How to know when it’s time to quit ~ four questions to answer honestly.

It is so much easier to start something than it is to finish, AMIRIGHT?!

I’ve come up with business ideas on a Saturday, been all in by Sunday, and have fully given up by Friday.  I have been the college drop out.  I’ve quit jobs before I really gave them a fair shake.  I’ve experienced my fair share of quitting but looking back I don’t have regrets.  I am convinced that quitting the things that are wrong for us can actually be the most productive use of our time. 

My Dad once told me a parable about a man who places his ladder against the tallest wall and begins to climb.  As he’s climbing, he is met with great resistance. People constantly shout up to him, “there is nothing behind that wall” but he keeps going.  For years he climbs, and when he reaches the top he is a very old man.  He looks over the top of the wall and sees emptiness. To his left and right he sees other much smaller walls that lead to lush gardens and green pastures, but his wall has led him to nothing and now he is too old to climb another.   

We live in a society that praises the endless hustle.  We revere the people who are so dialed in on their dream that they keep pushing to great levels of success even when everyone seems to be screaming “you’re going to poop the bed.”  But these people are the lucky ones.  Most of us don’t have the luxury of knowing exactly what we want to do when we grow up. Even when we’re 35 many of us are still left scratching our heads and waiting for that thing to click on like a light bulb. Guys, there’s probably never going to be a light bulb.  It’s OK to change our mind about things and it’s OK to take a few swings before we hit that home run, but eventually, we’ve got to choose what we want and go all in for it.   

In truth, most successful entrepreneurs never have that moment where the sky parts and angels float down singing “you’ve found the thing you are supposed to do.”  Many great success stories involve a lot of pushing through resistance, overcoming imposter syndrome, and wanting to quit but forging ahead regardless. 

Going all in on a dream without any promise that it’s going to work out can feel terrifying, but if you have chosen the path of the entrepreneur, you’re already braver than most.  You know a little healthy fear never killed anyone, and you give yourself permission to feel the fear and do it anyways.

So how do you know that your ladder is against the right wall?  You can start by taking imperfect action and opening yourself to the growth that comes in the process. You should be willing to pivot wherever necessary and also, when the time comes, willing to quit.  You don’t want to spend your whole life pursuing emptiness.  Quitting the wrong things will free up your time to go all in on the right things and you absolutely should quit that wrong thing asap. 

If you are currently in a point of resistance and considering throwing in the towel, here are some questions you can ask yourself. (Spoiler alert: chances are you probably shouldn’t quit.)

Would you still do this if you knew it wasn’t going to make you rich?

Money is a great motivator but it should never be the only motivator.  If you knew your business would keep a roof over your head and food in your belly, but probably not help you afford the dream home in Maui, would you still do it? If you knew your business was going to help others, or solve a problem in the world but only provide you a modest income would that be enough to keep you going?   All entrepreneurs should have a ‘why’ and this ‘why’ should be enough to keep them going when they are inevitably met with resistance. There is nothing wrong with having lofty money goals and wanting all the freedom that comes with a fat bank account but if the money is the ONLY reason you keep climbing, you might be climbing the wrong wall.  Still, this doesn’t mean you should quit. It means you need to find a ‘why’ that is bigger than your bank balance.  Pivot your business into something where the real reward is filling a hole in the world and embrace the money that comes as a bonus.

Have you REALLY given this thing a fair shake?

There’s a distinction between quitting the moment you feel the least bit of discomfort and pursuing the wrong thing for way too long.  You are going to have to get very comfortable with hearing ‘no’ if you are going to be an entrepreneur. Hearing ‘no’ is a good thing, it means you are narrowing down on your messaging so the customers who aren’t for you can fall away.  Hearing no is not a reason to quit as long as you are also hearing yes.  If there are people who are picking up what you’re putting down you are on the right path.  JK Rowling took 6 years to write the Philosophers Stone, and was rejected by multiple publishers, but her kid LOVED the book so she kept pushing.  If you have been at it for six months and are wondering why you are not a famous billionaire yet, you’ve got to give your head a shake.  I know we sometimes hear stories of entrepreneurs who launch a product and within a year are a household name, but they are NOT the norm.  The normal path to success is marked with ample failure, pivots, and persistence.  So if you haven’t yet given it a fair shake, you are definitely not ready to quit. You are probably just getting warmed up. 

