Business Lessons From A Still-Reluctant Entrepreneur


It’s been a year since I shared some lessons from a reluctant entrepreneur. In that time, Outspoken has thrived and swelled in ways I couldn’t have imagined. As we approach our terrible twos, our legs are sturdier, the brand is stronger, and we continue to fall in love with our clients. Of course, it hasn’t been all rainbows and head pats. We’ve also had our share of scraped knees, bruised egos and days when I’ve wanted nothing more than to egg Rhea’s house or drive to Guelph just so Rae could see me roll my eyes at her in person. But 18 months into Outspoken’s life, we’re solid and we continue to learn and grow. And that’s something I’m thankful for every day.

As I shared earlier, I’m going on vacation next week. In fact, I’m scheduled to leave in a few hours. And should the oily gulf swallow me whole, here are some new lessons from a slightly less reluctant entrepreneur.

Fix small problems early

When you first start a relationship, everything they do is adorable. It’s cute that he talks through movies and it’s endearing to watch her chew with her mouth open. It’s not until month eight when you start secretly dreaming of strangling your partner with a pillow just so he’ll STOP TALKING! The thing is, had you mentioned to your beloved that you actually wanted to hear the movie he probably would have just shut up. But you didn’t mention it. And, well, now you’re in jail for his murder.

At Outspoken, we’re pretty good at squashing issues head on. But it is something we constantly work to improve. Sometimes we would allow small problems to fester too long. We assumed it was easier to swallow it than to risk upsetting someone or earn a flying elbow. Speak up. Speak up at the first sign of issue and speak loudly enough that everyone can hear you. That’s how the company learns, how it syncs and how you’ll make it to your one year without a toe tag. Things don’t get better when you grin and bear it, they get worse.

Respect yourself first

Perhaps it’s the father-instilled Catholic guilt, but I will inconvenience the hell out of myself not to trouble someone else. [I’d blame my mother but she just started talking to me again.] But over the past year I’ve learned a really valuable lesson. Saying ‘yes’ to every phone call with someone who wants ‘just five minutes’ doesn’t make me approachable, accessible or a great community manager. It doesn’t show that I am invested or that I care. It makes me an idiot and teaches people that my time isn’t worth much. Flexibility is one thing, door mat is another. As I said a few weeks ago, if you want people to respect you then you have to respect you first.

Seek out different views to understand them

One thing I believe hindered me in past jobs is that I stayed pretty firmly in my bubble. I knew what I did, why I did it that way, and was confident in that. I did okay, but I wasn’t learning. What I was doing was making myself indispensable. That was dumb.

One of the great things about the team we have assembled at Outspoken Media is that we approach things differently. Rhea and Dawn see links, Rae sees traffic and I see brand. By seeking out the girls’ viewpoints and opinion on things, even if I have no plan to change how I do things, it opens my eyes to new possibilities. I learn things that make me better at what I do. When you step out you often learn stuff that is so common to someone else and yet never would have crossed your silly little mind. Like actually using keywords in posts if you want to rank for those terms? I mean, WHO KNEW? Using Title tags? INSANE!

Use microaction

During last year’s Expert Week, my friend Gwen Bell mentioned something called microaction when talking about how to be an entrepreneur without leaving your 9-5. Gwen said:

Microaction Do a bit of this now. Not tomorrow. And see the microactions stack up.

Microaction allows you to remove the fear behind a project by just taking a nibble. If I nibble a blog post at night, it means I’m left better to attack it in the morning. If I nibble at a client project before lunch, it means that after lunch I’m already started and in the groove. Choosing microaction (instead of procrastination) has pretty much saved my life. Or at least others from killing me.

Learn limitations, don’t assume them

You may have noticed that I don’t speak at conferences or do audio interviews. I can’t do it. And I don’t say “can’t” as in I don’t like to or that I feel I don’t have the knowledge needed. I can’t because I have a speech disorder and my biggest fear is taking away the value of the conference for someone in attendance.  I would never want to do that. And that’s always been a limitation that I’ve accepted without testing. I’ve always taken the ‘just say no’ approach to industry speaking, even though it kills me to have to do that. It’s frustrating to turn down the same conferences that others would sell their first born to speak at, especially when I feel as though I am letting Outspoken down.

This year some things changed. I recorded a podcast interview with my friends at Bruce Clay, Inc. I also did some other audio interviews, some of which aired and others that still sit on the cutting room floor (and inspired dailybooth pictures like this). It’s difficult to put into words what it feels like to expose yourself in a certain way, but I’ll tell you that doing it has, in a lot of ways, recommitted me to NOT doing it. We all have limitations and we have to accept them for what they are. But there’s a difference between learning what your limitations are and assuming out of fear. While my decision to write instead of speak hasn’t changed, there’s some comfort in knowing that I gave it a try.

Your strengths are also your weaknesses

Let me just address myself here for a moment:

Lisa, the fact that you’re ‘outspoken’ and honest on the blog is one of your greatest writing strengths. Trust that and never lose it. However, it also makes some people want to punch you in the face when you speak to them. Realize this and correct it. Sometimes it’s okay for you to STFU for a greater good.

Leave the pack

It’s funny, you start your own business to do things your way and follow your rules… and then you instinctively revert back to being a pack animal. You go to the same conferences, use the same lead channels and become a complete replica of everyone else. During a recent partner meeting, the three of us sat down to examine what we were doing and saw some areas where the company was definitely guilty of pack mentality. We took a look at how we were spending our time, where leads were coming from and where time was being wasted. The trick is to work smarter, not harder and not identical to anyone else.

