Lessons of a Reluctant Entrepreneur


Last Friday, Rhea and I headed into Albany to attend Social Media Breakfast, a local event Rhea was speaking at alongside Mike Germano and Stuart Foster. While we were there, we met some incredible new friends. People who were excited to learn about social media and the potential benefits it could have on their business. Rhea, Mike and Stuart were there to share tips, strategies and their own experiences. I’m probably biased, but Rhea totally rocked it.

After the presentation, we got to talk to many of the attendees. We talked shop. We talked about Troy. We answered questions. One natural question everyone had was, “How long has Outspoken Media been together?” I realized in that moment that it will soon be six months. Six months since Rhea and I threw caution to the window and began writing the true story of Outspoken Media. I thought six months sounded like a good amount of time to stop, sit back and reflect on lessons learned. Plus, I head to Canada  tomorrow to spend 12 days with Rae. I may not survive.

In case you missed it, we’re in a recession. And yet, people are saying that right now is the perfect time to start a business. And if that’s the case, I wanted to share some of what I’ve learned about myself, about being an entrepreneur, and about waking up every day and not having a “job” to go to.

Here have been some of my lessons in being a reluctant entrepreneur.

Work when it hits.

The majority of my work is highly creative. I write. I blog. I tweet. I engage. I build. And that’s not always something that you can force. In order for me to stay efficient and to always have something ready to go, I need to work when the fire hits and not stop until the flame has died. Usually that means there are a few nights a week where I’m pulling days that don’t end til 3am-4am. But I need to do that and I’ve actually come to enjoy it. There is nothing like those nights when you’re on fire. When you’re on your 7th cup of coffee and Twitter is quiet because even the folks on the West Coast are in bed. Those are the days where I’m able to knock out client work plus 4-5 long posts that I can schedule for later in the week. It’s the quiet moments in the middle of the night where I’ve done some of the stuff I’m most proud of. And I know that if I don’t take advantage of those days when the flame is strong, that later I’ll regret it when I can’t write my way out of a paper bag.

When the passion hits so hard that your hands are trembling, use every ounce of it. You can always sleep in an extra hour or two the next day.

Don’t trivialize what you do.

SmallOne of the biggest struggles we initially faced at Outspoken was really understanding what each of us brought to the table and bleeding that. [Okay, maybe it was just me and Rhea who struggled with this.] The two of us were both new to this whole thing and there was a bit of doubt in ourselves and, to be fair, sometimes each other. Even now, I can recall some of the early conversations Rhea and I shared and it makes me wince. Insecurity is contagious and it spreads like a disease. When you don’t believe in yourself and what you bring, you cause others to question it. You open the door to being micromanaged. You walk softer than you should. And there was a lot of that the first month of Outspoken. And then it stopped. And when it did, we became more efficient, more productive and started kicking 200x more ass.

There is no time in startup life to be insecure about your talent or whatever anyone else brings to the table. You need to understand it from the very beginning and then bleed it out of every pore. If you’re always questioning yourself and putting off your responsibilities due to fear, then you’re sabotaging the company and you should get out now. That first month of Outspoken sucked at times, but we’ve conquered it and we’re better for it.

How to spell ‘entrepreneur’.

Yeah. That was a tough one. It deserves a mention.

Ignore people who try to offer you a job.

I’m offered a “real job” at least once a week. The offers come from very well-intentioned folks who want to help and offer me a position with benefits and a salary and real coworkers. They want me to know I have options, you know, should I want to jump. And it’s all very sweet of them. Except for the fact that I have a job. It’s running Outspoken Media, building a brand, and managing the content, communities and voices of our very awesome clients. So, no, while I much appreciate your job offers, I already have one. Thanks for thinking of me.

Don’t let people’s need to keep offering you stability make you question your own.  You’re good.

Create your virtual water cooler.

office water coolerI may have a job, but it’s sometimes an isolating one. I work alone out of my apartment for 10-14 hours a day where the only things I have to talk to are Jack and Swat. As cute as they are, cats suck for conversation. They also don’t appreciate my totally funny jokes. I think somewhere along the line I was supposed to make “non work friends”, but…shut up, I never did.

