mistakes are bad. A misstep that allows you to learn, correct, or grow is actually beneficial and the more you make in the beginning, the less you’ll make later. Instead of trying to avoid mistakes, embrace each challenge optimistically and know you’re learning along the way.

Go with your gut. I’d like to think I carefully weighed all the factors before starting my business (consciously), but actual decision making is made in primarily in an unconscious way. This doesn’t mean this is bad or faulty, there’s simply just too much to digest, too many unknowns (I had never started a business before, could I really compete in a saturated market?) Innately, we want to make educated decisions, but it’s important to know actual reasons are hardly enough to cover reality. Do as much research as you can, then take a jump!

When you start a business, you want to know all your options… at least I did. Little did I realize this would only lead to the inability to actually make a decision. The more you research, the more you’ll find. This may lead to a rabbit hole of choices (been there, done that), so try to set parameters before you dive too deep.

Finally, let’s be real for a second: the daily grind of what I do isn’t glamorous. I sit in yoga pants for hours in front of my computer…I sing for my dog…I occasionally wear mismatched socks around the house. I work a ton and I photograph (professionally) on good days. Before I built my business, I looked forward to working from home with positive emotions (probably because I had never done so), but once things got going, I realized it wasn’t all pixie dust and kazoos. The emotions I place leading to or at the conclusion of an event are often the strongest because they’re idealized…it was important for me to take my perfected ideas of being self-employed and juxtapose it with reality. I wish I had done so earlier because it would have lessened the blow of sitting in solitude for hours, not having a water cooler to congregate around, and only having a co-worker with four legs.

Emma Case, photographer

I find it difficult to really talk about how or when we found ‘business success’ because for me, there are three very different strands to it. First there’s your success in building your business (in terms of your brand, your reputation, your product, your experience, your audience, your enquiry stream, your industry community etc) and then there’s financial success (supporting yourself and the business, and making it a viable living in the eyes of yourself, your family and your accountant). Then there’s the strand of how all of these things effect your overall happiness.

You could have a wonderfully successful business, financially, but you can still be unhappy. Or you could be working 24/7 to achieve success in terms of your reputation but again, this doesn’t guarantee happiness. We’ve had various points in the business where all three strands have flourished but now we realise that our goal is to simply be happy so we’re working on the balance we need in every part of our business to achieve that.

In terms of tipping points, I think we’ve had various ones in the past five years. Year on year we have had small achievements and discoveries in all areas of our business and although we were pretty lucky in terms of the market when we started and the opportunities for natural growth, I think the main thing that has been on our side has been the opportunity to make mistakes and learn from them over time.

I think around the three year mark our overall confidence in knowing the job emerged and with that comes a security and confidence. I also think that that three year mark is when I started to really know who I was and what I wanted to say with my work and there was also a security and confidence in that too.

If I’m totally honest, being financially stable and running the business as a ‘business’ has been the slowest burner and the hardest thing for us. It is still something that we are learning but I guess that’s the thing with having your own business, you never stop learning and those tipping points never stop coming.

I also don’t think that one day you just wake up and your business has ‘made it’. You’re never able to just sit back and relax. It requires constant attention. Yes you might have periods where you are getting bookings quite comfortably, or one year you might find yourself financially better off than others, but it’s kinda like riding a bike: if you stop peddling you’re just going to stop moving.

I think the biggest bit of advice for any new business (especially wedding photography or blogging) is there is no quick fix. I think anyone starting a business now is in a position where they can actually see the ‘end result’ if you like. They can see others who have made a successful business so they can see where they want to get to, and a lot of the time they can also find out all the practical steps that got the successful ones to that point. But what’s missing from that formula is time. The journey, the mistakes, discovering who you are, building your reputation, building your readership, building your experience… just everything that comes from you and you physically experiencing it for yourself.  That, in my opinion, is what will elevate you and your business.

I’m not sure if there’s anything I wish I’ known before I started my business. We’ve made loads of mistakes along the way but sometimes a mistake offers you an opportunity that you might not have had otherwise. There’s loads of stuff that would have saved us a lot of time or made things easier if we’d known about them at the start but I think sometimes you’ve just got to roll up your sleeves and get on with it yourself. A big part of knowing or learning something is actually having that journey and discovery yourself, and we’ve enjoyed every second of our process.

