Small things that make me happy at work

I like to think and write about being happy at work. Call me an idealist, but I think we should all strive to get paid to do what we like — at least some of the time.

I organized a panel recently where we talked about turning our passions into careers. I invited three pretty incredible women to be on the panel and spent the entire night feeling damn lucky to be in their company: Leah Cramer, the founder of Craftster.org, one of the most popular online crafting communities (which she successful sold last year), Laura Zigman, a close friend of mine who is too modest to talk about the fact that her first book, Animal Husbandry, became a national best-seller, had a movie made out of it, and is widely considered to be the original chick-lit novel, and Christine Koh, the uber-sharp and fashionable brain scientist turned graphic designer and founder of Bostonmamas.com.

During the panel, Leah said something that I found incredibly insightful: “I grew up believing that it’s somehow wrong to get paid to do what you really love, that there was such thing as work, which you did for money, and then other things, like hobbies and interests, which made you happy.”

I never quite articulated this in my own mind, but I’m fairly certain I grew up believing the same. It made some sense in the Communist Russia, but it makes little sense in a country where, terrible economic times aside, we all get a shot to do what we like/love/are interested in/learn a lot from and get paid (something) for it.

In my conquest for being happy at work, one thing I sometimes forget to do is to be happy about the little things that make up my workdays. You know, to sweat the small good stuff. Things like:

• Having my daughter and my husband and my dad come to visit me at our quirky and warm Daily Grommet offices today. The office will feel that much warmer from now on:)
• Reading this too-kind of a post from the founder of Daily Grommet about my joining the team there.
• Being able to work on a flexible schedule, which means that I can pick up my daughter from school on some days and work late into the night to catch up.

These small things add up. Think of some of your own, I highly recommend it.

Fighting my inner perfectionist

No, you’re not wrong — I really have not updated this blog in over a year. I could bore you with lots of explanations, but they really are quite expected and boring: too much work, a lot of other writing, and choosing to spend whatever few spare moments I had with my family.

It’s the new year and I’m a total sucker for fresh beginnings, so after I finished filling in my 2009 planner with birthdays, anniversaries and other dates to remember, made a list of good things I did and learned this past year, I decided to go through my bookmarks. And there it was, my hardly developed and left completely neglected Learning Optimism blog. My first instinct was to just delete it, get rid of it. Not because I don’t want to have an outlet to write about all things blogging-entrepreneur-social media-start-up life-related, but because the inner perfectionist in me would NEVER be seen with a blog that hasn’t bee updated in a year.

But I’m going to put my inner perfectionist in hiatus just long enough to write this post and keep this blog. Because I love blogging. Because I want to keep track of the endless changes and learnings and professional roller-coasters in my life. And because in my not-so-humble opinion this is a damn good name for a blog.

So here’s to a year filled with imperfections (and hopefully less pauses between blog posts).

The rockin’ entrepreneur women the venture world is missing out on

One of the most unexpected benefits of starting my own company has been the chance to meet and form virtual friendships with some incredible, smart, inspiring, and gutsy women entrepreneurs. When I started my career in venture capital I thought that I would find many women entrepreneurs to back. Then the dark reality hit and I found out that there were not that many women entrepreneurs knocking on our firm’s door to look for funding. For the record, we did have 5 companies in our portfolio with women CEOs, but 4 out of 5 were brought in later and were not founders.

But since leaving venture and striking out on my own I’ve met some pretty awesome women entrepreneurs who are serious about their businesses but also serious about their lives and having more in them than just their business. Many are also moms and they are building their companies in ways that would make any venture capitalist cringe — they are working from their home offices, they (like I) take off in the middle of the day to pick up their kids from daycare or school or play with them outside, and their workday is as far removed from the traditional 8-6pm schedule as possible. Meeting these women has been an amazing experience and for the first time in my career I am developing a professional network that includes women I actually like and respect and want to interact with. They are supportive, they are not catty or bitchy or whatever the stereotype suggests — which is true too often — about women interacting with each other.

These women are running and starting different types of companies but they share a few things in common:

• Many have left successful corporate or more traditional careers to become entrepreneurs
• They see entrepreneurship as a way to gain more flexibility and a better ‘balance’ between work and family
• They are choosing to finance their businesses without taking venture funding, at least in the early stages, and they are incredibly ingenious about finding ways to fund their operations (bartering services/marketing with other women-owned firms has come up more than once)

I’m gaining new perspective about why there might not be as many women entrepreneurs seeking venture funding out there. I still maintain that those who do want it should have more access to it and one of the reasons they don’t is because there are so few women in venture capital. (To deny that it’s easier and more natural for women to network with women and for men to network with men would be silly.) But as I meet more and more women who are serious about building successful businesses but don’t want to do it with venture funding, at a venture-backed company pace, I am starting to think that one of the reasons more women don’t get venture capital is because they don’t want to.

