The Courage to Have (and Ask) Questions





“There are no stupid questions.”

We know this to be true. (At least, we’ve heard it enough to hope it’s true).

But what nobody talks about is: what does it mean if you don’t even know what question to ask?

Sometimes, in times of great conflict and confusion, I feel like a cartoon character: a great big question mark over my head. In this state of mind, I feel like sticking my head in the sand and throwing a little pity party.

When I’m in way over my head (as I now seem to be most of the time) things come up that are so perplexing that formulating a clarifying question (even a “stupid” one) seems hard.

A great example is an area of business that many entrepreneurs struggle with: Finance.

From the internal (bookkeeping and records) to the external (fundraising and pitching) there is a TON of new information to absorb. It is literally like another world, with another language — and I had no clue where to start.

Unlike making and selling the product (tangible, accessible — and fun), finances are not always intuitive and can often seem “not that important” in the scheme of a start-up. I remember saying things like, “Why stress out about tracking sales right now? We’re only selling a few thousand dollars worth of product a month — I can practically track it in my head!”

Once we felt the need to get our act together for tax time, I dutifully punched numbers into Quickbooks — then relied on our financial advisors and Accountant to process the information for me. When there wasn’t much feedback on our numbers, I was relieved — that meant our numbers were fine! No need to stress or investigate further…. Keep punching numbers.

The same on the legal end of things. After we formed our company and got a fat binder of documents from our lawyers, I didn’t think too deeply about what sort of company we were (Partnership, LLC, C-Corp… whatever!). I kept on sampling product at stores and doing all the “real” work on the front end.

Honestly, I thought that our accountants and lawyers would be like new Wild Friends team members — they would call out an alert if something wasn’t good, let me know if my numbers were wrong, tell me what to do and when to do it.

It turned out that’s not what accountants and lawyers are for — they are there to answer your questions, not question your methods or decisions.

I wasn’t asking enough questions.

I didn’t even know what questions to ask.

It took our company’s first outside fundraising round for me to look up and realize that I needed to really, actively, engage — to take responsibility for good bookkeeping, solid legal understanding, and excellent future projections.

After all, the future existence of our company depends on these things just as much as on a good product and growing sales. If we can’t prove our company’s worth to investors, we won’t get outside capital — and that’s when growth stops, even (especially) in the fastest-growing, most successful companies.

So, I had a fire lit under me! I really wanted to learn. But, I STILL didn’t have any real, specific questions — just that big question mark hanging over my head.

I started with basic self-education: I read this book, and this one (both highly recommended). I gained a greater understanding of finances and company formations! This was exciting.

Even better: With all this new information came TONS of new questions.

At first, this made me feel a little overwhelmed, but in hindsight, this is GREAT.

This is when advisors, accountants and lawyers really start to come in handy. They are fountains of information — once you know what to ask, the advice and information will come to you.

Usually this information will bring with it a whole new set of questions — but this is how learning happens.

Truth: it’s scary and hard to find and ask the right questions… but not nearly as scary and hard as it is to live with your head in the sand.


How to Throw an Entrepreneur Pity Party

1. First, think of a few frustrating things that have “happened” to you and/or your business over the past couple weeks (never take any ownership of these problems because then it will be harder to feel sufficient self-pity)

2. Fiddle around on the computer pretending to work and instead cycle through various food blogs (while really wallowing in self-pity… a hopeless attitude is helpful here)

3. When your friends ask what’s wrong, tell them as dramatically as possible about your “problems”. When they have reasonable and perfectly good solutions for you, roll your eyes and think about how they just don’t understand the struggles of being an entrepreneur…

Clearly, I’ve gotten pretty good at this.

Self-pity is a trap I fall into when I am feeling overwhelmed in the face of a challenge. 

I decided it’s officially time to take ownership of the areas of my business that I struggle with, rather than throwing a pity party. Stay tuned for progress.

My New To-Do List


A new lesson for me in keeping things simple: the basic To-Do List is my new favorite productivity tool. Oldest trick in the book, but it works incredibly well!

No separate categories, or fancy apps, or pre-scheduled phone alerts, just this notebook that my grandma gave me for Christmas (the congratulatory cover has also been great for my self-esteem).

I realize this isn’t groundbreaking in any way, but somehow giving myself the freedom to be “less organized” (keeping a haphazard, random list without a real “system”) has allowed me to focus my energy on completing tasks rather than categorizing them. I almost find the random order inspiring — changing focus throughout the day keeps me engaged.

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At the end of my work day, I quickly jot down all the items left to be completed on my current project, so in the morning it’s easy to pick right back up where I left off.