Are you seeing progress?

Slow progress is still progress but if you have been at this for a while and are more or less in the same place that you were in five years ago, the universe might be trying to tell you something.  Some ideas may need some tweaking and some might just need to be flushed down the toilet.  Just as you should never be in business solely for the money, you should also never be pouring yourself into a business that gives you nothing in return.  If you are not seeing progress but see others in your same realm making huge strides, take a good look at what they are doing better.  Be honest with yourself and be willing to give up the things that aren’t really working.  Look around; if you are a total pioneer in your pursuit, you are either on to something completely genius or absolutely terrible.  If it’s been years of no progress, chances are it’s the latter, but that still doesn’t mean you need to quit. Use the points of resistance to pivot yourself into a position where things start to flow.  You could be headed in the right direction but just need to be moving towards it from ten paces to the left. 

Do you love it?

This circles back to ‘would you do this thing even if you knew it wouldn’t make you rich.  Loving something doesn’t mean you never have moments where you hate it.  When you pass from this earth will you be able to look back on your life and see that your days were filled more with joy than despair?  All you really have is the now, so if you are currently pursuing something that fills you with dread on a daily basis, tread carefully.  If you are miserably slogging along to one day reach some arbitrary financial goal or gain some sort of notoriety, you have chosen the wrong wall to climb and you should most definitely quit, GTFO and don’t look back. Keep on pushing till you find that thing that makes you want to jump out of bed (almost) every day. It’s out there and chances are it’s right behind the wall that was right in front of you all along.         

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The fall of Nasty Gal and why slow growth is the key to lasting success.

Maybe you’ve heard the story of Nasty Gal vintage?  In 2011 Sophia Amoruso started a little vintage shop on Ebay and it grew like wildfire.  I remember watching her success in awe as I was also running my first vintage shop back then.  While my shop was steadily puttering along hers was taking off like a concord jet. I was blown away by how quickly she rose from a San Francisco hipster slang-ing old clothes to the Girl Boss she would come to be known as. 

In the beginning her fan base, like mine, was small and dedicated. She had a five star rating and regularly interacted with her fans on social media but within a few short years Nasty Gal would become a multi million dollar business and land Sophia on Forbes richest women list.  Even though we had started in the same place, she had grown so much faster.  I was in awe (and a little jealous) of her rapid success but I failed to realize at the time that lighting fast growth can be a double edged sword.  When a tree grows too quickly it does not set down strong roots.  Those are the trees that are often fall when strong winds blow. 

As Nasty Gal exploded in popularity, product quality started to decline.  Sophia stopped picking vintage herself and hired a team to do it for her.  The company also began selling mass produced fast fashion that customers would often complain of the quality, or lack thereof.

 The last time I looked at the reviews I was horrified, it was not the business I had once looked to for inspiration, it had become a monster.  Recently the company went bankrupt.  Luckily Sophia was able to get out with a cool 20 million, but considering the fact that the business had once been valued at over 200 million, it’s kind of a sad ending.  

I’m not trying to slam on Sophia, I surely would not have done any better if given a rocket ship to success in my early 20s. What she did is still so inspiring to any of us vintage sellers out there. But I do look to this story when I get down on my shop for growing so slowly. In many cases slow and steady growth can actually be a blessing in disguise.

It costs four times more to gain a new customer than it does to keep a customer you already have so wouldn’t it make sense to nurture our small customer base first and foremost?  So often I see other businesses like Nasty Gal rise to huge levels of popularity and stop being the brand that earned them that popularity in the first place. 

