How to Be a Successful Blogger: Tips, Resources and Questions Answered

Editor’s Note: After receiving multiple requests for details about the images in this post I decided to provide links to the original post for each photo. In order from top to bottom (not including above image): 1, 2, 3, 4, 5, 6.

With the launch of my brand spanking new website and re-design I thought it was the perfect time to answer your questions and share some tips on the business of blogging. Before we dive into it, I want to give a shout-out to the fabulous women that made my vision a reality. If you are a blogger and looking for help with your site or branding I can’t say enough good things about all three of these women. The overall branding and design was executed by the insanely talented Eva Black. Eva is so easy to work with and as soon as we started talking about my new branding and site design she just got it. I love every detail she created and I think it embodies my brand beautifully. The site development (all the coding and behind the scenes work that is absolutely terrifying to me) was done by Rachel Rianne. Rachel not only figured out and implemented all the special functionalities I wanted for the site, but she made everything on the backend SO easy for me to use. For those of you who use WordPress, I’m sure you understand how terrifying it can be when you have a site designed and then you have no idea how to change or fix anything on your own. And last but not least, my beautiful new email templates were created by the amazingly talented Victoria McGinley. They are seriously gorgeous and so user-friendly. If you want to see for yourself sign up for my weekly newsletter Long Story Short which will be delivered on Fridays. So, back to the business of blogging, let’s dive in.

I’m going to break up this post into a few different sections. The questions I received from you guys were a bit all over the map and I want to address all of them, but some I’m better suited to answer than others so here’s the plan. First, I’ve answered a few key questions and provided what I think are the most important tips for success (more on that in a minute). Next, I’ve outlined some FAQ that cover more of the basics of blogging and finally, I’ve created a list of resources that include my favorite apps and other tools I use regularly.

Jess Ann Kirby wearing a Barbour Jacket in Newport, RI

Defining Success

First, let’s talk about defining success. It means different things to everyone. In all honesty I feel a bit silly talking about “how to be successful” when I don’t feel like I’ve achieved even half of what I want to accomplish. I guess for me there is no end point where I feel like if I do this or get that I’ll be successful, but I continue to set goals for myself and work towards my vision for my brand and business. It’s important to think about what success means to you because it will help you clarify your vision. Whether you want to be a full time blogger, do it as a side hustle or it’s simply a hobby, thinking about your idea of success is a really important first step.

The Why

You need to be able to answer the question, “Why Do You Want to Start a Blog?” I am sure there’s a lot of different opinions on this, but here’s mine. If you’re only in it for the money or free stuff you’re doing it for the wrong reasons. How blogging looks and how it actually is are two very different things. I’ve had this conversation with a few close friends that are also full time bloggers. I think the blogging industry as a whole often masks the reality of having a full time blog. I guess part of what’s alluring about blogging is the illusion that it’s all glamorous perks and free stuff. There are definitely incredible benefits and I LOVE my job, but it’s not for everyone. I wasn’t able to survive off of my blog until somewhat recently (that’s 3 years of working non-stop and for some it takes longer than that). I work really long hours and a lot of the day to day responsibilities are anything but glamorous. That said, I love it and can’t imagine doing anything else, but you have to be realistic about what kind of time, money and energy you’re willing to commit.

Establishing Your Brand

Now more than ever, it’s crucial to be clear about defining your brand. It’s a very crowded market and there are so many blogs out there, you have to be able to offer something unique and useful to your readers and followers. I’ve come up with a few questions and tips to help you define your brand and voice.

Be authentic – Duh. I know, this probably seems super obvious but it’s the single most important thing in defining your brand. Authenticity and staying true to yourself will take you far not only in blogging but in life. I’m very deliberate about the collaborations and companies I associate myself with. I say no almost as often as I say yes to opportunities. If it doesn’t feel right or it’s not a product or brand I genuinely like, I won’t put it on my blog.

Find your niche – There’s no sense in trying to do and be everything. Hone in on what sets you apart. What unique perspective or skills do you have to offer? What are your passions? Think about what you love and what excites you and the ideas will start to flow.

Use What You’ve Got – For me, one of my “aha” moments was moving back to Newport. I started the blog while I was living in NYC because I needed a creative outlet and I wanted to try and get a job in fashion. When I moved back to Newport, I realized what a unique opportunity I had being able to share my take on personal style with my hometown as the backdrop. It kickstarted my brainstorming and creative process and everything took off from there.