So that you get to meet them as well, here are some of these rockin’ women entrepreneurs I’ve been lucky to meet recently (most virtually) — go give them a shout out!

Penelope Trunk

Aruni Gunasegaram

Naomi Dunford 

Wendy Piersall 

Aliza Freud 

Being an entrepreneur means learning how to know when you’re wrong and doing it quickly

When people ask me why we didn’t take venture capital to fund Work It, Mom! I give two reasons, both very different:

1. Part of my motivation to leave a career in venture capital was to see my daughter for more than 20 minutes a day and have some semblance of a life. I’ve invested in venture-backed companies and I think I have a sense of what it’s like to run one. At this point in my life, it’s not what I want to be doing.

2. I launched Work It, Mom! because I believe that the 30 million working moms in the US need an online community and resource dedicated just to them. But I don’t know if this means that we can actually turn this into a business. Do working moms have enough time to spend online and be involved in a community? Can our niche audience be big enough to attract solid advertising revenue? We don’t have answers to these questions and we can’t have answers until we run with this for a while and figure out if the business plan works. I don’t want to spend venture money chasing the wrong plan–a million dollars spent on marketing the wrong product is a waste of money.

I’ve gotten a lot of compliments for reason #2. People tell me that it’s “very sober and responsible thinking” and that they are impressed that someone with venture capital connections chooses to bootstrap the company and face the many difficulties that come with that choice (not nearly enough resources, no marketing budget, huge personal financial pressure, you know what they are.) But to me it’s the most obvious one.

And I was glad to read this post by Fred Wilson talking about failures and successes in his portfolio. What he has observed is that 2/3 of the companies in his various portfolios have partially or completely transformed their business plans in their course of their life and most of the successful ones did. Being a successful entrepreneur does not mean having the greatest idea ever that gains traction as soon as you launch it (which would be nice, by the way.) It means trying different directions and figuring out quickly which one is the winning one, without spending tons of capital in the process.

I find this perspective helpful, and the fact that it’s based on data reassuring. I don’t know if Work It, Mom! can be a huge business success–it’s so young and it’s so early to make predictions–but I gain some comfort in knowing that by bootstrapping it while we figure out IF our business plan can be successful we’re doing what has helped some other successful companies become such.

Having your own business means being scared every single day

Since we just moved I’ve been meeting new people all the time. Inevitably the “What do you do?” question comes up to which I answer that I started my own company recently. The responses usually take the form of “Wow, that’s exciting!” and I nod and smile politely in agreement.

But let me be honest here. What I’ve learned from my six-month stint as a full-time, no security blanket entrepreneur is that mostly, it’s freakin’ scary. Yes, I said scary. It IS exciting, and wonderful, and amazing, and gutsy, and interesting, and fulfilling, and many other adjectives, but every single day, it’s scary. And it’s the kind of scary that I’ve not experienced before–a deeply ingrained, constant state of scary vs. something that just comes and goes. To be perfectly clear–or too honest, as a friend who has been reading this blog recently said to me–here are some things I am scared of:

• I am scared of failure. I am really really scared of failure. Work It, Mom! is something I’ve created and I’ve gone out into the world saying “Hey, world! We need a community for working moms called Work It, Mom! and I am going to create it and make it into a real business.” The odds of success are tiny, the fear of failure is huge.

• I am scared of what my friends, family, and professional colleagues/contacts will think of me if I can’t pull this off. I wish more people talked about this openly. No, I am not doing this for anyone else, but to say that I don’t care what anyone else thinks is dishonest. We all care, opinions matter. I don’t want to let anyone down.

• I am scared of how working 15 hours a day will affect my family, my relationship with my husband, my daughter’s view of her mom. I’ve tried my best to make sure that I make time for them, but it’s a constant challenge.

• I am scared of the financial impact that potential failure can have on my family. I am the main breadwinner (currently on sabbatical in that capacity:), and it’s my responsibility.

And here’s one more, which you are hearing here first:

• I am scared of finding out that I’m not cut out for this. During the past 10 years of my professional life I always thought that what I really wanted to do was start my own company. I did things on the side–like this one–but Work It, Mom! is my first full-time entrepreneurial venture. It’s been tougher and crazier and riskier and more challenging than I imagined or ever experienced before. And I am scared of ever finding out that maybe running my own company isn’t something I can do. This one is the scariest of all.