Paul Jarvis, web designer and writer (you really should read his latest book, Everything I Know too, it’s awesome)

In my first year of business (almost 20 years ago), I didn’t know anything. I was fresh from dropping out of university and although I had some clients, I routinely got screwed out of money, walked all over and made to do work I didn’t enjoy. I wouldn’t do anything different though. I think of working for yourself as a very long game where you have to learn from your failures… I still don’t know what I’m doing, but I’m learning. And I enjoy the process of learning.

Entrepreneurialism, especially when it involves art or creativity is measured in years and lifetimes, not days or weeks. The tipping point for me was realizing two things. The first was that since I was the boss, I could let my business be guided by what I actually value (and say no to anything I didn’t). The second was that I’m responsible for the work I put out into the world—so if I couldn’t stand behind it, then it wasn’t worth doing.

Gala Darling, writer, speaker, magic maker

You know, the thing that transformed my business most was moving from Australia — where blogging was only just getting off the ground — to the USA, where it was beginning to be embraced by the fashion industry. I think I moved at the right point within my career, too: I had been blogging full-time for a year and a half, I had a column in Cosmopolitan magazine, and I had really started to build a name for myself.

It was all a total surprise to me: I had no idea how different things would be in New York City. I had been there for less than a week when Louis Vuitton came calling and invited me to brunch with their director of marketing. Everything really began to speed up from that point. A while later, I met the woman who would be my future manager in a juice bar. Did I mention recently that I love this city?!

I suppose the moral of the story is that sometimes you have to go to your customer, rather than waiting for them to come and discover you. A super-niche business in a tiny town is always going to be a hard slog. There’s a reason people move to big cities: the opportunities are unparalleled.

I tried about a trillion things that didn’t work. I had an eBay store, I sold t-shirts, I sold desktop wallpapers, the list goes on. Even today, I try things that don’t have the response or impact I was hoping for. But that’s okay, and crucially, it’s all part of being an entrepreneur. Fail quickly, then move onto something else. Your next great idea could be just around the corner, but you’ll never know if you don’t give it a shot!

The only real, tangible thing that I think would have helped me when starting my business is being able to use a camera more skillfully! I’m glad no one told me how much hard work it was going to be. It might have put me off! The thing that has made the journey enjoyable is that I absolutely love what I do. When you’re adoring it every day, the days — and years — just fly by.

Sophie King, headwear designer, Crown and Glory 

I don’t really feel like there’s been a ‘tipping point’ for Crown and Glory as such, and for that I’m really grateful, because it’s allowed us to grow at a steady pace. I always worry that businesses that achieve overnight success or get to a ‘make or break’ point are going to struggle because they might not be proper equipped to adapt that quickly.

You see so many businesses having one amazing piece of press, or getting something onto an international celebrity overnight and then they can’t cope with the response from it. Of course, with proper planning, this sort of exponential growth can be managed effectively, but slow and steady has won the race for us and my blood pressure is glad for that. It took me two years to reach a point where I was able to go full time in the business and I’m really glad I held off until then, no matter how much I wanted to throw caution to the wind at times!

We tried so many things that didn’t work, but as long as I make sure at the end of it I take stock and draw something from the experience, I don’t have regrets. Most memorably, last year we tried to get a project off the ground that transpired was just not a good fit for the business at all. There was going to be a lot of risk for us to continue forward with it, and there were just too many people involved that really didn’t need to be. But although it was a super stressful and expensive time, I’m so glad we took the chance to explore the opportunity but had the sense to call it a day when we did. I genuinely think this is because we’ve grown steadily and learned as we’ve gone along.

Had the same opportunity been presented to us in say, year one of business, I think my judgement would’ve been clouded by the flashy names and bright lights involved and the end result could have been a very different story indeed! Ultimately, you have to trust your gut with these things. Learn quickly how to determine the difference between fear and intuition; fear will hold you back, intuition has got your back.

There are a lot of people out there that are looking to make money off your inexperience and who will try to knock you down for their own gain. I wish I’d known this when I started the business. My advice to anyone just starting out would be to get wise to those jokers, quickly! I wish I’d surrounded myself with like-minded peers earlier on as it can be pretty lonely climbing on your own. You’ll also get way further by approaching issues with positive energy and good vibes than bitching and moaning. Finally, don’t constantly compare yourself to others! Your journey is different to them and someone else’s success should not define yours.

Rachel Southwood, founder, Wedding Ideas magazine

I was very fortunate that we hit the ground running on the launch of Wedding Ideas. I have been in media since the age of 17 so it’s an industry I know well, and I was fed up with launching successful products for other people… The biggest challenge was finding a gap in the market and filling it with a product with a USP. Because wedding magazines until then had all been bi-monthly and big glossies, I identified a market for a practical, down-to-earth budget-friendly wedding magazine and went for it!