Quality over Quantity – It’s really important to be critical of oneself and seek (constructive) criticism from others. Be honest and realistic with yourself about your content and at the same time don’t let it completely hinder you from putting content out there. Everybody has to start somewhere, I cringe at basically everything I did in the beginning, but it’s all a part of the process. On that same note, focus on quality and consistency. If you only have time for 1 blog post per week, focus on making it a really good one. For my style posts, I don’t ever shoot more than one look in a day, for me it doesn’t feel authentic. That’s not necessarily realistic for everyone but my point is I’d rather have 3 really good outfit posts consistently than posting everyday and sacrificing quality. I approach all of the content on my site this way.
Another really important point regarding the above, the same goes for your following. Engagement is so much more important than the number of followers you have. So many people buy followers now which is something you should NEVER do. A smaller-midsize blogger with great engagement can have the same if not stronger impact than someone with hundreds of thousands of followers but little engagement. For brands, an engaged and enthusiastic audience is incredibly valuable.

Promoting Your Content

So you have a blog and you’re publishing content. Now the question is, how do you get your content seen? Aside from the obvious things like promoting it on social media here’s a few things that have worked well for me:

Create content that people want to share – Particularly when it comes to imagery if you have beautiful photos they’re more likely to be shared by others. I make sure to tag any brands I’m wearing in any social media posts and if I’m working with a brand or have worked with them in the past I often take some time to send them links to posts and let them know they can use any of my imagery on their own social media channels (with credit of course).

Partner with other bloggers – Whether it’s a just a simple shoutout on Twitter or a style post partnering with another blogger, this is a great way to get in front of a new audience that’s already familiar with and probably more enthusiastic about following blogs.

Emails, emails, emails – Growing your email list should be a main priority. Make sure the content you’re sharing via email is helpful/useful to your readers and provides something that they can’t get elsewhere.

Focus on the channels that work – I play around with where I share my content but I tend to focus on the places where I get the most return. Pinterest is a big traffic driver for me so I dedicate a decent amount of time to it. The same goes for Instagram for me. Pay attention to your analytics and leverage the channels that drive the most traffic and engagement for you.

SEO – Search Engine Optimization. Three words that can sound a little bit terrifying. I didn’t pay much attention to it when I first started blogging and I wish that I did. It’s incredibly important and a major tool in helping you grow. With the help of Chloe Digital and doing a ton of research on my own I feel like I have a pretty good grasp on it now. Check out this SEO section on Thrifts and Threads as well as the Chloe Digital blog, both have a ton of helpful info.

Working With Brands

Now we’re getting to the good stuff. Other than “How Do You Make Money” I think this is the question I get more than anything, “How Do You Work With Brands?” Truth be told there are a lot of different ways to partner with brands. If we go back to the very beginning the main things I focused on were events and networking, getting the attention of brands by wearing their clothes and tagging them, and outreach. I’m a major introvert so going to events by myself was absolutely terrifying but I forced myself to do it and I’m so glad I did. I met people that I still call friends (brands, bloggers, PR reps etc.). I do less of this now but it’s important to always put yourself out there and meet people. When I first started no one knew I existed (and my content was embarrassingly below average) so there weren’t any brands knocking down my door to work with me. That said I consistently wore pieces from my favorite brands and would tag them on social media. After about a year I started reaching out to certain brands (look for the PR/Social contact on their website or send them a DM on Instagram), trust me there were plenty that never responded, but some did. And I STILL work with those brands to this day. When reaching out to a brand keep it short and sweet. Introduce yourself, a little about your blog and your audience and why you want to work with them/why they’re a good fit. Do not email a brand and ask for money. Yuck, gross, ew (more about monetization below). A few more things about working with brands and building relationships:

Over Deliver – If you’re working with a brand (paid or not) go above and beyond. Be responsive in your correspondence, go the extra mile in the content you create for them. When I have a collaboration with a brand I always do a little extra beyond the scope of the contract. It’s a nice way to foster a strong relationship, they have a ton of people to choose from and they chose you! Make it worth their while.

Set Clear Expectations – Making sure you are both on the same page in terms of the outcomes of the collaboration is crucial. Put it in writing from the start. Everyone will be happier when you know what they expect from you and vice versa. On that same note make sure you’re comfortable with the agreement. It’s ok to negotiate, I was terrible at this in the beginning, it’s really hard, particularly when you’re doing it on your own behalf but that’s the nature of being your own boss.