Why am I sharing this with you? Because every day I get emails asking me about how I got started with Work It, Mom!, how the site came together, how we’re building the business. I try to reply with helpful and specific points. But I want to make sure that I am perfectly clear with every single entrepreneur, freelancer, small business owner or potential small business owner out there:

CAUTION: This is scary stuff.

My to-do list is always a mile long, but I realized recently that what I do every single day, without fail, is fight my fears. It’s the toughest thing I do as an entrepreneur. And there are days when I feel like I am not sure I can keep doing it and days when I know with 100% certainty that I can. The emotional roller-coaster analogy we often hear about running your own business is extremely accurate–I am living it.

I love doing this. If something happened and Work It, Mom! never went further than it has to this point, I’d be tremendously proud of it, of our community, of everything we’ve achieved, of what I have been able to do. I have BIG plans for where this goes and some great people working with me to help make it happen. The moments when I feel like we CAN do this are amazing–I feel like a superhero! They are as amazing as getting an email from a member saying thanks for creating this community or reading a post where community members are being incredibly honest or helpful with a fellow member who needs it. That stuff is magical (so please keep it coming!)

But it’s still scary.

Do you have your own business? How do you face your fears? How do you work and push through them?

The tough trade-off between money and enjoyment of your work

When I graduated from college I was a complete idealist. I was 100% convinced that I could find a job that I liked and one that would pay me lots of money. I was unabashed about wanting both, which often surprised people. But looking back, what surprised people is the fact that I openly said that I wanted to make a lot of money, as if it were a bad thing. But that’s for another post.

I quickly got a series of jobs that made lots of money. I worked in the business world and in finance, industries that are flush with money and with people making millions in their late 20s. This wasn’t me, but by the age of 30 I was pulling in a nice fat salary, had a fancy title, and a job with lots of influence. (OK, some influence.) Except I didn’t love it. I liked parts of it, but I hated many others. So I decided to quit, give up the money, and try to do something for a living that I actually enjoy.

I can report that after six months of running Work It, Mom! I really enjoy what I do. I love digital media, I love online communities, content, interactive experiences. I knew almost nothing about these areas a year ago, before I started thinking up Work It, Mom!, but I was always drawn to them. The publishing company and the book were my attempts to try my hand at content; what I’ve learned is that I love online content and communities around it much more. I’ve found a job I love doing.

Except it comes without much money, at least for the near-term future. We’ve not raised venture capital for Work It, Mom! and don’t plan on doing it soon. (I do plan to write about our decision not to do it.) We’ve raised a bit of angel capital but we’re being extremely careful to invest it in critical things like technology and content. Which leaves me with a small monthly stipend, a tiny fraction of what I used to make in my last job. I need this money so we can pay our bills, otherwise I’d probably take even less.

And what I’ve discovered is that trading money for enjoyment of my work is really hard. I wish more people talked about this and I am being honest about it here because I want it to be OK to say things like this. There is this assumption out there–I’ve personally encountered it–that entrepreneurs who create their own companies are fine with not making money. They are passionate about what they are doing and financial profit can come second. But I don’t think this is correct, at least not in my case and in the cases of many fellow company founders I know. Working 18-hour days and constantly starting failure in the face is not easy, regardless of how passionate you are about what you’re doing. And doing this without making much money and without any guaranteed prospects of making good money makes it tougher.

Do I hope that one day Work It, Mom! is a huge financial success? Absolutely. But I know a little too much about the rarity of such success and the odds that are firmly stacked against start-up companies being successful. I love what I do and I know that I am lucky–many people never get to say this about their jobs. But my inner idealist has been tampered by this experience of trading money for enjoyment of my work. I wonder whether both are achievable at the same time and hope very much that I get to experience what feels like.

Because I bet it feels damn good.

Daily temptations

One of the things I’ve figured out during my time as an entrepreneur is that entrepreneurs only talk truthfully to each other. When I was in venture I had some friends who were running their own business and I had great relationships with some of the founders of our portfolio companies. They’d talk to me about their business, about the challenges they went through, about the ups and down, the crazy and the mundane aspects of running a company. But they never said things like this:

• If someone offered to buy me out right now, I’d be really cheap. I am so frantic and exhausted and stretched financially that they could walk away with the biggest bargain.

•  What I really want is my old job back. The one I really hated but the one that came with a nice steady paycheck, benefits, and someone else to worry about keeping the lights on.