Of course the team were (and remain) pivotal to everything I do. While people place their business with a product because it works, as important is building relationships, especially in industries like ours where everyone knows everyone else. While weddings are clearly big business, it operates a little like a cottage industry, one which is made up of many small businesses. That keeps it innovative and creative, I guess.

My biggest asset but also my biggest problem is people. The challenge for me as the company grew was that the odd round peg didn’t fit a square hole. If you don’t function as a team you simply don’t function! Since taking over from my former business partner in 2008, I set about creating a team that I knew would be passionate about the brand and each other. This mainly meant recruiting from outside the media world. You can teach people how to write but you can’t teach them loyalty, passion and creativity! Also, our geographical location (Taunton, Somerset) helps a lot!

I have had a couple of big disappointments in my time at the helm of Giraffe Media, the biggest of which was closing House & Home Ideas magazine in 2007. It was a heart-breaking decision because there were redundancies to be made, but business is business and it was dragging the Wedding Ideas brand down. Fortunately the art editor of the title came back to Giraffe a few years later.

What do I wish I had known before I started in business? That you can’t do everything yourself! Delegation is key, and I have built a team around me who complement my skills. Where there are gaps in my knowledge or skillset, they exist in other people. The other lesson I learnt is that if you’re good, you get copied. ‘Me too’ products drive us to be bigger and better but they are a fly in the ointment, for sure.

Charlotte Balbier, dress designer

In a way, the first year of any business is one of the easiest as everything is so fresh and new and you don’t have anything to compare it to. I think year two and three are the hardest as this is when you really have to prove yourself, establish your brand and not to mention make some money! My third year was then I really started to see a difference on our bottom line and our turnover and profit increased dramatically, but it wasn’t until year four that the brand profile really raised and started to get recognition.

I worked very hard the first three years to put the foundations in place and slowly build the brand and our customers base. Once this was solid I really upped the PR and marketing. I did a kick ass photo shoot and had a really creative team. I worked with a Condé Nast stylist and photographer, blew the budget on a model and an amazing location and had a very strong collection of gowns. This combined, got everyone’s full attention and I have never looked back.

When I think back to when I was starting out I do wish that I’d known at the beginning that that not everyone is as passionate and positive as you are about your brand and business. Even now, after 10 years, I am still (if not more) positive and passionate about my brand and the bridal industry but not everyone you meet with be. You have to not let these people affect you, your business and your drive. Believe in yourself, your business and brand and others will too… it’s all about being positive and strong.

Abigail Warner, stationery designer

For me it was a combination of events that really kick started my business, but the real tipping point was being accepted to exhibit at the now defunct The Designer Wedding Show in Spring 2008 (I was refused the first time I applied in 2007). That show put me in front of my perfect clients, the bridal press, bloggers and planners. This was all in the first 12 months, 8 months after I launched, but it wasn’t until the second show with them in Autumn 2008 that I think my business turned a real corner. I learnt so much that summer: making my product offering very clear, honing my pricing and offering products that complimented my skills and style.

Of course I did plenty of things that didn’t work though! But one of my most *brilliant* (ahem) ideas was back in 2009 when the DIY trend started kicking off and I offered a service called Little Lily, which was a make-your-own-version of my best-selling Agatha collection. I invested lots on photography, updating my online shop and with all of the products themselves as well as so much time on PR and it B O M B E D. It just wasn’t what people wanted from me. If I’m being honest, I was trend whoring, trying to be everything to everyone instead of concentrating on a) what I was good at and b) what I enjoyed doing. The whole thing just lacked authenticity, hence it failed.

When I first set the business up I was working 80+ hours a week but telling myself it wouldn’t be like this forever and eventually it would be half of that – that’s what everyone does right? But after working (and playing!) really hard for a couple of years I finally realised that I was pushing myself too hard and that working basically two full time jobs didn’t make my business twice as good. In fact I was a lot less productive because I was so exhausted.

So 18 months ago, some five years into my business, I finally learnt that the reality is you’ll never be ‘done’ with your work, you’ll never finish everything on your to do list, answer all your emails or have the perfect design every time. Realising this was so freeing and I’ve never been happier, or busier with great clients AND I’ve never spent as much time with my friends and family. I just wish I knew this when I first started!

