Ask An Expert: Taking A Risk & Following Your Passion

Hi!  Welcome to Finding Silver Linings!  This post is the first in a new series called “Ask An Expert.”  I will be interviewing experts in widely different fields.  I hope this series brings value to your life by either inspiring or entertaining.

Our first interview is with Jamie Lewis, Wall Street hedge funder, founder of JLEW Bags and boxer.  Her story has inspired me because she followed her passion and is unapologetic about forging her own path.

Tell me how you ended up following your passion (how did it start?)

The simple answer is there’s something I wanted and after looking and looking and not being able to find it I decided to make my own. Then all of a sudden I’d gone back to school at nights then quit my full time job and was managing a supply chain, overseeing manufacturing, selling direct to consumer and wholesale, hopping from pop up to trade show all while trying to build a brand, create a voice and community and get more stinkin’ Instagram followers . . . because everyone seems to judge a business based on the ‘gram which is the absolute case study for fakin’ it ’til ya make it . . . which, if you know me, makes my skin crawl. The more authentic, raw and real, the better in my mind. But that’s not very commercial, as I learned the hard way.

I still look back at the last two years in awe. It feels like it just happened out of nowhere, overnight and then I look back at the day to day grind and boy was it a grind. Someone gave me this advice when I was dragging on the struggle bus . . . don’t look forward thinking about how far you’ve yet to go; pause and reflect on how far you’ve come. I think that’s fantastic advice for entrepreneurs. I don’t know anyone who’s become an overnight success but I know an awful lot of people who grinded it out day after day, week after week, year after year . . . and ten years later they’re dubbed the overnight success because they finally hit critical mass/scale.

The longer story can be found here: http://jlewbags.com/team/

What have you become better at saying no to (distractions, invitations, etc.)? What new realizations and/or approaches helped? Any other tips?

I’m horrible at saying no, always seizing whatever opportunity or invitation comes my way. Honestly I forced myself to get 8 hours of sleep a night and work out at least once a day as an entrepreneur . . . prioritizing these two “must dos” forced me to say no in other areas like spending excess amounts of time with friends or at events . . . I’d ask myself is it really going to benefit me enough to sacrifice the time away from work and if so how?

Maybe the better question to ask is what did you learn to ask for? I think that’s a skill women need to practice . . . guys have NO PROBLEM asking for help yet women seem to think we need to keep our heads down and prove we can do it all. But why? All that does is facilitate burnout. Get help from others so you achieve your goals sooner and free up more time to spend with the girls . . .

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

I gave the commencement speech at my high school graduation and cited this advice/quote: “Probably the most valuable result of all education is the ability to do the thing that you have to do, when it ought to be done, whether you like it or not.” – by J. Thomas Huxley

Today I bark “suck it up buttercup” to myself, but it’s just another way of saying the same thing. Especially early in your career, take advantage of everything that comes your way. You’ll never have the same ability to learn or energy again like you do in those critical, formative years. Maximize the use of that time. Work hard. Play hard. Think of the long term and you might have an easier time making sacrifices . . . including saving money, working instead of making every friend outing, etc. Trust your boss – often they won’t have time to explain why they’re asking you to do something you might find inconvenient . . . but if you do it and become someone he/she can rely upon in critical moments, you’ll find so many more opportunities will open up for you. Every single thing you’re asked to do should be seen as a challenge, something to master . . . even making copies, coffee, answering phones . . . your attitude will be positive and your boss will want to have you around more often which is KEY . . . because that allows an opportunity for you to learn, which should be your number one goal right out of college. Before you can run you have to learn to walk . . . and while your boss might not be as tech-savvy as you, there are so many other skills and insights you can glean, but might not be obvious to you . . . be patient, have an open mind, a positive disposition and can-do attitude and you too will be surprised looking back after a year how far you will have come.

How has a failure, or apparent failure, set you up for later success?Do you have a “favorite failure” of yours?

Ha. I got cut from the cheer leading squad and ended up becoming student body president instead and that probably propelled me further on a path of wanting to achieve and act independently rather than fit into a clique . . . I didn’t get an offer to go to Goldman Sachs out of college and have been unemployed at various points in my finance career, but every time I landed something better that helped me learn and grow. The resilience that built from feeling so low and recovering, bouncing back even stronger really proved invaluable when charging ahead as an entrepreneur when no one believed in my vision but me and a select other few. An old boss wrote in a pitch book once “it’s always darkest before the dawn” – at the time I didn’t really think through what it meant and just thought he was being dramatic. I think about that truism again and again to give me perspective. It’s true!

What is your #1 advice for someone wanting to start something on their own?

Don’t overthink it. Just do it. Really.

When you feel overwhelmed or unfocused, or have lost your focus temporarily, what do you do? (If helpful: What questions do you ask yourself?)

I’m lucky enough to have some amazing friends and family who can always make me laugh and give me perspective. They’re the best support I could wish for and leaned on them whenever the going got tough.

That or the boxing gym. Punching really is a great stress reliever.

How do you think following your passion AS A WOMAN changes things?  Is it more difficult or in some ways easier?  Why?

I think we should host a live Q&A on this topic if you really want to dig in, as I have SO MUCH to say on this topic.  I have very strong feelings about this subject.  I’m so happy progress seems to be being made but am terrified that some might take it so far that it drags us further back . . . like one step forward and maybe five steps back, truly.  I’ve always been the only or one of only a few women in the room in college as an economics major then for the next twenty years working on Wall Street and I loved every minute of it.  I love women and I love men and I believe they’re different.  I will tell you that I saw a lot of female-founded VC funds popping up trying to invest in women-owned businesses, which is great.  I’ll also say that had I gone out and raised a VC round I would have wanted the best investors in invest in me, male or female and I never would have felt comfortable being granted anything “just because I’m a woman.”   I’m seeing a lot of “we need a woman” hiring and this feels very reactionary and haphazard . . . particularly at a time when I’m hearing industry veterans refer to all female sports as a whole as “an emerging sport.”

Would you guys be interested in a live chat maybe on Instagram on this topic?  Let me know!!