Remember the joy

Enjoying what you do matters.  If you lose that, you lose the fire, the drive and the reason for what you’re doing.  Find ways to work joy into your process and to realize how lucky you are to be doing what you’re doing. And if you don’t feel lucky, then you need to start doing something else.  Because you spend too many hours at work not to enjoy it.  Also, people can tell.

You can do only what you can scale

I like to consider Rhea, Rae, Dawn and myself pretty awesome. However, as awesome as we are, we’re still four people. And that means scale becomes essential if we’re going to continue to grow and service our clients the way that we want to. And it’s around that time when horrible, horrible words like ‘delegating’ and ‘outsourcing’ get thrown around. I think these words suck.

I take a lot of pride in what I do. I have standards for myself and for Outspoken and one of the hardest things I had to do this year was to interview interns to come join the team. And while I kicked and screamed and hated the entire process, I know that we’re doing our clients a HUGE service when bring in others and hold them to our standards. Sometimes I need to get over myself and my issues and give up control just a bit. It’s usually okay. You can only survive on sheer will for so long.

Those have been some of my biggest lessons over the past year. What about you?

Your Comments

  • Gil Reich

    Terrible twos? Does that mean you girls are going to be more “outspoken” this year? Uh oh. Time to toddler-proof the internet.

    Seriously though, nice post. You make good points about weaknesses, which you talk about a lot, which is great. But I wonder if you think enough about your strengths. For example, you’re a fantastic writer. I assume you’d advise a brand to think a lot about their strengths and the different opportunities they open. An entrepreneur needs to do the same. I think people often think “this method works” when the truth is “I’m very good at X and therefore this method works for me.” The advice about owning your weaknesses, finding your joy, leaving the pack, etc. is great. But people should remember another key part of individuality, their strengths.

  • Lisa Barone

    A very valid comment. I think I’m aware of my strengths. I know that my ability to write, to engage and to break down complicated concepts into simpler ones is something that makes me very valuable to both Outspoken and to clients. I focus on weaknesses because I think I learn more from examining those than what I’m already good at it. I also think too many people focus on what they do well instead of pinpointing what they don’t.

    But you’re right. It’s also really important to know what you do well and how to leverage those most effectively. Thanks for the comment! :)

  • David Mihm

    “horrible, horrible words like ‘delegating’ and ‘outsourcing’ get thrown around. I think these words suck.”

    Couldn’t agree more…hence the reason I haven’t expanded beyond a one-man consulting shop. It just seems like so much energy to find people that you get along with well enough personally, that have the energy and inclination towards what you’re doing, and that are willing to accept what to you/me seems like a reasonable intro wage.

    Really glad to see that you guys have been able to do it & I am looking forward to seeing who else you hire in the next year!

  • Indian Marketer

    The last one is something I’m struggling with. I’m too much of a control freak to like delegating, and yet I need to do that in order to focus on the more important things.

  • Amber Jordan

    18 months really? I’m shocked! Just remember that beyond the terrible twos..comes the terrific threes. I love your point about leaving the pack and then finding yourself back on track with the same folks you ran screaming and yelling from. Thank you for your honesty and “true to thine own self” rants. I’ve enjoyed following you and have no intentions of letting a couple of toddler meltdowns get in my way. Toilet locks are in place and all un-washable markers have been thrown away. Bring it on!

  • Clare

    Just keep them coming Lisa – your words are like life rafts for those who are still working the 9-5, raising a family and keywording at 3am. So glad I found you & Outspoken

  • Alan Bleiweiss


    It’s obvious you’re passionate about what you do – and explains why you’re as happy as you are in that. And the fact that you’re humble, (to the disbelief of haters, of course) just reinforces why you’re so well respected in the industry by others who are themselves successful.

    So I’ll offer this more an expansion/reinforcement of what you’ve already stated than something different… Truly worthwhile success – the kind that results in untold happiness as well as the rewards that come from that success, comes from being humble while being confident in your strengths.

    The more you focus on what you’re passionate about, the more your strengths will shine through. And the more you honor those limitations you learn about yourself and your business, the sooner you’ll seek out others who are passionate about things you’ve got limitations with. Whether it’s co-owners of the business, employees, or outside partners.

    I think that reality is what makes my clients so loyal to me. When I don’t screw up, that is. :-)

  • Lyena Solomon


    I really liked “Respect Yourself First” lesson and I hope it is at the top of your list for a reason. I cannot agree with you more on this. It is such a simple concept and so difficult to execute.

    Having been a consultant for 10 years, I always try to be helpful and make time for everyone who asks for my help. I have technical background and work with clients who do not. Therefore, I am often summoned for consults on all topics because everything web related is becoming somewhat technical. It is very hard for me to say “no” to people if I see that I can help them. I realize, however, that often they do not really want my help. They want to chat and to vent their frustrations. Spending most of my time chatting and not doing anything is not my style (and I do not charge by the hour).

    I found a way to say “no” by not saying it. I ask the client to research the problem more. I request information on what they want to accomplish, how others deal with similar issues, what the possible solutions are, how this issue impacts their business (ask for numbers and stats), etc. If my client feels strongly about resolving the problem, they will come back with results. Frequently, in the process of gathering the information, they find their answer. If the client is not willing to do the leg work, then the issue is not important to them and I am “off the hook”. I can sleep well, knowing that I did not let them down.