Shauna Haider, graphic designer, Branch

Although I only launched my design studio, Branch, in September 2013, I’d been freelancing for six years and so from the day it launched, our bookings were consistent. In the past six years I’ve learned a lot about what works and what doesn’t.

Part of the secret to getting regular bookings is consistency. Constant interaction across social media channels, using matching internal documents, a branded email signature, a media kit explaining what your business stands for, a custom price sheet and a welcoming, user friendly website all play into the public perception of your business. Potential clients want to hire businesses that look like they have it together. They want to be able to trust that you’ll do a good job right out of the gates and a professional image helps with this perception.

At Branch, we’re still tweaking little details but one thing we believe in as our business continues to grow is to treat everyone with the same grace and respect that you’d treat a client. They’ll remember those interactions, even if it’s a response to their tweet or a friendly hello at a party and may call you one day. We send out quarterly print promos to fans and are starting a newsletter soon. Anyone can sign up. By opening the doors to your business and being welcoming, you’ll stand out. Good manners never go out of style.

Laura and Emma, vintage wedding dress shop owners, Fur Coat No Knickers

It was really in  the second year of running our business that we decide to commit to bridal and become appointment only to try dresses on. Then it was a gradual build and word of mouth that got our name out there. We gave the best service we could and were helped along by amazing blogs like the fantastic Rock n Roll Bride.

Gradually we got a bit bigger, got two fitting rooms, and we started to realise the gaps and restrictions of the vintage dress sizing. So we set about designing our own collection based on vintage styles but that could go up to a UK size 22. We quickly realised we can’t do everything at once so we are now adding new dresses to the collection slowly and steadily.

Almost 6 years on we are still building Fur Coat No Knickers and only just now we have won our first award.

In terms of mistakes, we’ll it just took us a while to figure out our strengths and USP. Our original little shop was aimed at theatre and film costume but we soon realised our taste in dresses and accessories and our skills in fitting and looking after people were more suited to brides and vintage lovers. Since switching over to 100% bridal we’ve never looked back.

We wish we’d know about all the hidden costs that come hand in hand with running a shop when we started out. All your money goes back into making it better and there are lots of sleepless nights. But despite the long hours and worry we wouldn’t change it for the world. We just feel lucky we are in it together, we are always there for each other to share to worry, bounce ideas off and have a glass of bubbly with. We never don’t want to go to work.

Elbie Van Eeden, hair and make up artist

My tipping point was when I stopped being scared of my abilities, when I just threw myself out there, whether people liked it or not! I guess you have to be willing to be visible. Know what your target market is, and work with similar minded people to produce something ‘you’.

When I started posting more images of my work on Instagram it really helped in getting myself noticed, and I got more and more hair enquiries too. How long did it take? Around 6-8 months after I quit my job, and I’m still learning!

Of course certain things work better than others. I try to do a lot of research before I make a commitment, so thankfully most things worked out to some degree! What doesn’t work is when you sit back and expect things to just come your way. You need to stay proactive.

When I started out I would have liked to have known the benefits of working out the journey of each choice I had to make. If it doesn’t take you towards your goal, step away from it, and take another route.

Christina Looker, photographer, Made U Look Photography

I would have to say that the main thing that really made Made U Look take off and start to get consistent bookings was only featuring (on our own blog, wedding blogs and in magazines) the work that we wanted to do more of. This helped us build steady bookings, but more importantly, of weddings that we were really excited to shoot!

Being featured in places like Rock n Roll Bride really helped in getting our name out there to more than just the locals and really broadened our clientèle.

There were plenty of things we tried that didn’t work for us. We did try the local bridal shows, which wasn’t as much as a success as we would have hoped for. We found ourselves putting in so much time and effort, then finding that we were only booking a few local weddings from them.

Before starting Made U Look I wish had known that being a professional photographer is more of a way of life than just a profession. You really never stop working or thinking about it. We wish we had known about this beforehand so we would have established better boundaries between our personal life and the business life.

Lucy Ledger, stationery designer

For me it took around 6 months for my business to start making a decent profit, which is super quick but I was careful not to launch too soon. I spent 18 months prior to setting up the business refining my style and researching ways to promote my work and connect with the right people. I guess you could say I did my research and although at times it felt frustrating, when it came to the launch I had a full product line, a completed website and I really hit the ground running.