Don’t Be a Jerk – It’s a very small world. If you’re a pain in the ass, people will find out, word will spread like wildfire and you’ll be hard pressed to find brands that want to work with you. Your reputation is EVERYTHING in this business, and with a bajillion bloggers out there, it’s so important to have a good one. If you’re easy to work with, a nice person, and consistently over-deliver, brands will take note. This is a business, and acting in a professional and respectful manner will take you a long way.


“How do you make money blogging?” The question that literally everyone wants the answer to. The reality is there are a ton of different ways to monetize your blog. The other reality is that not everything is as it seems. Just because it looks like someone is making a ton of money from their blog doesn’t mean they actually are. I only say this to point out that you can’t get caught up in what everyone else is doing, focus on you, what you’re good at and what you want to accomplish. You have no idea how another blogger got that collaboration or that trip or that expensive bag, and it doesn’t matter, you gotta do you boo. Here’s a few ways you can monetize your content:

Affiliate Links – There are a bunch of different networks out there now for affiliate linking. I work with rewardStyle and I have friends that work with ShopStyle. rewardStyle is pay per purchase and ShopStyle is pay per click, you can experiment with both and see what has a better return for you.

Ads – There’s tons of ad networks out there that pay based on impressions. So you put an ad(s) on your site and you get paid based on the number of impressions that ad gets (this depends on your traffic). I personally don’t like the look of ads on my site so I don’t do this but I see tons of blogs with them and they don’t bother me, it’s personal preference really.

Sponsored Content/Collaborations – Most of my collaborations now come to me vs. me reaching out to brands but I did at one point do a lot of outreach. Again this wasn’t until I had established a relationship with a brand and would pitch them an idea/concept with what I would do and the budget. Pricing in this industry is all over the place and it can be hard to know what to charge. Again this is where you need to be realistic about your content and your audience. If you just started out and have a small following focus on creating good content and building relationships not charging money for partnerships. If a brand approaches you and asks for your rates you can a) send them your media kit or b) ask them what their budget is. This is a good way to get a feel for where they are. Again it’s important to be very clear about what the brand gets for your fee, be specific about what your fees include (social coverage, their use of your imagery and where,  etc.). Blair shares some advice for what to charge that’s worth checking out.

Editor’s Note: After receiving multiple requests for details about the images in this post I decided to provide links to the original post for each photo. In order from top to bottom (not including first image): 1, 2, 3, 4, 5, 6.


1. Who shoots your photos? My boyfriend Craig shoots 99% of all my photography. Photographer credit is at the beginning of each post.

2. What camera do you use? When we first started we used a Canon Rebel t3i. About a year later we upgraded to the Canon 6D which is a really great full frame camera and I highly recommend based on quality and price (and the kit lens is great). We then upgraded to the Canon 5D Mark III and most recently switched over to the Sony a7II which is a mirrorless full frame camera. Typically Craig shoots with a 50mm (good for full body and close-ups), 35mm (good when you want to incorporate the background), or 23mm (wide angle) lens. An 85mm and a telephoto are both on our wish list right now. We also have a GoPro and a Drone for video.

3. How do you edit your photos? I use Lightroom to edit all of my photos. I know many bloggers use Photoshop. I think Lightroom is easier to use and I like the workflow. For Instagram I put all of my photos through a VSCO filter but usually at a very slight intensity so it doesn’t alter the image that much but makes my feed cohesive.

4. How do I start a blog? I’m not going to go into detail on this because I think there’s already a ton of helpful info out there on this topic. I recommend checking out Thrifts and Threads by Brittany Xavier, she posts a ton of content about blogging. I’ve also included a bunch of links to helpful sites in the resources section below.

5. Do you consult with/mentor bloggers? I wish I could but I don’t have the time. I highly recommend Chloe Digital and Victoria McGinley.

6. Where do you find inspiration? Honestly everywhere. Pinterest, movies, nature, travel, magazines, if you can allow yourself to be vulnerable and open to experience the world around you, you can find inspiration almost anywhere.

7. Can we meet up? My schedule is jam packed every day. I also do a lot of work travel so in my free time I just want to unplug and turn off my “work brain.” It’s nothing personal but I have to reserve what little free time I have for myself. Occasionally I do events though so please come to those!