Even as I grow, I hope to never forget where I started from. There are a few core values that make my business what it is and are things I would never be willing to compromise on for growth.  I would never put out poor quality products to make a quick buck.  I would never exploit underpaid workers to make my products.  And I will never knowingly do something to make a customer feel small or unimportant.  As your business grows I encourage you to ask yourself some key questions;  What matters to you? What do you refuse to compromise on as a brand? And how can you make the customer base you do have feel valued? Growing slowly will allow you to hold on tight to these values as you come into your own.

I’m still in the dawn of my business and can just now see the sun peeking over the horizon.   My shop is still just a sweet little baby that I get to feed and love and nurture.  I haven’t been swept away in the chaos of success and so I get to define every day who I am and show up authentically.

Would I trade my little baby business for Sophia’s 20 million dollars? Maybe, in a moment of weakness I would, but that doesn’t mean I’m not still grateful to be where I am.

If you’re just starting out and slow days have you feeling down, remember, you’re putting down those thick strong roots. Spend time nurturing the relationships you are building one at a time. Be generous with people and give 100% of yourself to whatever audience you currently have, even if its just 10 face book friends and your mom, businesses have grown from less. Show up everyday from a place of integrity and watch that business slowly and purposefully grow into something that will stand up against even the strongest winds.

Five FEMALE entrepreneurs who achieved greatness after struggle. A closer look at how humans often fail into greatness.

It’s not hard to find stories of entrepreneurs whose first ideas flopped before they had their breakout moment.  I especially get fired up reading stories of female entrepreneurs who kept pushing through resistance towards their dreams. As females, the way we appear outwardly to the world can feel so important, but all great female entrepreneurs had to at some point stop caring about how other people perceived them and just keep fearlessly pushing forwards. 

Many great success stories often come on the heels deeply vulnerable moments.  When we forge our own paths as entrepreneurs, we might have moments of looking a bit stupid, or we may experience full blown failures that make us want to quit.  Still, avoiding failure at all costs is not only unreasonable but also robs us of life’s greatest teaching moments.

Like most entrepreneurial kids I did the lemonade stands, I went door to door raking leaves and shoveling snow, I babysat the entire neighborhood and did anything I could do to earn a dollar without having to get an actual job.  I recently found a picture of my very first clothing business.   No, not my first etsy shop, that also failed, this was way earlier.  See that pointy hat on my head?   A literal dunce hat made out of upholstery fabric from a forbidden book of samples that my mom kept in her sewing room. I didn’t technically ask to use the samples and I was definitely not allowed to use the sewing machine but one summer day inspiration stuck and my first physical product was born.

You could say this business was a failure because in almost every way it was.  But rather than decide I’m a terrible designer who has no business making garments, I learned some amazing things that I’ve carried with me to this day.  I learned how to thread a machine and sew a straight stitch.  I learned that having people tell me “no” is not the worst thing that can happen, nor is looking stupid.  I learned that I love creating things with my hands and that will forever be my happy place.  I learned that people will buy silly things just because they like the person selling them and I began to imagine how easy it would be to sell things that were actually good.  This very short-lived business of terrible hats was a gift, it was a spark that ignited decades ago, and that has smoldered in me all these years.  It was the very first failure (of many) on a path that has led me to where I am today.

Today my business is still a tiny baby and so I imagine I will fail many more times as I go through the process of raising this baby into a woman.  I’m positive that at some point I will look back on where I am now and cringe, but I’m ok with that.  If we aren’t cringing at our earlier selves, we are not progressing at our craft.

