Congrats, m'dear!

Smitten you've tossed your fascinator into the ring for Chief of Staff and can't wait to hear more ...

Before we move forward, I want to give you another pass at what this position is like from my perspective. For my last two CofS's we've realized in hindsight the position wasn't right for them {fabulous as they are} so we've worked to hone in on why this job is unique.

Please consider afresh if you're truly the disposition for this position, and if not no worries! No need to reply and "remove your name", just don't submit for the second round and I'll know you decided there's a more perfect pairing for you out there.


The Calendar

One thing we've realized was unclear in the past is that a small business goes through ebbs and flows with launches. While we might set that you're usually working Monday to Thursday from 11-3 ... when the next round of Style & Styleability comes around that schedule could go out the window.

Suddenly a website link isn't working. We get an email that points out an obvious FAQ we didn't address. Our mailing list provider crashes. There's more customer service emails than can be answered within your set hours.

And those launches have to take priority for the team as a whole. They can't be the same week you're moving or on vacation. They're our capstones -- some bigger launches, some smaller -- but I need someone I can text at 11pm the night before the doors open without feeling guilty.

However, I desire those times to be rare. We're transitioning into a rhythm of being more focused on a handful of big launches a year, a handful of small ones, and intentional seasons built in between where we're just doing organization/maintenance/prep/rest.

I talk extensively in my book about "seasons" and that's how I'm crafting my life. I want to be able to apartment swap in Paris for a month, where I'm only working part-time on that prep/maintenance side. And I know there'll be another month where I turn down lots of social time with friends because we're launching something big.

I'm not there yet. But I see these three years of hustle coming to a new place of balance in 2015.

If consistency throughout your year is what keeps you happy, you won't be happy hanging with moi. If a high/low rhythm sounds and feels appealing to, you'll love this job. 


The Nanny's Nanny

Another point of clarification is that a mama with kiddos under school age, can't kill it as a CofS if she's moonlighting as her own nanny.

If you have a babysitter for your little one during your working hours, fab! But if you have visions of multitasking Dean St and your little one at the same time, we've found that fevers and toddler meltdowns mean you're unavailable for a conference call or a deadline.


The Therapist

Entrepreneurship is an emotional journey, love. It's something I'm often preaching to my business mentoring clients because I don't think it's addressed in the online world enough.

I love what I do. But for the last three years there hasn't been an off-switch. So I'm often tired, which means an email from an unhappy client sends me into tears. Or when that email comes in it feels like such a personal attack, because my business is so personal, and I've been working so hard, that my anger bubbles over at how someone could not realize that.

There's lots of ways in which I'm happy to say I'm not a perfectionist. Those details don't stress me out too much. I got to where I am because I'm willing to ship on "good enough" when I need to.

Other times life is grand, but I need a sounding board. I need to process aloud whether or not to kill that next program, raise the price, say no to the opportunity. I can easily have hour long conversations with my CofS because the rest of my day is spent in solitude, and conversation gets my creative and problem solving juices flowing.

I've had a freelancer who had anxiety attacks and couldn't emotionally handle my nerves after an all-nighter when we were relaunching the website. I've had a right-hand girl who was kind of exasperated at long phone calls. So I want to prep you, that there are moments when this is like being a therapist -- listening, supporting, asking good Qs, giving advice, handing out the virtual tissues.


In Her Words

Here's what my current CofS shared as we were musing via email this week about why she'd realized this position wasn't right for her:

" ... the emotional aspect of entrepreneurship and the fluctuating hours.  I didn't expect that.  Maybe I should have, but I'm just so used to working in more "normal jobs," I'm used to compartmentalizing and regularity.  Plus I think for me, with my husband coming and going in the military, I just have other emotional strains. I didn't expect work to be one, and I did try to compartmentalize.  But it's not possible with entrepreneurship.  It was just too much for me.  It wore on me and drained me.  I'm a pretty laid back person, and I don't always take stress, anxiety, and high-paced things well.  So I guess there is some personality-type to be considered.

The fluctuating hours -- I underestimated that, and it was hard because a good portion of the launch fell when my husband was home on leave.  And to be working instead of being with him, just broke my heart. 