It’s also been a great way to jot down new tasks that come in via email without losing track of the bigger project I’m in the middle of. When previously I might have set off to complete the smaller “to-do” right away and gotten distracted from the bigger picture, now I just make a note and continue working.

Keeping my list constantly updated is also very personally satisfying (love checking the boxes!) and a fun way to keep track of what I am working on throughout the year. Hoping I will keep it going throughout 2014 — so far my productivity has increased in a very promising way.

Our (2nd Annual) Founders’ Dinner


As anyone familiar with Wild Friends might imagine, Erika and I spend a LOT of time together.

Not only is Erika my best friend, business partner, running buddy and (basically) adopted sister, but she is also my roommate. We’ve lived, worked, exercised, and socialized side-by-side pretty much non-stop for the past five years.  So… we know each other pretty darn well by now.

Lots of people compare business partnership to a sort of marriage — and they wouldn’t be too far off the money. It’s absolutely a committed, complex, relationship. Anyone who has ever started a business or worked on an extended project with one other person can understand the myriad of complications involved.

One of the questions Erika and I get asked most often is how we have remained best friends while also juggling these other shared roles.

It’s not easy. We’ve had our ups and downs. But, ultimately, what’s been the key to our success is the same thing that an old married couple might tell you: maintaining great communication.

It is so important that both Erika and I stay excited and passionate about the business — that our dreams for the company and our dreams for ourselves are expressed and aligned. When we forget the big picture, it’s all too easy to get lost in the day to day boredom of our separate tasks and phone calls. That’s when our little frustrations filter to the top, and (as our friends and families can attest) when our “old married couple” bickering rises in frequency.

This is why I love our new yearly tradition of a “Founders’ Dinner” (which we kicked off last year in style at Ox, here in Portland). Of course, we love any excuse to go out to a fancy dinner (that Meals and Entertainment section on our balance sheet was looking a little low anyways, right?), but above all, it’s a really good feeling to be out with my best friend, talking about the business we started together. Just like the good old days, when it was just the two of us and a couple food processors, and we could spend hours just chatting about our big hopes and dreams. No to-do lists or cash flow discussions or meeting agendas, just a great conversation.

This year for our 2nd Annual Founders’ Dinner, we headed down the delicious, carnivorous route yet again — this time to Laurelhurst Market. In between bites of amazing deviled eggs, sautéed collard greens, clams, steak and a glass (or two) of wine, we talked about all kinds of things (I’d be lying if I said we stuck completely to the realm of business… we are best friends too, after all!), but, most importantly, had a big-picture conversation about our company.

Wild Friends is going through some major transitions right now, and Erika and I are also making some big leaps personally as well. Taking the time to get on the same page, get excited for the year, reflect on how far we’ve come, and talk about next steps together is so fun — and it reminds me why we’re on this crazy adventure in the first place.

The Best I’ve Read This Year: Fiction


Freedom by Jonathan Franzen

This novel is nothing short of a masterpiece. I read this book with a friend (what we’re calling a “two-person book club”) and I am so glad I did — this is the kind of book you’ll want to discuss with everyone you meet. Featuring an intriguing cast of characters in a contemporary setting, incredibly and uniquely well-written,  and interwoven with current events and issues, Freedom is worthy of all the literary acclaim it has received. Read it, then call me to discuss… I will honestly never get tired of talking about this book!

Beautiful Ruins by Jess Walter

Another best-seller worth the hype, Beautiful Ruins is set along the Italian coast, not far from the Cinque Terre. Written back and forth across time zones and through multiple character’s perspecives, the book never loses momentum and kept me interested throughout. The writing style is light enough for a quick vacation read, but the zany characters and unpredictable plot line keep it interesting. Plus, it’s funny — an added perk that made me laugh out loud a few times.

The Boys in the Boat by Daniel James Brown

I suppose this book is technically non-fiction, but I already included it in this post soooooo it’s going to stay here. After all, this book was so well written, the characters so well imagined, that I felt wrapped up in a rich novel rather than a true story. This dramatic novel tells the story of the USA 1936 Olympic Rowing team — from the team member’s humble Depression era beginnings through the team’s incredible quest for a gold medal. An fascinating, historical page-turner.

A Storm of Swords (Game of Thrones Series) by George R. R. Martin

A commitment to reading the Song of Ice and Fire series is not for the weak of heart.  The six long and detailed novels (with a seventh forthcoming) take place in a fictional world with a history of thousands of years. Throughout the novels, a dynastic war throughout several prominent families rages.

I’m only through the third book (taking breaks between installations), but the series keeps getting more interesting. I highly recommend diving in — especially during these winter months that create the perfect setting for a nice long read.