Home » Interviews » Not Asking for Help With This Might Be Holding You Back (According to Carrie Smith) [TDI052]

Not Asking for Help With This Might Be Holding You Back (According to Carrie Smith) [TDI052]


One of the things that seems to really plague an entrepreneur’s growth is failing to ask for help when needed.  For today’s guest, Carrie Smith, this was a big breakthrough that really helped take her online business to the next level.

Carrie’s story starts out like many others – she worked as an accountant, in a job where she gradually became less and less happy over time.  She eventually broke free to pursue her blog (Careful Cents), among other projects, full time.  It hasn’t even been a year since she quit her accounting job, and she’s already making just as much as she did when she was employed.

In this interview, Carrie talks about some of her achievements, including how she’s been successful as a freelance blogger writing for many well-known online publications.  More importantly, she discusses how asking for help really allowed her to grow her business and live a more relaxed lifestyle.

Enjoy the interview!

Carrie, I really enjoy your site, Careful Cents. I like the stories you’ve featured of people who are on their way to quitting their day jobs, as well as the various personal finance and organization tips you’ve shared.

Tell us a bit about your background and journey – How did you go from small business accountant to entrepreneur/blogger? What are you most focused on today in your online business?

I actually never thought I would be a full-time entrepreneur. I started my blog as a side-gig while I was working as a small business accountant for an oil and gas company here in Texas. But as my job started going down a different path, and I noticed how frustrated and unhappy I was, I knew I had to pursue a different career.

I wanted more freedom, and not to be known as the “workaholic career woman,” so I started working at H&R Block during nights and weekends to try something new. I wanted more interaction with entrepreneurs and small businesses, to help them find freedom through getting their finances organized. That desire to reach more people, and share the out-of-the-box ideas I have regarding finances and organization, led to starting my blog in the summer of 2011.

As a fun side note, my business name came out of my own personality (a very careful and calculative person) and the letter “C” which correlates with my first name!

What has been your greatest success (or successes) so far with your online business?

My greatest success so far is something that doesn’t even have income attached to it, and that’s my private club of freelancers and solo business owners. I started the group as a community gathering place for entrepreneurs, like me, who needed support but were also trying to learn the ropes of running a virtual freedom business.

Now the group has grown to over 350+ members and many of them have landed big-time jobs because of the connections made (one of the writers was even published in a Kindle book). It’s a completely free group, and I love every minute I get to interact with other go-getters. In fact, many of the success stories I feature on the site come from freelancers that are members of this group.

I will also add that I’m extremely proud of myself for hitting a $5,000 monthly revenue milestone which equates to making more income from my online ventures than I did at my accounting job. Which is quite a feat, considering I still work about the same amount of hours every week (35-40).

Yes, I still have to pay my own taxes and insurance, but it’s nice to know that I haven’t even been self-employed for a whole year and I’ve been able to build this awesome community, while still being able to pay the bills.

Every entrepreneur experiences failure, but good entrepreneurs turn failures into building blocks for the future. What has been your biggest failure to date with your business, and what have you learned from it?

Oh gosh, this one has been a big one for me! I am a control freak who wants to do everything myself and no one else can do it better than me (can you relate?). But that was a big mistake on my part and one that quickly taught me a valuable lesson.

After months of trying to do it on my own, I had worked myself to the point of being physically sick. I was so stressed out I couldn’t sleep well and still hadn’t been able to increase my income.

I finally came to the realization that I’m not going to be perfect at everything, and there are tons of other entrepreneurs out there who can do it much better than me. I learned to humble myself and ask for help. Within two months I hired my first VA and actually took the weekend off (my first in about 6 months). Additionally I hired a business coach to help me stay on track going forward.

I see you’ve worked as a freelance blogger for a number of very well-respected websites, including Huffington Post and Yahoo! Finance. For someone who is relatively new to freelance writing, what advice would you offer to help that person get to “the next level” and actually secure opportunities to write for some of the larger online publications out there? (To what do you attribute your success in this area?)

Contrary to popular advice, I only blog on my own site 2-3 times a month and I focus most of my writing efforts for other sites and blogging projects. I would highly recommend this for any new freelance writer starting out. You’ll get way more exposure and gain valuable contacts by focusing your time writing for other well-established communities, versus blogging on your newer site.

This is a theory taught by Derek Halpern of Social Triggers, and since having put his advice into practice I’ve tripled my traffic in the past year. He even featured my successful case study at a Financial Media conference last year in front of hundreds of bloggers.

Essentially, you only want to blog if you have something of value to say or teach others. Or else you’re just adding to the noise of the blogosphere, and that’s no way to build a good freelance writing portfolio.

I know you’re big on using systems and organizational tactics to help entrepreneurs run their businesses better. What are a few of the most common suggestions you’ve given to the entrepreneurs with whom you’ve worked?

I always tell entrepreneurs not to be afraid to ask for help — based on my own experience of course. Whether that’s finding a mentor, hiring a Virtual Assistant or taking a class to learn how to DIY something. It will be the best money and time you’ve spent and you’ll come away with a much more efficient process of doing things, which will repay you in extra time and more money.

On top of that advice, I would highly recommend embracing all things digital. It’s SO much easier to communicate with your team, check your bank accounts and see how your business is doing, virtually. You’ll have more freedom and won’t be chained to your desk all day.

It may sound cliche, but “there’s an app for that” so whether that’s for budgeting your money or listing out your to-do’s, you should start utilizing mobile apps and online tools right now!

Let’s take a step back and look more generally at becoming an entrepreneur: If you had to take your best advice or inspirational thought and put it into one sentence or phrase, what would that be?

This is something I remind myself with my own pursuits, as well as my team who works with me everyday.

Skills can be taught, but character can not. What you do is more important than how you do it. [Click here to tweet this]


As long as I have the drive and hustle, and remember to embrace my morals, I can learn anything and everything. I can take business classes and read all the books in the world, but if I lose my self respect or let money corrupt my thinking, then I’ve failed.

What are your favorite online resources?

I would be absolutely LOST without Dropbox, which is awesome for file-sharing with team members as well as accessing documents and spreadsheets on multiple devices. I also live and die by Google Calendar which I use in conjunction with Asana (a free task management app).

And if you need some musical motivation for creativity, I am in love with Focus@Will which creates music that’s scientifically proven to make you more productive.

Lastly, all my financial accounts are synced to Mint.com which I check on a daily basis. My brain would not function without all of these tools!

Finally, where can people find you online?

The best place to connect with me (in real time) is on Twitter @carefulcents or on my website, CarefulCents.com. I also enjoy answering emails and hearing other freedom stories from go-getters via carefulcents@gmail.com, so feel free to shoot me any questions or comments.

Thanks so much for taking the time to do this interview, Carrie!

What did you think about this interview? Leave a comment below!

(Also, if you enjoyed this interview, like us on Facebook, and stay in touch with every new interview we publish. Thanks! 🙂 )

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