• I talk about building up this company, but what I really hope is that someone comes along and buys us soon. I don’t even need that much money to sell, but it would be amazing validation and would make me feel like I am doing something right. Because frankly, I don’t feel that way often.

All three quotes come from real entrepreneurs running their own companies. All three are sharp, hard-working, successful, with some great careers to their name. And yet what they talk about are their temptations to not do what they are doing. To not work so hard, to not fight so much, to not be on such an emotional roller coaster.

I understand them now better than ever and what I really understand is that having these temptations in no ways means that they are not extremely passionate about their business. They We are. But it’s so damn hard to do this day after day that temptations of an easier life are natural. At least now I know that they are.

My mom likes to ask me why don’t I get my venture job back. I know she means really well – she is worried about me, my stress, the dark bags under my eyes, the lack of sleep, the frantic pace at which I am running. And I know that she knows why I left that job. But she thinks that stability and a great fat paycheck are worth it and liking your job is not something you need to aim for.  What I am doing feels like a race to prove to myself that she is wrong. So far, me and my idealism are winning — but I hear what my friends entrepreneurs say to me and I worry about how long my stamina will last.

Since most companies take 7 years to succeed (failure comes much faster) I know I have a long run ahead of me.

If you want to succeed with your business become an extrovert

I am not an extrovert by nature. Most people who meet me probably think that I am: I appear confident, I have a strong presence (at least I’ve been told), I am not shy. But in reality I am just a very good actor – I am often less confident than I appear, I don’t love large groups, and my idea of a great Saturday night is not a wild party but an evening at home with my husband and a movie.

But during my still-short stint as an entrepreneur I’ve become an extrovert. I am eager to meet new people, I strike up conversations with strangers, and I have no qualms about being in large groups. Why? Because this is the only way to succeed with starting a company.

It’s not what you know, it’s who you know. I know you’ve heard that before and so did I. But it took me a long time until I realized that it was true. For a while, the idealist in me believed that if I was good at what I did eventually it would become clear to lots of people and I’d succeed. But the world is too crowded with people who are great at what they do and in order to get noticed you have to know someone who has the power to have you noticed. Or rather, you have to know 100 people who have the power to connect you with 1000 people who can get you noticed. Because getting noticed is hard and finding those right connections is hard. The more people who know and have a stake, however small, in what you’re doing, the greater your chances of success.

Now, you have to have the goods to back up your network. Your product or idea has to be interesting/useful/unique/fun/innovative so that when it is noticed it matters in some way. But you can’t just have a great product and quietly sit in your basement waiting for the world to run to buy it. It almost never happens.

So if you’re an entrepreneur, start talking to everyone and anyone. Especially when you’re just starting out. Every day I go through all the emails that come into the Work It, Mom! info box as well as the general customer service box. The other day there was an email from a woman who works for a large advertising agency. They are working on a special promotion and she thought it would be useful for Work It, Mom! members. I wrote back to her, introducing myself as the CEO, and asking whether we could talk on the phone about the promotion. I actually didn’t want to talk about it – I didn’t think it would be relevant to most of our members. But I wanted to talk to her and I knew that I had to make it about something she cared about. We scheduled a call. Five minutes into it we realized we had a lot in common and started talking about a lot more than her initial email. The conversation went really well and I now have a relationship with someone who (a) is a great and interesting person and (b) can do a lot to help Work It, Mom!.

Had I been an introvert I would have either not replied to her email or replied with a polite “Thanks, this is not for us”. But I’ve learned to be an extrovert, to talk to everyone, and to jump onto every opportunity to get the word out there about my company.

This transition is not easy for me, it goes against my nature. But I see no other way and to be honest, it’s kind of fun.

When you feel down, focus on the small stuff

I’ve been feeling down for a few days.

If you meet an entrepreneur and they tell you they never feel down, they are lying. I used to do this, actually. I would always say everything was great and I thought that projecting confidence was what I should be doing as the founder & CEO of a company.  But it’s dishonest and it has a real drawback: If you never tell people about issues you might be having you can miss out on good advice or help they could offer.

So I try to be honest. And today, I’m feeling down.

There is no specific reason – we’re making progress, traffic numbers are growing, we’re getting some press recognition, and we continue to get amazing feedback from members. But we’re not growing as quickly as we’d like (is anyone?) and my email is strangely quieter than usual. This worries me. I use my email as a barometer of activity and initiatives we’re pursuing – it is usually filled with dozens of new emails that demand my attention. (Of course, then I complain about too much email…) It’s not a holiday, the summer is over, and when my email gets quieter I get worried.