We needn’t look far to find examples of entrepreneurs who have faced adversity and risen to greatness, but I wanted to dig a bit deeper into the female side of things.  There are some household names that immediately popped out at me but are also some lesser known individuals whose stories have inspired me.   So, here’s a look at some ladies who have achieved greatness and have done so not in spite of failure, but also because of it…        

J.K. Rowling

This is one of my favorite rags to riches stories.  Not just because I am the biggest Potter-head of all time, but because this bad ass woman was a single mom on government assistance when she began writing the epic series that would make her a billionaire. It took her six years to write The Philosophers Stone but she persevered, finished her masterpiece and then proceeded to be rejected by 12 different publishers.  There were many points in her journey where I’m sure she felt like an epic failure and she has even spoken publicly about a brief period where she had considered taking her own life, but she kept pushing and eventually became the first writer (female or not) to earn a billion dollars from her work. Boss babe 101.

Cathy Heller

This beautiful soul has been hands down the biggest source of motivation in my own pursuit of entrepreneurship.  She moved to L.A. to become a recording artist and ended up being dropped from not one, but two record labels.  Rather than wallow in despair at a failed music career she created her own music career by selling songs to businesses for huge royalties and built a six figure course teaching others how to do the same.  But she didn’t stop there, she has since gone on to start the “Don’t Keep Your Day Job” podcast (get into it), write a book and build a coaching empire that brings in 8 figures annually.  Not only is she crushing it financially, she now gets to help other entrepreneurs learn from their failures and rise to greatness all while doing their life’s work.   

Madame CJ Walker (Sarah Breedlove)

I first learned about this QUEEN way back in the day while attending hair school.  She was my first peek into the world of female entrepreneurship and living proof that we truly are in the drivers seat of our lives.  This icon was born to  former slaves and by the age of seven she was orphaned.  Left to grow up alone in a world where she faced incredible limitations, not just as woman but also as a person of color, she married at 14, became a teen mom and was living in poverty when struggles with hair loss sparked a calling within her. She had been born into a life that had set her up to fail, but instead she would go on to become the first black American female self made millionaire.  How did she do it? Pure hustle.  She created her own hair growth formula, hit the pavement and sold it door to door.  This would eventually lead to her own hair empire and a netflix special a century after her death.  Talk about leaving a legacy!

Jamie Kern Lima

This amazing woman is the founder of IT cosmetics which she ended up selling for 1.2 billion dollars.   I’ve recently listened to a few podcasts where she is graciously details all the failures she had to endure to achieve such a high level of success. With every penny invested in a business she believed would change the face of the beauty industry she fearlessly knocked on doors and heard all the no’s before her big break would happen. When that break finally did come in the form of a 12 minute slot on CVS, she was down to her last $1000 and one slip up away from total bankruptcy. In spite of all the experts urging her not to, this brave woman allowed herself to to show her bare skin and represent for those struggling with rosacea on national television.   Real woman finally saw a makeup brand representing faces that looked like theirs, these same women fell in love with the brand, and the business went to the moon!

Suze Orman

Hers has become a household name, but not everyone is familiar with her humble beginnings.  At the age of 29 she was working as a waitress making $400 a month and managed to scrape together 50 000 to open her own restaurant.  Sadly, that fifty large ended up badly invested, she lost every penny and was forced to close the restaurant.  Wanting to help others avoid similar situations she educated herself on financial management, scored a job at Merrill Lynch and has since appeared regularly on Oprah and written books on financial literacy with an emphasis on helping women gain financial independence.   Hers is an inspiring rags to riches story featuring female empowerment if there ever was one. 

There are so many other stories that didn’t make this list.  Perhaps you’ve seen success stories of women killing it posted all over Instagram and perhaps it’s those same success stories that make you feel unworthy to start your own thing.  Just remember, anyone doing anything great most certainly has some form of failure behind them.  Don’t compare your mess to someone else’s curated feed. Just don’t. Give yourself the permission to do that thing that makes you really lit up but also a little bit terrified. Make messy things, wear stupid hats, persevere and allow yourself to fail into greatness.

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Don’t trade perfection for progress ~ perfection is unachievable and progress only comes with imperfect action.

