I too am a small business owner at the age of 25; however, I have been called cocky and humble at times…so I googled “being cocky” I have no shame In what I have accomplished; however, there are times I do pat yourself on the back, it’s human nature. I do believe that keeping my accomplishments to myself and listening to other people talk helps me out in a magnitude of ways. So my suggestion is stay humble and listen to people, It has helped me out.

Many of my work colleagues do have that cockiness that you speak of that puts people off. I’ve often found that it is because they don’t like something about themselves or are insecure, and the bravdo helps them to hide it.

I’m more of the mindset that you have more strength through humility. If you are generous in your conversations with people and allow them to talk more about themselves (as stated above in other posts), they will open up more and see you as trustworthy – perhaps something you don’t see in yourself yet? Deflecting attention away from yourself allows you to keep your privacy, while at the same time being socialable.

Best to you.

To grow your business, you may try expanding into the world of online marketing, not because it is cool but because overhead is so low. You already have a blog and have an idea how to drive traffic to it. ebay has an affiliate program, amazon, … everyone out there seems to be looking for eyeballs. Maybe you are doing this already, maybe not. Why not write an ebook about dealing with debt, financial planning and all the other things you offered here on the blog and market it? That seems to me like a great low-overhead project that can bring in some cash. Combine that with a affiliate site of sorts and you will have a low-overhead growing business.

My personality would also require of me to learn to trade profitably (with demo accounts) and then go back and make pips down the road. This requires a significant time commitment, so it may be better to leave it for later.

Every adversity has a bright side and a dark side. If you focus on the bright side (learning experience and focus you gained from it), dark side can be shelved in a, well, some dark place where it won’t get in your way. Pursuing business goals is often the best distraction from things that cannot be changed.

I think you would be even more successful in your business and possibly in social settings if you left “past transgressions” and “quarter of a mil” thinking on a shelf somewhere, instead of wearing it like a ball and chain. You have your business, you got bills to pay and you are doing a great job. Most people would just fold and sit in a bar somewhere. As a business owner, treat yourself like a business man. In social settings, there is nothing bad with coming across as a hard-working person. If you insist on your “transgressions”, trying poking a controlled fun at yourself (Made a lot of money, blew a lot of money “ha ha”) and move onto another topic (where you grew up, what sucked and what did not suck and oh wait they just served the punch). You can also reduce your “business talk” to not liking 9-5 grind, working for yourself, building a customer base and learning an MBA in school of hard knocks (that should come across as a bit of fun).

Focus on your business and good things about it. Too many people focus on bad things and negative things about themselves. You should keep those on the shelf somewhere, but to move forward you have do good things for your business over and over again and move on after you make a mistake.

All the best.

@ No debt plan – I’m trying to get out more. I’ve actually been more “social” the past month or so. It’s still a tough balance for me. I’m sure whoever I interact with thinks I’m just a little shy.

You can’t get better at any skill without practice. Put yourself in more of those situations. Go out in groups and get comfortable talking with folks. It won’t happen from just sitting around at home.

As far as being considered cocky goes, are there other things that you can discuss with confidence besides your business? Hobbies or other interests? There is nothing wrong with being confident when talking about your business but,as a girl nothing that turns me off more than listening to a guy talk about how much money he makes or how great he’s doing. Not that you’re doing that at all, but I totally see why you might not want to talk business, especially if you’re in a field that people associate with monetary success.

I’m sure there are a million other things that you’re knowledgeable about that would make for awesome conversation. Besides, if people are really interested in getting to know you they’ll want to hear about all aspects of your life, not just you job.