It’s easy to become completely wrapped up in feeling worried and down. But it’s useless. I’ve realized that to get through times like these what works is to focus on the small stuff. Small to-dos, small bits of good news, small achievements. Getting stuff done makes me feel productive; worrying about the BIG PICTURE makes me less efficient.

I am sure there is a self-help guru out there who has come up with all sorts of deeply researched reasons why this works. I only know it does because I am doing it right this minute. Instead of worrying about my business I am doing something that’s been on my to-do list for a long time – write a post for my Learning Optimism blog.

How do you deal with feeling down or worried about your business?

5 Dark Secrets: What (Almost) No One Tells You About Starting Your Own Company

Before becoming an entrepreneur I worked with many of them closely for five years. I watched them start, grow, exit, ruin, and shut down their companies. You’d think there would be few things about starting a company that would surprise me. You would be wrong.
During my still-very-short tenure as an entrepreneur I’ve discovered many things that have surprised me. Here is my list of 5 Dark Secrets of Entrepreneurship. I’m sure it’s not exhaustive.

1. An entrepreneur, you feel stupid much more often than you feel smart

Most entrepreneurs I’ve met in my time as a VC were really smart. Not all had good business ideas or solid management skills, but they were sharp. At the risk of sounding self-indulgent, I think of myself as a generally smart person. And yet, as I’ve been working on launching my company, I’ve felt dumb and stupid more often than I care to share. I’ve made bad decisions, wrong choices that in retrospect seem so easy to have been avoided, and I’ve learned a great deal about things I thought I already knew a lot about. Entrepreneurship is all about trying and building new things. Regardless of how smart you might be, doing something completely new and making endless mistakes can be stupefying.

(Now, I’m no Marc Andreessen and perhaps after a few billion dollar companies under my belt I’d feel less stupid starting my next one, but I’m not sure. Maybe I’ll email Marc to weigh in on this.)

2. Everyone is your greatest fan when you start, but support wears off quickly

When I told friends and business contacts that I was starting my own company, the enthusiasm was overwhelming. It was like going from one cheer-on session to another, with tons of encouraging emails and calls sprinkled in between. It felt great and gave me a lot of confidence about what I was doing.

But this overwhelming support began to wear off as time went on. The big news about my new gig wasn’t news anymore and support quickly turned into feedback. Feedback is great – it’s useful and necessary. But it came in heavy non-stop doses. EVERYONE I knew wanted to give me tips on everything from what our website should look like to how I should word our email newsletters. Emails that began with: “Hi, I was just checking out your site and wanted to give you some advice,” became very frequent. I found myself with a strong urge for those great support-filled emails that flooded my inbox earlier on. As maybe too few entrepreneurs will tell you, we need as much cheerleading as we can get.

3. Regardless of your confidence level, you will often experience crises of confidence

Most entrepreneurs I know are generally confident people. I don’t think it’s possible to take on the enormous amount of risk starting a company requires without being confident in your ability to overcome it. Apparently experts agree, which makes me even more confident in this assumption.

But being an entrepreneur involves consistently overcoming crises of confidence. You feel hopeless about making progress, you think your business is doomed, you think you’ve made the worst decisions ever. This is a crisis of confidence and you have to work very hard to overcome it. It’s a horrible feeling.

4. Nothing is ever right on the first try

Your website design needs to be re-done. You hired the wrong sales guy. You strategy is wrong. Your name is spelled wrong on your newly ordered business cards.

Nothing works on the first try and regardless of how much you expect this, you feel crushed when it happens and you think you’ll get it right the second time around. Sometimes you do, but often you don’t. Our company is four months old and we’ve redesigned the homepage twice, modified our focus, changed many of our tactical feature implementations. Intellectually, I knew this is part of the process – everything is iterative and you learn only by doing. Emotionally this is rough because it often leads to #3.

5. You will take everything personally

This morning an email came into the info box. It was from a woman who is married but chose not to have children. She spent three paragraphs writing about how prejudicial, judgmental, demeaning, biased, and damaging it was to create a site for professional moms (vs one for professional women). I read the email quickly and moved on to the next one. But it kept nagging me as I worked. I wanted to reply, to tell her the many reasons why I disagreed with her. I took it personally.

Now, some of you might want to dismiss this as a woman-thing, but don’t. I’ve now met enough entrepreneurs who say this is true – and they never admitted it to me until I became one of them.

What am I missing? Share your favorite dark secret of entrepreneurship in the comments.