Because I don’t have a physical office, I’ve created a virtual one. Skype has become an essential work tool for me. It allows me to pop my head over the cubicle whenever I need it. If I have a question, need advice, or just have a funny story to share, my fellow “coworkers” are there to listen. We’ve created our own mini network, complete with Friday happy hour. I’ve also built a schedule for myself where I’m working outside of my apartment in wifi-enriched coffee houses a lot more. Getting out of my apartment tricks me into thinking I’m really “coworking” with all the other people sitting around me. It also means I get to talk to new people and gives me a reason to shower and change my clothes on a daily basis. These are all nice things.

I don’t know what it is, but getting out of the house and working where life is happening and where people are excited…it helps. Use it.

Actually, I don’t have a job.

I take back that previous one. This isn’t a job. It’s simply a lifestyle that I have chosen for myself because I am part ambitious, part masochistic. And the sooner you accept that about yourself, the more content you’re going to be living it. You may even like it.

Commiserate with other entrepreneurs.

Sometimes when you work alone and you’re putting in crazy hours, you feel like you’re crazy. You forget why you’re doing this. Why you love this. What the goal is. And the only way to overcome that is to surround yourself with people who are equally crazy and obsessive about their work. Because you’ll find your reason in their passion and their excitement. Oftentimes, this means hanging out with other entrepreneurs because, frankly, they may be the only other people who will really understand.

I’m not saying entrepreneurs are “better” or “strong” or “smarter” than people with 9 to 5s, I’m saying that when I met Mike Germano last week, I could see in his eyes that he understood exactly what I was feeling. When we sat down to chat after Social Media Breakfast and I started rambling and venting and being oh-so-happy for human contact, I knew he was right there with me. He gets the struggles. He knows the fear we all pretend we don’t have. By being able to share war stories, to complain, and to commiserate with people who get what you’re feeling because they’re going through the SAME THING…it’s invaluable. And then you remember that you’re not crazy. You’re actually incredibly blessed. And you get back to work.

Praise is to be feared.

applauseThe SEO community has been amazingly welcoming and supportive of Outspoken Media. Truly. The support that we received out of the gate, and the support that we continue to receive, is overwhelming. And we’ve tried really hard to be worthy of that support. At the same time, each time you tell me something positive, I’m half ignoring you. I’m sorry for that.

If I think I’m doing a good job, then I’m not motivated to do better. If I think this is “good enough”, then I start going to bed before midnight. I become content. I don’t ever want to feel content in my work again, because I’ve been there, and that’s when I’ve let jobs get boring. When I’ve let them become routine. Ignoring praise and telling myself I need to work twice as hard for your love is what motivates me. It means I’m always clawing my way up. I’m always growing. Outspoken is growing. And Outspoken means the world to me.

If you can accept praise without losing your fight, you’re ahead of me. Ignoring it helps keep me motivated, so that’s what I try to do.

Six months probably feels like a relatively short time to be in business, and I agree, it is. But I think the lessons you learn in your first six months of entrepreneurship are things to be treasured. Because you learned them the hard way. And you earned those war wounds. And frankly, most of you didn’t think we’d survive this long. ;)

I’ve love to hear some of your greatest work and life lessons.  Please share. I may die in Canada.

Your Comments

  • @joannalord

    Refreshingly honest and 100% true. In telling your own story, you tackled so many of the challenges we are handling…everyday. Thanks for writing, and congrats to you ladies on hitting the 6th month mark!

    P.S. You had a typo…you meant: When you’re on your 7th cup of coffee and Twitter is quiet because MOST of the folks on the West Coast are in bed. :)

  • Hannah_Bo_Banna

    I loved reading this post Lisa – particularly the part about self-doubt. I think it’s something that we all suffer from.

    I wish you ladies all the best for the next six months and beyond.

  • MikeTek

    Lisa you suck. This post is just not up to snuff.

    I’m about 8 months in myself – a totally bootstrapped operation with zero, I mean zero, seed money.

    It is rough, for all of the reasons you stated above and then some. I’d love to say the SEO community welcomed Unstuck Digital from the get go but I’d be kidding.
    Not to say people haven’t been nice, they’ve just, eh, not noticed. A lot to be said for this quote from Henry Ford:

    “You can’t build a reputation on what you are going to do.”