The first thing I ever sewed looked like a grade two craft project.  The first thing I ever cooked tasted like burned garbage.  The first thing I ever wrote was a poem about Kurt Cobain (and it was bad).  The first person I ever dated was a certifiable f**k boy.  The first haircut I ever gave was a disaster. The first bleach out I ever did was with actual kitchen bleach (sorry Amanda). 

Nothing I have ever become good at was an automatic win.  Nothing.  And if we’re truly honest with ourselves we will see that is a common thread in the human experience.  Any craft takes time to perfect, we’ve got to make a few bad choices to figure out the right ones (hello my entire high school experience).  Even people who are born with immense confidence in their abilities probably look back on their earliest work and cringe.  And that’s how it should be.  What are we here on earth for if not to grow and learn?  

Humans are social creatures, we long to be accepted by our peers and the human condition is often to reject that which is not familiar.  This is why we look to the doctor, lawyer and corporate exec as barometers of success.  They fit into a format that is easily identifiable, replicable and proven.  They don’t even have to be good at what they do, just the fact that they have obtained that position is enough.   There is a safety that comes from choosing a path that our peers approve of, but we can’t all be doctors lawyers and corporate execs.  If we were, our world would be lacking…we need artists, entrepreneurs and visionaries. 

The path of the artist is often paved with self doubt.  So many people, myself included, can become so paralyzed by the fear of failure that we fail to take any action at all.  We are already so far out there forging our own paths, how scary it can feel to do anything that may draw even more attention to our radical selves.   Rather than risk looking stupid or making something bad, we stay in our lanes and remain consistently mediocre. We use all the pretty crayons but are careful to color in the lines.   

I acknowledge that it can be terrifying to embrace failure.  We don’t want to end up with pie on our face (and an empty bank account) but maybe our journey as artists depends on taking those risks.  Maybe taking a pie to the face every now and then is just what we need to keep us moving forwards. 

I have friends who have put off starting their business for months because their logo wasn’t perfect. Ask yourself this, have you ever been about to buy something online and stopped because the logo wasn’t to your taste? We let ourselves get so hung up on insignificant details that we fail to take any action at all. If there is one thing I have learned in my 35 years, its that the greatest breakthroughs always come on the heels of the most epic failures. Hindsight is 20/20 and we can gain the most clarity by looking back on our flops, pivoting and strategically moving forwards.  Use that shitty logo, you can always change it down the line.

We must stop trading perfection for progress, perfection is an illusion that none of us will ever achieve and progress is a reward for those of us who allow ourselves the indulgence of failure. If we are not cringing at our earlier work, then we are simply not progressing in our craft. For some people, the predictability that comes with mediocracy is enough, but if you’re reading this, and if its resonating with you, you are probably not one of those people.  You probably feel in your soul that you are destined for more and you thirst for it like water. 

Ask yourself this question today.  What is the one thing you would like to do but you’re hesitating on because it’s not yet perfect.  Maybe its hitting publish on a blog post, maybe it’s reaching out to an influencer, launching a giveaway or starting a podcast (me!).  Now ask yourself, what is the worst thing that will happen if you do it?  Will you die?  Will other people die?  If the answer is no then you have the all clear for take off. 

Feel all the fear, self doubt and apprehension, wallow in it for a minute or two, and then go for it.  If you end up with pie on your face clean yourself up and be grateful for the free meal.   

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To thine own self be true ~ in order to stop trying to please everyone else, here’s the one question you need to ask yourself.

Years ago I ran an online vintage shop called onefortynine vintage, maybe you’ve even heard of it?  It grew quickly, scored some influencer/celeb clients and made me enough money to buy a modest house and stop living paycheck to paycheck.  My shop was born at a time when very few people were selling vintage online and so it became a big (or at least a medium sized) fish in a small sea.  But as more and more vintage shops opened around me, mine slowly dissolved into obscurity, and looking back now I can see exactly why.  I had tried to make my shop something for everyone else and that was my downfall.