I tried plenty of things that didn’t work! As a creative you always come up with new ideas and they all seem great at the time but you soon find out what’s not working. Mugs, homeware and anything like that really doesn’t work unless your designs are licenced on a large scale – if it’s more a ‘vanity’ item than a product that makes money and you have to ask yourself why you are selling it. The bravest thing to do is to admit to yourself that it’s not working and withdraw the product in question. You always have to be thinking as a business owner first and an creative second.

There are so many things I wish I’d know before I started out!!! Where to outsource my print was one of the biggest. I had around two years of trial and error before I finally found a great printer that I now have a fantastic relationship with. Really, I would have loved some guidance of any kind – I felt very alone in the stationery industry until I met Abigail Warner who was a breath of fresh air. It was though this and sharing our stories that we set up PaperGirls to help new stationery designers. I wish something like this had been around when I started but I guess finding your own way and making mistakes makes you a stronger person and a more accomplished business in the long run.

Kirstie Taylor, bridal headwear designer, Flo and Percy

The main change from moving from a very small independent designer to a larger one was making my business SCALABLE. Originally I was making one off original vintage designs when no one else in the market was (we were the first to start using vintage jewellery in hair accessories back in 2005) and I couldn’t keep up with the demand. Turning those pieces into repeatable designs by manufacturing my own components, hand finishing them here in a small studio and selling them wholesale to bridal boutiques, turned my business from selling 100 pieces a year to selling over a thousand a year, that was a massive tipping point!

I am always looking forward, as a business owner you have to constantly come up with fresh new ideas and how you can drive your business forward and not forgetting that magic word: Scalable!

We tried wedding fairs in the beginning, and although they weren’t unsuccessful, the time out of the office, cost of stand, marketing, time for preparation did not add up. We prefer to use our marketing budget on advertising and other opportunities where we can reach out to more brides nationally. Local advertising does not work for us and we would rather spend more money and reach a larger national audience. Sometimes its difficult to evaluate what works and what doesn’t and as long as it’s cost effective we are always open to new options and trying things again that haven’t worked previously.

I am glad that I was quite naive when I started the business, I have enjoyed the journey and the learning process and I am still learning everyday! Don’t be afraid of your ignorance and don’t be afraid to ask help from fellow professionals in your industry. Thats what makes the world go round and I have mentored many people in their business start ups.

Maybe I wish I had know everyone in the bridal press though!

Christine Taylor, creative director, Choccywoccydoodah

The first year that Choccywoccydoodah was born it took £7,000. It was an appalling turnover but gave us the confidence to believe that if strangers were prepared to give us £7,000 for what we did, and were happy, they would pass on recommendations.

We were right. One happy customer can bring, on average 5 more customers. Keeping customers happy makes for brilliant growth, maths and turnover. Eventually.

In any business, you need courage, patience, tenacity and the ability to endure poverty with good grace, to get started. You also need to recognise when an idea is a bad one and graciously give it up. Part of the process of starting up in any business is getting it right. Cocking up is so important, so long as you learn from those cock ups, don’t stubbornly repeat them until you’re broke, isolated and foolish.

Be proud of your achievements, be proud of your sacrifices, be proud of your mistakes. Never be arrogant. Accept your responsibility. If your business fails, it is your responsibility. Somehow, you got it wrong. Similarly, if it works, that’s because of you and your cleverness/good luck/stubborn determination.

I wish that before I decided to set up my own business, I truly understood that:

I would never be able to take time off sick. Ever.

I would never again be able to take 2 weeks holiday. One week is as long as I can be away from the business before my mind explodes with anxiety. And I always take my computer.

That no-one but me would ever be responsible for my income. Or the income of my employees. If I don’t earn it, none of us get paid. HUGE responsibility.

I work from Monday to Sunday. 365 days a year. There is no freedom in working for myself. Unless I employ you, whereby I pay for your holidays, your sick time, your wages. I make certain you work reasonable hours and when you leave work at the end of the day, you don’t need to think about it until you’re back the following day. I, however, think about it, about you, about the customers, about your colleagues, ALL the time.

It is tough.

However. I am tough. My lessons have been learnt the hard way, through experience.
I love what I do. I love the people that are with me on my journey. I love my Doodahs, my customers, my world that I have created. I love that I can be at work all the time because I love my work. I never looked to earn a quick buck, and in that, I’ve been enormously successful.

For me, the joy has been the journey, the adventure, and the achievement of establishing a tiny brand that has global recognition. I would not swap my life, change my life, or how I’ve chosen to live it. But – I am very very tough.

Last, but best bit of advice – only ever fight the battles you know you can win. The rest is compromise.