    Some of the most important things I’ve learned:
    – Face time is crucial. The people you sit down with, break bread with and laugh with are the people who’ll be in your corner
    – Routine breeds good habits. Self-employment means you do what you want when you want. That’s a double-edged sword – I’ve burned more time than I’d like to admit fruitlessly.
    – It’s lonely. As you stated above. Lonely as hell. Now my friends wonder why I’m suddenly so chatty when we hang out. Working for yourself often means working by yourself.
    – Being outwardly human, not stiffly “professional,” yields the best response. People don’t want to hire a company, they want to hire good people. Especially in this business. Trust is paramount, and any jackass can slap a logo on a business card and call themselves the “CEO and Founder.”

  • Lisa Barone

    Joanna: Haha, touche. :) It’s true. When the middle of the night hits and I need someone to vent to, I know that you’re still up and only a DM away. It’s one of my favorite things about you. :)

    Kenny: <3

    Hannah: Thank you! I'm really excited about the next six months and what the future holds. I barely feel that pit in my stomach anymore. :)

    MikeTek: For what it's worth, I've noticed you. I know your blog and that you have LI roots. :)

    You share a lot of really good lessons. Especially the one about how easy it is to burn time. Yes. I've wasted far too many hours doing stuff that does not benefit me. That's still something I'm working on. Damn Twitter to hell!

  • Steve Early

    Yeah, not that great. Go to Canada and try to have fun. This reads like you need a break or something.


  • Brian Clark

    I agree with Kenny, Lisa… you suck. Please try harder. ;-)

    No, seriously… it’s been fun watching you evolve over the last 6 months. And it never stops, so keep going.

  • Charlene Burke

    Excellent points and well said Lisa. I’ve been developing my info pro business since August ’08 and my online marketing business since March ’09 and so far, so good. Having said that, I’m really glad you mentioned Skype. I have a teleconferenced MasterMind meeting that I attend and the other members are in the same business as I am – and they’re invaluable for providing insight and encouragement. But, after meeting a few of them at a national conference just recently, I realized how valuable face time is – so I’m taking your experience and will be suggesting to each of them that we meet via Skype.

    Speaking of face time, that is the most important aspect of business development for me. So many people do not understand what an info pro does, but when they hear me describe the many projects I have done, and how enthused I am about possibly working them – then they’re on board.

    Miketek’s “being outwardly human” really hits home, too. I have to leave my corporate professional image behind and move forward with just being me – the techie, the geek, the trekkie, the “I hope there really aren’t aliens, but until it’s proven I’ll collect all kinds of figurines” person and the non-girly girl who laughs often and tries to be optimistic in these times of pessimistic thinking :)

    Great post Lisa!

  • Robyn

    I think that was a brilliant post! Very honest and true. I have saved it to share with others and refer back to myself. VERY GOOD. Thanks for sharing it.

  • Michael D

    It was all good until that cheap shot at West Coast slackers. Here in LALA land, we require our sleep. :)

  • amymengel

    Congrats on hitting the six-month mark! Rhea definitely rocked it at SMB last week and it was great to meet you guys and see your passion, knowledge and kick-assness in person. Hopefully we can keep growing a stronger social media enthusiast community in this area.

    And yeah, entrepreneur is a friggin’ annoying word to spell. I had to scroll back up to the top of this post to make sure I didn’t screw it up just now.


  • Jim Kukral

    I enjoyed this, and resembled it :)

    I have been working with what I call “accidental entrepreneurs” for some time now. They lost their jobs, and don’t have job offers like you do. So they have no choice but to go for it.

  • Therese

    This is an excellent post, and not to be repetitive, but true on so many counts. I am self employed and work from home so i feel you on the boredom of being in your home constantly. I miss that stimulation a great deal, I have went to Starbucks and worked before and I am going to join PRSA and get involved in my local chapter along with trying to look for other events put on by the Social Media Club, etc. I think those things will help.

    I still struggle with self doubt, although I am working on it everyday I still question myself, that is more of an issue of overcoming all of my past which is a whole other comment, or post, book – something like that.