When out picking, I would grab whatever I thought someone else would like. My collections would look like a rummage sale pile; leopard pants, gunne sax dress, 50s gown, silver lame’ shirt, 90s space boots, it was a crazy beautiful mess, and could have been amazing if that was actually my aesthetic, but it wasn’t.  My basement was filled with inventory that I would never even wear and my sales began to slow to a trickle.

I would post outfits to IG and immediately get unfollows.  It was a constant sinking feeling of what was I doing wrong? In fear, I stopped using ‘the gram’ altogether and missed out on some of the best years of organic growth.  Looking back its clear that the people who had followed me for my 50s dresses weren’t there for my 80s pantsuits, and people shopping for 90s athletic gear wanted no part of the boho pieces I would drop.  Rather than unapologetically just showing up as who I was and offering clothes that I loved regardless of the follows, I was constantly chasing my tail.  My brand had no identity and stood for nothing. 

Today, as consumers, we are blessed with so much choice.  (Almost) anything we want can be ours at the click of a button.  So naturally we’re becoming pickier about the brands we chose to buy from.  Not only do we want a clear aesthetic, we want our brands to stand for something.  This is why big name retailers seem to be loosing their footing while small fashion labels are rising up out of no where and becoming giants in their own right.

Can you imagine if a gluten free bakery chose to occasionally sell cakes made with conventional flour? Not only would they lose a whole lot of celiac customers, the people who eat wheat would probably not even go there to begin with.  They are at the bakery down the road specializing in chocolate, or LGBT baking, or cakes shaped like celebrity faces.  There is so much choice for the modern consumer that trying to be something to everyone will just make you nothing to no one.  The riches truly are in the niches. 

Now, I unapologetically stock my shop with lots of earth tones and neutrals, there is very rarely a print to be found, and I choose natural fabrics as much as possible.  I’ll often pass on great pieces if the fabric is bad because synthetic fabrics are terrible for the environment and being eco-friendly is something I stand for both as a consumer, and as a brand.

My growth has been slow but steady and completely authentic.  Many of my customers come back to order more and I’m building lasting relationships with those beautiful humans.  I completely refuse to play the follow/unfollow game as I can’t imagine a less authentic use of my time.  If people want to stay updated on my offerings, amazing, if not, buh-bye!  I now view every unfollow as a blessing, one less person in my space who doesn’t want to be there is a good thing and it helps me show up even more authentically for those who do.

I know my shop is not for everyone and I’m ok with that.  Its actually way less pressure on me and I loooove what I do because it is so authentically me. 

How about you? Have you ever struggled to grow or found your growth stalling? Do you sometimes feel overwhelmed by trying to capture too wide of an audience or are you trying to create a product with everyone in mind? Do you feel like you’re trying to do too many things so that you can provide an offering to everyone?  If you are struggling to niche down your own business I suggest first and foremost asking yourself this question:

Who are YOU as a person?

Deep down in the very fibers of your being, what makes you tick? Who is inside of that skin suit working the controls? A lot of people will tell you to design your ideal avatar (shes a mom, with three kids, and a parrot and she takes salsa lessons etc.) This can be a useful exercise for established entrepreneurs, but I think it can be too broad for someone just starting out or stalling out.  The most authentic way to design your avatar is to use yourself as a mood board.  You know yourself better than anyone, you can dig really deep and understand the way you think, the way you feel and the way you spend your hard earned cash.

Dig deep…

What turns you on and what turns you off?

What are your favorite colors?

What are the last 5 things you have bought for yourself?

What is your dream house and where?

What are your values, at your very core?

What are your hopes, dreams and goals?

How do you want to show up for the world?

What are your ultimate deal breakers?

What makes you smile?

Imagine yourself as your ideal customer and you will find the ability to be so empathic that it would be impossible not to build a brand that has an authentic voice.  Be true to yourself first and let the chips fall as they may.  Your brand may be small but it will be mighty.  You will serve the people you were designed to serve and you will be able to do so with such impact and authenticity that you will not easily be forgotten.

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