Passion. You’ve really got to love what you do if you want to maintain it for the long haul. Especially in the beginning when you’re not making money and you’re almost “working” as a hobby. And, when you start to tumble or question, you’ve got to love it. When I began to start questioning my shopping services (and my concerns of contributing to overconsumption), I still knew I had a passion for the relationships of styling and what wardrobe can do as a tool of self-confidence.
Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing (Hanna Donnelly).
Hanna Donnelly, the owner of Hanna Lee Style, has been a stylist for over a decade and has worked on sets of TV commercials for Fortune 500 companies like Pepsi, Kraft, McDonald’s, and more. After seeing so much waste in the fashion industry she became an advocate for sustainable style (After all, she’s been a secondhand fan for years, wearing her grandma’s clothing for a decade). Now, Hanna is an online stylist helping women entrepreneurs look put together quickly with comfortable, stylish outfits so they can spend time where it matters.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
I began like most entrepreneurs, with passion and a dream. Frankly, when I first started, I simply loved shopping and how a wardrobe could be used as a tool to increase confidence. Working on my first website, I was doing before and after photos (they were comically bad looking back) but the photographer asked if I’d ever considered TV styling, which I didn’t even know was a job.
I said, “Sounds fun!” She knew someone who knew someone. Fast forward, I called and emailed that stylist, Leslie, for six months trying to get on a job. I even said I would work for free because I wanted to get my foot in the door. She kindly said, “No, we’ll get you paid.”
Long story short, I eventually got a job with her and stayed with styling TV commercial work for seven years while building my private client business, Hanna Lee Style.
Slowly but surely, I kept at it and here I am 13 years later!
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
A couple of things happened but as my business grew, I became increasingly troubled by the waste happening in the fashion world. I remember standing in Bloomingdales and there were racks and racks of clothing on sale. It was a jumbled mess and felt quite depressing.
I stood there, thinking, “Where will all of this end up?” That really got my wheels turning and led to further inquiry and my journey of sustainable fashion.
Coupled with an invitation from a client (now friend) of mine to a high-end hat luncheon at one of Chicago’s most elite private clubs. I’d given myself a 100 dollars outfit challenge, which ended up changing my shopping life forever and my foray into thrift / secondhand wardrobe.
Unknowingly, I’d been a fan of secondhand fashion for a decade- I’d already been wearing my grandma’s wardrobe but I had never gone thrift shopping before.
After that, I slowly introduced secondhand wardrobe to my clients and they loved it (affordable designer clothing and they didn’t “have to do the digging”). However, it still had limitations, especially sizing, which was so frustrating. So I still had to shop mainstream retail but I tried to shop small businesses as much as possible. Supporting small, women-owned businesses is a value of mine, so my collections of the wardrobe were curated mostly from small businesses, independent designers, secondhand, and a few retail basics.
Meanwhile, the other half of my business, a virtual outfitting service, Instantly Outfitted, was growing and I have clients across this country. It helps entrepreneurs know exactly what to wear for their branded photoshoots. It’s been fun using my TV styling knowledge and pairing it with a small business!
Lastly, a mid-pandemic hit and an experiential marketing company reached out to me looking for virtual styling events, and scared-but-excited, I jumped in full force.
That was life and business changing for so many reasons. First, I discovered I loved teaching online which meant I could serve more folks, and secondly, people really engaged, especially during the rapid-fire style Q & A. I was getting messages on social media (after my events) which is always inspiring.
I was hooked and knew I was finally “ready” to teach everything I’d learned over the past thirteen years as a personal stylist. So I launched my online styling course, Sustainable and Stylish, teaching folks how to build a wardrobe they’ll wear for years, better mix and match their current items and how to shop affordable sustainable options online.
I began selling it before I made it public.
In hindsight, everything seemed to unfold in exactly the right order.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
Natural born all the way! Plus my parents also always had entrepreneurial endeavors growing up so that certainly helped the entrepreneurial nudge. We were encouraged to do what we loved from a young age. I launched my business right after college in 2008, which as you can imagine was pretty difficult in a recession.
And, in full transparency, my parents were still helping me those first few years after I graduated so I was certainly privileged in that way.
Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?
My grandma Jean’s style and love for wardrobe inspired my entire career.