Blogging Resources


Lightroom – I recommend getting an Adobe Creative Cloud Plan, they’re inexpensive and give you access to as many Adobe products as you want.
VSCO – I use a few different filter packs on my iPhone but most frequently I use the analog or hypebeast presets.
Color Story – I don’t use this as much but it’s great for brightening certain types of photos or making edits you can’t do within VSCO.


Tailwind – Great Pinterest scheduling tool
Planoly – For planning Instagram
UNUM – For planning Instagram (I don’t use this but I think it’s the same as Planoly but free)
Dropbox – Great for file sharing, storing imagery, etc.
Google Sheets – I use this track collaborations and plan my editorial calendar.
Hootsuite – Great for scheduling Twitter posts
PayPal – Good for invoicing and receiving payments (see below)
Quickbooks – Just switched over to this to manage my financials and accounting since I set up an LLC

Additional Resources

Chloe Digital – They have multiple plans depending on your needs. Very helpful for WordPress users and planning/strategy needs. 
Victoria McGinley – Branding, Site Design, Email Templates, Media Kits
Eva Black – Branding, Site Design, Media Kits, Custom Typeface + Lettering
Leap by Blair Staky – Great resources and blogging tips


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  1. Stephanie wrote:

    I’m a new blogger, so this post was super informative! Love your new website, and thank you for the great tips and post!

    1.17.17 | Reply
    • Jessica wrote:

      Thanks Stephanie! So glad this was helpful. xx

      1.17.17 | Reply
    • Jen wrote:

      Thank you for taking the time to put this resource together, Jess! Super informative, inspiring, and fresh. Keep doing you. 🙂 xx

      Jen | affecionada

      1.17.17 | Reply
  2. Katrina wrote:

    This was such a great post and I learned so much from your awesome tips! One question, what lens do you find works the best for full body/full outfit photos?

    1.17.17 | Reply
    • Jessica wrote:

      Hi Katrina, thanks and I’m glad this post is helpful. For outfit shots we typically use a 50mm 1.4 lens. If we’re traveling we might use a 35mm because it’s a little more versatile for getting the background/locations in the photo.

      1.17.17 | Reply
  3. Marta wrote:

    I’ve been blogging for a little bit over a year now and this was extremely helpful! I still don’t feel 100% comfortable contacting brands myself because I’m not sure if I can offer them what they want. But I’ll definitely work on it!

    1.17.17 | Reply
    • Jessica wrote:

      So glad this was helpful Marta! Best of luck with your blog. xx

      1.17.17 | Reply
  4. Diana wrote:

    Thank you!! Your information is extremely detailed and helpful.

    || D I A N A ||

    1.17.17 | Reply
  5. This post is awesome, Jess! Congrats on your new site (it’s ah-maze-ing) and all your success. It’s so inspiring to see a fellow Rhode Islander killing it in the fashion blogging world!

    Can I ask how you’re liking your new mirrorless camera? I’ve been doing some research and would like to get one myself but I haven’t decided on a model yet.

    xx Becky

    1.17.17 | Reply
    • Jessica wrote:

      Thanks Becky! Craig really loves the mirrorless, we use it for all photos and video now. It’s incredibly lightweight and I love the image quality.

      1.17.17 | Reply
  6. Casey wrote:

    First of all, loving the new format of your website! I have been blogging for a while but I have most recently really found my niche, and this post was incredibly helpful to help me plan my next steps! Thank you for this!

    1.17.17 | Reply
    • Jessica wrote:

      Thank you so much Casey. So glad it was helpful to you. xx

      1.17.17 | Reply
  7. Cat wrote:

    Great post! It was very informative! I just relaunched my blog… 🙂

    Cat //

    1.17.17 | Reply
  8. Julie wrote:

    Thank you so much Jess for this mega useful post. You know, when you start as a tiny blogger, the blogosphere seems oh so daunting and finding the right tools and the right approach is challenging at times. Although I feel I have learnt lots by simply reading posts and following a number of bloggers your post makes it clear, neat and gather all the most important bits one should need to pursue their blog dream. Thanks for keeping me inspired! Julie xx

    1.19.17 | Reply
  9. Kate wrote:

    Thanks so much for blogging about this topic. I can tell that you put a lot of time and effort into this post! I’ve been blogging for over three years but predominantly as a creative outlet. I really appreciate your advice on working with brands and monetization now that I’m looking to eventually take it to the next level.