... I'm just not cut out to be an entrepreneurial chief of staff. You are incredibly unique and have some rare gifts.  I'm not buttering you up cause I'm leaving.  It's really true.  I think you need someone to balance you out in ways, but you need someone a lot like you in ways, too.  Like you talk about in your book, you were just born to be an entrepreneur.  You have the gifts, it comes naturally.  I think you need someone who has that as well, who can keep pace with you, invest emotionally, and put their heart in it.  I figured out that I can't do that. And you will be much better off in the long run with someone who can.  The way an entrepreneurial brain and business works is like getting caught up in this awesome, beautiful, stylish tornado.  It's exciting and fast-paced and so many things are happening and there are high high's and low low's and it's a scary ride but it's such a rush and sure can be fun.  I can't do that, I've learned.  That's just not me and I'm gonna be left in the dust."


And So We Continue To ...

Round Two

Are you still with me? Like I said, if you've realized you aren't the temperament for this type of adventure, no worries! No need to let me know you're withdrawing your name {thanks in advance for keeping my inbox lean!} simply don't send in your next round application.

If you are still with me though and thinking this sounds right up your ally, here's what I'd love for you to share with me next:


1. What are your Core Desired Feelings?

If you're unfamiliar, watch this video. This concept has been HUGE for me to explain why my life and career makes me happy, why I love what I love and loathe what I loathe.

And, how do you see your CDFs coming through in this job? Because that's what I want: you lit up, fulfilled, in your sweet spot, feeling how you want to feel. As often as possible. And this will be illuminating for me to understand how I can be someone in your life who supports you in feeling how you want to feel.


2. Affiliates

This September we'll be doing our first large affiliate push for Style & Styleability.

This is your baby. What do you do?

  • What do we send them for an initial introduction? Email, PDF, link to a page on the website? Write out {taking liberties in assuming any details you don't know like commission percentage, etc} what you'd send them, in your voice, signed by you. Give it to me in final draft form for my sign-off to hit send.
  • What platform do we use to track their opt-ins and sales?
  • Who are 10 entrepreneurs or bloggers you think I may not know and should reach out to as affiliates? What would be the hook for them, why would S&S be right for their audience, selling well for them and bringing us ideal clients?


3. Traffic

This summer I'm focusing on list building, something that has largely ended up on the backburner for my first three years.

  • Rank for me from 1-5 {1 being top priority} what you think we should focus on to drive traffic and why.
  • And then how -- how are we going to be smart on that platform/vertical and how will we stand out or do it well?
  • And who -- are you overseeing #2? Do we delegate #4 largely to an intern? Seek out a freelancer who's got mad skills in that area? Is it mostly something I'm taking the lead on because only I can really speak to it?
  • On the areas that are you, write out for me sample pitches/copy/text for that platform/vertical. If you're running with it, give me final copy in the Dean St voice that I can sign-off with to publish.


4. Video Love

To get to know you better I'd love you to film a two minute video. Nothing fancy, just pop open your computer cam. And talk to me about the growth of Dean Street Society.

I know you don't know my business plan, what I've tried and hasn't worked, why I've decided not to focus on X or Y, etc etc. But just give me your ideas. How do you see us growing in the next 1-3 years and how can you help in that?

In 2013 I've made Dean St a steady $100K revenue business. But to support a small full-time team, we need to grow to $300K revenue in 2015. Don't panic, I know behind the curtain this is feasible. {wink} But I want your ideas.

And again, just the two minute version to give me a taste.


How to Submit

Please hit reply on your original email application by Thursday at noon EST. That way your entire application will remain in one thread.

I'll dive into them as soon as they hit my inbox with the goal of sending out third round steps on Friday. 


P.S. The Timeline

For you to know where my head is at, my current CofS's last day is a week from Wednesday. In a perfect world, it would be great to have her available to do some training with her replacement early next week. But, I'm more concerned with making a wise decision on the right person than that rushing to a deadline. And if we need to bring her in later for a day or two of training, we'll do that.

However, the next Style & Styleability launch is coming in September, and there's a lot that needs to happen asap. So if you were one of those gals who said you'd need to give notice at your current job {which I totally respect!} let me know how realistic working part-time/nights/weekends and/or taking a sick/vacation day to moonlight with Dean St is while you transition out of your current position.

I've got various options rolling around in my head -- bringing on my past Project Manager to fill in the gap while I wait for the right gal to be free, hiring two gals at part-time who have different skill sets, etc. But touch base with me again on timeline knowing that honestly, losing my CofS right now is a huge blow to the momentum of what was a well-laid out summer, and I'm motivated to get us back on track as soon as possible so potentials for this September launch aren't squandered to a month of transition and treading water.


I remain so honored at your desire to be a part of Dean Street Society and can't wait to hear more from you ...