Ultimately, her love for wardrobe and how she showed up (despite the occasion or setting) really inspired me. For example, there was a local hot dog restaurant we used to frequent on our visits, and she still wore her sharp blazer, trousers, perfectly coiffed wig, and red lipstick.
Something about that really inspired me- not dressing for the occasion or setting, but dressing for one’s self. I inherited her entire wardrobe when she died- that’s been quite the journey!
Secondly, my brother, Peter. He helped me build my first few websites and holy patience. He deserves a medal. Those websites definitely made me look more professional than I was at the time. Kind of like wearing a put-together outfit, appearance makes a difference (whether we like it or not).
What do you think makes your company stand out? Can you share a story?
I’ve always been a little too practical (I borrowed my wedding dress and had a second party dress that was a 200 dollars bridesmaids dress) and perhaps even too honest but I think that’s what made me successful. There was a potential client that was showing me her latest haul, asking for my opinion and I remember telling her to return it all. She already had the pieces (just in different versions).
She didn’t hire me after that session.
That’s happened a few times. I’m definitely not the stylist for you if you want to know trends or buy for the sake of buying. That’s when my sustainable style kicks in. I will not encourage you to purchase things for the sake of purchasing, we all have plenty of stuff.
I’m also incredibly honest. If I don’t think my services will benefit or serve you, I’m going to tell you so. I’ve had many (potential) clients surprised by my candor but morally I can’t encourage people to buy if there’s no need.
At the end of the day, I don’t actually care about wardrobe but I DO care if it’s stopping you from living the life you want. If you’re not taking risks, or dating, or going for that presentation because you’re scared of what to wear?
That’s when I care. Hire a stylist.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Perseverance, knowing and honoring your values, and creating strong relationships.
I want to yell from the rooftops to so many young people that reach out to me (or anyone) for internships. They email once and that’s it. ONCE. It drives me mad. We all get flooded with emails, it’s so important to follow up. As an entrepreneur, perseverance is key. As I shared earlier, I literally followed up with that TV stylist for 6 months before she brought me on a job. And, I offered to work for free. I just wanted to get my foot in the door.
And, rejection happens. Just recently I was following up with a potential client and she curtly responded “take me off your mailing list” — I kindly responded that it was actually me writing her, not a mass email list, to see if she still needed help (she didn’t).
Those rejections still sting (even 13 years later) but it’s part of the business.
If you never ask or follow up, you’ll never know. I cannot emphasize enough how important perseverance is. I think it’s essential in entrepreneurship.
Knowing and honoring your values
I’ve been fortunate to have experienced a lot of personal growth and development work, from a very young age so I knew my values young and kept growing that muscle. But I’ve also developed new ones along the way, like caring for the planet. In the past five years, it’s become increasingly important to me, but it wasn’t always that way. I’ve definitely become more aware.
When you know your values and take aligned action- that is a success. That’s why sustainable fashion has become so important to me.
As I shared earlier, I don’t actually care what you wear. I DO care if the wardrobe is stopping you from living the life you want.
I care deeply about my clients and the lives they lead. Eventually, I’m more coach than a personal stylist. (So much so that a long-time client told me, “I don’t want to offend you but I think you should move on from wardrobe and consider coaching). I had more or less become her life coach and we had a great relationship.
Additionally, I care about the small businesses I support. Supporting their passion and businesses is a huge value of mine. I love supporting folks to fulfill their dream lives.
Life is so much richer with relationships.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Honestly? No. If anything, I wish I had followed most advice sooner. I can be stubborn.
Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?
Find an outside eye or a coach with similar values so you can have those honest conversations- there is nothing greater to me.
Unfortunately, I think burnout and overwhelm happens. It’s a part of life, the ebb, and flow. How you react is the part that makes the difference. Find what works for you.
If you’re stuck and keep feeling the overwhelm consistently? Keep exploring until you find what does work for you.
I’m a big fan of crying when needed, getting fresh air, journaling, laughter with friends, and conversations with folks I love.
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Be in relationships with folks outside of your industry. You never know what conversation will spark trust, credibility, and authority.
And put yourself out there (which isn’t always easy for us introverts) but ultimately it’s a great way to build CTA.
Can you help articulate why doing that is essential today?
When you have more relationships in your life and keep sharing your message, eventually people will know you for that message and start sharing. They’ll be able to think of you easily if the opportunity fits.