    Taffeta & Tulips

    1.19.17 | Reply
  10. Thank you so so much. There is so much to learn. We need more people like you who are willing to share their journey and what it takes to achieve success. #TakingNotes <3

    1.20.17 | Reply
    • Jessica wrote:

      I’m so glad it was helpful. Thanks for reading! xx

      1.20.17 | Reply
    • Jessica wrote:

      You’re so welcome Hannah. I’m so glad it was a helpful post. Thanks for taking the time to check it out. xx

      1.20.17 | Reply
  11. Kylen wrote:

    WOW. This is an amazing resource for blogging. Thanks for taking the time to set up all these helpful details.

    XO Kylen | Kylen Every Wear

    1.20.17 | Reply
    • Jessica wrote:

      I’m so glad it’s helpful Kylen. Thanks for reading. xx

      1.20.17 | Reply
  12. Janelle wrote:

    Hi Jessica,

    This post was awesome. I am loving the new website and the new name.
    I definitely agree with you about not buying followers etc. but what about when you are organically growing your following via all of your social channels, but you see people blatantly buying followers, yet they still are receiving brand deals…….

    I’d appreciate your thoughts on that.



    1.20.17 | Reply
    • Jessica wrote:

      Thanks Janelle, I’m so glad you found the post helpful. Honestly re: buying followers, I have a few thoughts. The first is that it’s just wrong, from a moral and business perspective. It’s cheating and for those people that do it, they’re the ones that have to live with themselves. I think some brands are slower to catch on than others and quite frankly it can be hard to discern between people with real and fake followers because some people also buy likes. The reality is though, if you’re buying followers and likes, you’re not going to get the same return for a brand as someone with genuine followers that are actually engaging with their content because they like it. I would think most brands, when measuring the performance of a campaign after the fact, would realize the person gave them little to no return on their investment. I think ultimately it will catch up to the people that are faking it by buying followers and likes. Either way, in every aspect of my business, the ultimate test is “can I be proud of this decision?” If the answer is no, then it’s probably not a good one.

      Hope this helps answer your question. xx Jess

      1.21.17 | Reply
  13. Sheila Joy wrote:

    Thank you for this post! I have some blogging goals I’d like to achieve this year so I will definitely be referencing this post 🙂

    P.S. – Love your blog design!

    1.23.17 | Reply
    • Jessica wrote:

      Thanks Sheila! So glad it was helpful. xx

      1.23.17 | Reply
  14. Kateri wrote:

    Thanks so much for putting this together! I’ve found it very helpful. Can I ask? Do you use an WP plugin for showing Instagram, and if so, which do you use?

    2.13.17 | Reply
    • Jessica wrote:

      Thanks Kate. I had my site custom designed but it looks like the plugin my designer used is called Instagram Feed Pro Developer. It’s a WP plugin.

      2.13.17 | Reply
  15. Erinn wrote:

    Jess, this is incredible. Thank you for sharing all your wisdom. I’m a very fresh blogger, but all this information is SO helpful for me to figure out what my goals are.

    You are so great!!

    2.15.17 | Reply
    • Jessica wrote:

      I’m so glad it’s helpful! Thanks Erinn.

      2.17.17 | Reply
  16. Johanna wrote:

    Thanks a lot for sharing some of the tips especially as a beginner it is good, to have many advices gathered.

    2.17.17 | Reply
  17. Felicia wrote:

    Thank you for your wonderful insight! I am a new reader of yours, but I’ve been following you on Instagram for a while. I’ve also been blogging for over a year now. So any advice that I can get about improving my hobby that has become a side-hustle is great!

    5.30.17 | Reply
    • Jessica wrote:

      Hi Felicia, thanks so much for your comment. I hope some of my tips are helpful for you! xx

      5.31.17 | Reply
  18. Thanks for these tips! Super helpful 🙂

    12.17.17 | Reply
  19. Thank you so much for taking the time to share all of this! After taking a break from writing, I’m in the midst of a relaunch and getting back in the groove. There’s so much to think about beyond writing and your guidance is uber thoughtful. Love the blog!

    1.1.18 | Reply
  20. Zaida wrote:

    Starting my blog this year and this post has definitely been the most useful so far. Thank you sharing! Hope to hear some updates on this in the future. Enjoy seeing your work.

    1.3.18 | Reply

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