    What I have noticed that has helped me with my self doubt is going to conferences, you hear industry leaders speak and you think the same things they do, you are doing what they are saying is right, well my own variation of it anyway, so that boosts my confidence and honestly to network with others and to see that you gave them a new perspective on something, that you are helping them grow – that has helped me a lot and hopefully helped them at the same time.

    This is an excellent post, another for my ‘library of clips’

  • Therese

    Oh and I left something out

    Congratulations on Hitting the 6 Month Mark!

  • Emory Cook

    Thanks so much for your wonderful post! I started my own business in February and I’ve never done anything more exciting, more exhausting and more frightening! But I love it, and I’m thankful to read about the experiences and lessons learned by other entrepreneurs. Some of your points (particularly not trivializing what I do) really hit home.

    Thank you for the encouragement and advice!

  • jlbraaten

    That feeling of half-ignoring praise reminded me of when I quit smoking. People would say “good job!” all the time but I was almost offended. It was my victory and something that I needed to do for myself. I can see you how your experience as an entrepreneur can produce this similar feeling.

  • Stuart Foster

    Crap…it’s been 6 months? I feel like a freakin’ slacker by comparison. Although, I’ve evolved from 2 people ever hearing of me…to maybe 10. So I’m pumped on that account.

    Also…half of my excitement comes from the sheer fact that I am still learning and growing so much through reading, talking and experiences with other entrepreneurs. (Granted I’m not one…yet.)

    Don’t die in Canada though. That would kind of suck and greatly diminish the quality of my reading material/entertainment for the week.

  • Joe Hall

    HOLY SHIT! That pretty much sums up how I have been feeling for the last two years! Amazing!

  • Joe Hall

    Oh sorry for swearing, never done that before on another person’s comments.

  • Todd Mintz

    Truthfully, a full night’s sleep every night is your ally not your nemesis…try to remember that :.)

    Other than that, this post kicks ass…you’ve certainly evolved a heck of a lot since starting this company and it’s great that you share your thoughts so openly and passionately.

  • Rae Hoffman

    Joe, I’m highly offended that you have soiled our blog.

  • Joe Hall

    I am sorry Rae! I will try harder to keep my language at the same level of cleanliness that you regularly adhere to! ;P

  • Gil Reich

    This is a great post, Lisa, thanx.

  • Anthony Verre

    Somehow I feel like my psyche has been cleansed after reading this post. And, while not out on my own just yet, it’s the homework before storm, so to speak that’s already got me feeling many of things you talked about in the post.

    Right now I am working a long, long 9 to 5. And, when I get home, I break out the laptop, open up WORD and start pushing out content for the business I’m going to build in the next 3 to 4 months. You burn the candle wick to the nub. You get your 6 hours and do it all over again.

    What actually keeps me going:
    1) Fear of failure.

    Not many will admit that. I failed enough times in my life to know exactly how much I hate it.

    2) I don’t know how to fail.

    While it may seem contradictory to #1, it’s not. It’s something that’s ingrained in me, I guess. I would rather die than admit/submit I cannot make something work. I will push myself until I’m standing all alone at the edge, every boundary broken. It’s a killer instinct I can’t unlearn and wouldn’t want to.

  • Clint

    This article offered some great encouragement. As a small business owner, it can be easy to get discouraged and second guess yourself. I appreciate the thoughts, especially the section about not trivializing.

  • The Mules

    This is utter clap-trap, though we did not read it.

    We arrived via Bing for an unrelated term. Our Blackberries all work flawlessly — and are edible, too. Our cats are more fun, and, unlike yours, have been trained to laugh. We shall survive Canada Day, even should it become Canada Dry. The pig has rolled himself into a bacon explosion to get our attention. Streko is clanging around in our Skype window, begging us to pick up so he shows unavailable.

    We interviewed your barista — she reports you need a new liver, that we just missed Robert, and that you owe her $5.91, plus tax, for a broken glass. We covered your tab. She said our manes were shiny. And adorable! screamed another patron. He had no recollection of you, based on our description — we then produced a photograph, in which you are depicted after an evening of livebingeing. “Oh that one,” he said, and would not further comment on the record.