For example, a neighbor I had decades ago (almost 30 to be exact) just recently DM’d me via Instagram and sent me a sustainability article about an up-and-coming fashion line.
A few things that stood out to me about that: a) I had no idea she “followed” me (you never know who will see your message) and b) my message was standing out to folks that I care about something sustainable and they were recognizing this.
Days later a friend sent me information about a local eye doctor who was collecting plastic contact lens packs to recycle.
When you believe and share your message consistently, the right people will find you.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Doing everything yourself, being all the things. (Been there, done that).
As a recovering perfectionist/control freak, it’s so easy as an entrepreneur to do it all but it’s not sustainable for the long term and it’s certainly not helpful, especially if you want to scale your business.
This is a work in progress for me. Mostly because I lack patience.
Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?
I think the hardest part about being an entrepreneur is that YOU are both your biggest fan and biggest critic. Finding the balance of the two is challenging. So no matter how successful something is or seems, you always think it could’ve been better.
There’s also seemingly a never-ending list of things to do, versus at a “regular job.” Entrepreneurship isn’t like that. It never feels “done.”
Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.
After my first virtual styling event! I was getting messages about how fun and different it was and they loved the tricks and tips. That was a joyous moment for me. Working from home, virtually, reaching folks all around the country, doing what I love coupled with their enthusiasm? Entrepreneurship gold.
Another high moment was when I worked with a younger gal in college, she was interning for a law firm and needed to look the part. Her uncle hired me. I discounted my service fee (which I’m not one to do) but my gut told me to. In addition, he’d given me about less than half of the (wardrobe) budget I was used to. I curated such a strong capsule of clothing for her and she LOVED it. Her joy and confidence in the dressing room were contagious, I can’t even articulate how happy she was.
She emailed me years later and told me that she still gets compliments about that wardrobe. That was one of my favorite transformation experiences.
Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.
When I first started. Not only did I start a business in 2008, a serious recession, but I started it around shopping. Holy naive (but my mom likes to say it’s one of the reasons I’ve been so successful, that my naivete helped me).
Those first few years were so frustrating, hard, and honestly? Lonely. I also had zero clues about what I was doing. While I’m not really a regret type of person, I do wish I had interned for a personal stylist in some capacity.
If nothing moves you lose momentum and I was losing momentum. I was feeling pretty lost so I saw a therapist and he said something to the effect of “I think you should get a job” and I remember being so heartbroken but also thinking, “Yeah I probably should.”
Based on your experience can you tell us what you did to bounce back?
I needed cash and flexibility so I could continue to pursue my entrepreneurial journey so I found a nannying job that allowed me both.Then in 2012, I took an online course for entrepreneurs that really, at the time, got me excited again, especially around finding a niche and marketing.
So getting a flexible job and finding a like-minded community absolutely got me on the way again.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.
You’ve really got to love what you do if you want to maintain it for the long haul. Especially in the beginning when you’re not making money and you’re almost “working” as a hobby. And, when you start to tumble or question, you’ve got to love it. When I began to start questioning my shopping services (and my concerns of contributing to overconsumption), I still knew I had a passion for the relationships of styling and what wardrobe can do as a tool of self-confidence.
You keep going until you find what works.
Luckily I found a sustainable style and secondhand fashion, which gave me hope for the fashion industry and my own personal morals and values. That I could continue doing what I love and still honor my values.
2. There’s enough for all of us
Sharing the love, in every sense of the word. I happily (still) recommend other stylists if I’m not the right fit for a client.
I remember in my TV days when I recommended another stylist and the (lead) stylist on the job commented how confident I must be to recommend someone else. I stood there a little perplexed and thought to myself “How selfish would it be to NOT recommend someone else?” I’d want someone to do that for me if they thought I was a good fit.
I don’t believe in the “there’s not enough” mentality. It serves no one.
3. Solution-oriented optimism
Optimism is lovely but solution-oriented optimism is when you can face something with excitement and a solution. The pandemic nearly cut my business in half and while I could have freaked out (and I did for a few days), I experimented with new ideas and now am well on my way to even greater success, spiritually and financially.
Now I’m able to teach virtually with my online course, Sustainable and Stylish, with folks all over the world. I feel like I hit the entrepreneurial jackpot.
And, there will always be “fails.” Mid pandemic I thought it would be smart to get my wholesale license so I could gift boxes of curated, beautiful things. It was a total bust. But am I glad I tried it? Absolutely.
I remember complaining to my mom once about not being where I wanted to be financially in business and she said, “Hanna. You’re richest in everything most important to you.”
She meant relationships.
And she was right. I’ll never forget that and how much it meant to me (still means to me).
I think it’s easy to lose sight of what’s most important, especially as an entrepreneur because you’re always challenging yourself to grow. But I truly believe there’s nothing greater than knowing what’s most important to you and then practicing gratitude around said importance.
5. Relationships & Community
There’s nothing greater to me. Friends, partners, children, your support system, you name it, and relationships will help you carry yourself through the best and the worst of times. In 2019, I joined Megan Flatt’s, Let’s Collective, and that felt life-changing for me, to meet and be in conversation with like-minded women that wanted to grow their businesses but also cared about social justice and bigger-picture views.
I’ve been fortunate to have been introduced to the world of coaching before it was a “thing.” My parents were really progressive that way. I had a life coach for practically my entire teens into young adulthood so that taught me that outside support was not only “okay” but encouraged.
I am so grateful for that.
We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?
I think of the movie Finding Dory. At some point I think she repeats to herself, “Just keep swimming, just keep swimming.”
Entrepreneurship is totally like that. You’ve got to just keep swimming. Do one thing a day that moves you forward towards your goal.
One action a day can turn into multiple actions, you’ve got to just start and keep going.
Traits of resilient people:
- Thinking outside the box
- Experimenting (there are no failures, just lessons)
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
As I shared previously, I was so privileged to grow up with coaching as a norm and be in the world of personal growth and development so that really did shape a lot of my thoughts around integrity and authenticity at a really young age.
Those words were in my lexicon and everyday language before they became buzz words.
I think of my time at boarding school, 16 years old, on the east coast and I was not living my best life (excessive drinking and a bad relationship).
A teacher at the time, Rocky, encouraged me to check out Outward Bound.
(In hindsight I wish I remember more of this conversation but nonetheless he told me to check it out and I did..)
It was a wilderness backpacking trip and one of the instructors was reading this poem and I just *knew* I wasn’t going to go back to boarding school. I no longer wanted to continue the life I was previously living.
That choice felt both powerful and sad. I had some really good female relationships that I knew I’d greatly miss.
I moved home with my parents to finish my last two years of high school, starting to gain my parent’s trust back and my own. I met my (now husband) at that high school and we’re currently back in the area raising our son, close to family.
Life is funny.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
Yes, definitely. I always try to find the good. Have I had challenges? Of course. There’s not one human being that doesn’t experience challenges, sadness or have setbacks.
However, I do think it helps to try and stay positive.
And with that said, I know I am privileged as a white, able-bodied woman. We have a long way to go with inequities and a lot of work to do as a human collective.
Ultimately I want to leave this earth a better and kinder place. I work towards that daily in the choices I make (from where I shop to the friend I am).
Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.
Truthfully? Sometimes I wonder if my clients hire me for wardrobe help or they just keep having me come back because they like my optimism. I like to think it’s certainly both. I shared earlier when a long-term client of mine basically told me to move on from styling and to start coaching (mostly because we’d completed our wardrobe relationship and she was all set but she loved my coaching!)
Most of my styling relationships are so much greater than wardrobe.
I also like to think it’s a trickle-down effect on your team, I know my folks feel excited when I am. That matters.
Life is so much greater when we can attack it with positivity. And, as a highly sensitive person, this can be challenging with our world events, but I try to remind myself that my positivity is greater to the world than my sadness.
Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?
Going back to my mom here when she reminded me that “You’re richest in everything you care most about.” That reminded me that I have everything I need. Everything afterward is just a bonus.
Find out what’s most important to you, make it happen and then live like everything else is just a bonus.
How can our readers further follow you online?
Folks can find me www.hannalestyle.com and join my newsletter if they like easy style tips, comfortable and stylish outfit ideas, and affordable sustainable clothing,
And, I’m @hannaleestyle on all social media. I currently hang out the most on Instagram but that could change (part of the entrepreneur journey- it can all change quickly!)
This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!