    Kenny Hyder informed us this post was written in PowerPoint. It is concerning in its similitude to the Wikipedia entry on Jamie Varone. Last night, Chris Pearson gave the whole herd a sweaty liniment rub-down. In his skivvies.

    But all this can only mean there’s room yet to grow and enjoy. From the mule barn to your internet family, Happy Halfaversary — keep kicking ass, ladies!

    Disclosure: This is a paid endorsement for the Brassbits Feedbag Emporium — get your mules the grass that lasts.

  • Kae Kohl

    You know you’re at a great blog when the comments are as worthwhile as the post. Thanks for summing up so much of what we go through.

    My struggle, like others, is the time burning. Somehow, every day seems like it’s a week long (in a good way), yet slips by in a minute. So precious a resource, so easy to waste. Grr. I think your idea of “work when it hits” could be the ticket. Other suggestions welcome. And, happy semi-ann.

  • Laura Rucker

    Wow, what an awesome post and highly motivating. Thank you so much for your words of entrepreneurial (did I spell it right?) wisdom. I’m looking forward to reading your past and future posts. :)

  • Gerald Weber

    I can totally relate to everything you said in this post because I pretty much operate in the same manner you are describing. Skype is the water. I sometimes find myself doing work at 3 or 4 am and I get job offers all the time lol. Sometimes I run into friends I haven’t spoken to in years and they are like ” are you still doing that internet/website thing?” lol

  • Ken at HCG

    Damn! Summer already?! I best get to bed!

    Well said and straight from many of our lives I am sure. I know I am certainly the king of binge working. Except it seems this past year has turned into one long work binge with one day running into the next. Month into month… Somewhere it seems I have forgotten to take a break. I’ll take a break just as soon as I finish this one last thing…and perhaps that other last thing…
    sigh….oh well.. At least I got good SERPs in a tough market from it all! Keep sleeping Amazon! I haven’t been! :)

    I always love a short walk outside at 4:30 AM just before the dawn…..and just before bed. It iss a great time to reflect and think about your next step. The birds are just beginning to awake, the air is crisp, dew is on the grass and there is no one about to disturb your deep thoughts as everyone is sleeping at that time……except you and Gerald and Laura and Kae and…

  • Dr. Pete

    Great stuff – I’m 3 years into working for myself, and am still learning some of this, so you’re clearly a lot smarter than I am :)

    I remember the day in grad school when I realized I needed to “Work when it hits”. I always believed the hype – you’ve got to just “pound away”, “put your nose to the grindstone”, blah blah blah from 8am-5pm and do your work when the powers-that-be say to do your work. Meanwhile, I knew that I’d have these bursts of amazing energy and superhuman productivity followed by a lot of staring at the walls. When I worried about doing it the “right” way, I wasted the energy and tried to force my way through the down cycles, getting nothing done and making myself miserable. Being able to recognize and use that energy, and not freak out when I don’t have it is one of the most important work lessons I’ve ever learned.

  • John Polhill

    It’s a challenge no matter how long you’ve been in the self-employed business.

    I just keep saying I’m getting closer to my goals everyday that passes and that today is going to be the best day of my life every morning!

  • Jamie

    Great post Lisa, its true being an entrepreneur isn’t a job at all. Its a lifestyle, and none of your “non-work” friends will ever get that. Why can’t I make the party Friday night, not because I’m working, but because I am building. And building things is cool.

  • Alison

    First Lisa, welcome to Canada. Don’t know where about you are going to be in this vast open space of ours (many places for Rhea to hide the body…) but I hope you find us as accepting as our cliche image suggests.

    I just came across your blog (tweet from Alyson B. Stanfield) and it is refreshing. Both my husband and I are self-employed and work from home. Much of what you say rings true – the need for social interaction, the fear, the lack of getting it from the 9-to-5 world (if I hear one more moan from the on-a-fixed-income crowd… grrr….) But, tough as it is, a crappy job, working for folks you can’t respect is so much worse. So, I’ll be checking in when I need a little refresher.


  • Tom

    Wow – great post to find at the start of another day at the grind! If you could bottle the ‘problem shared’ feeling, Red Bull would be out of business!!

    Will pass this on…!