#GoingBold :: Shana Dewitt: Coach, Designer and Podcaster

Bold & Pop: #GoingBold Feature with  Shana Dewitt: Coach, Designer and Podcaster
Bold & Pop: #GoingBold Feature with  Shana Dewitt: Coach, Designer and Podcaster

Tell us your bold boss story!: 

I am an entrepreneur with a dream and a vision just like you! After 5 years as an Art Director and Lead User Interface Designer for a fortune 100 company, I took my side hustle, Tipsy Studio, full-time. I traded in my glass office, heels, and commute for t-shirts and the sounds of my children. I spent the next four years building my own business and working with entrepreneurs to help them launch and grow their business. I practiced all of the marketing and design skills I used working for big companies and applied them to business for solopreneurs. You can find me most days working in my home office sans makeup just like this drinking Le Croix and talking shop with my business partner Josie.

Getting where I am today took some time and it wasn’t easy. I had to learn what it really meant to be an entrepreneur.

It’s letting feelings of being a fraud, not being good enough, and comparison hold you back. It’s trying to balance your life with the work you do and navigating stages of hustle and flow. It’s figuring out how to stabilize your income and do the work while wearing so many hats. Most importantly is knowing how to shift and change.

Being an entrepreneur is a journey with a winding road.

When I started my business, I offered branding and web design. That first year I worked with some amazing companies like Anthropologie and Pirouline. Then, I decided that I wanted to work with only creative entrepreneurs. I spent the next year perfecting my systems and processes. Along the way, I figured out my favorite clients were often not creatives. So, I shifted again to focus on just entrepreneurs. I started spending a lot of time actually coaching clients on marketing strategies and helping them stay positive and motivated during our work together. Once I realized how much I loved sharing what I know, I began speaking and teaching and later developed my own online courses. 

Finally, I had to face the facts. Design wasn’t the thing that really lit me up. Developing strategies, systems, and process to market and grow business that fit people’s unique vision is what I really love to do. Talking to entrepreneurs about who they are and how to build a business around their values and how they want to live is my passion. This is how I can truly help people.

So here we are!

Today, I help women create a business that stands out and supports the kind of life they want to have today. I have over 14 years of experience in creating brands for international companies and entrepreneurs. My process combines my tried and true methods, plus an intuitive approach, to get to the heart of your brand and your vision for your business.

We're all about bold boss moments, tell us about one of yours!: 

Leaving a solid job to start your own business is the boldest move you can make!

What advice or words of encouragement do you have for the Bold Boss Tribe?: 

Know that the journey you are own is it's own training to get to where you want to be. You have to lean into it and give yourself grace with the knowledge that everything that is happening is for you.

Website | Facebook | Instagram | Podcast Instagram

Have an awesome bold boss story of your own? We want to hear from you! Check out the dets and submit your story for consideration.

P.S. Exciting news! We launched a free #BoldBossTribe Facebook Group and would love for you to join us! Come on over!



3 Tips to Help you Crush your First (or Next) Public Speaking Gig

Bold & Pop : 3 Tips to Help you Crush your First (or Next) Public Speaking Gig

For the last two years, one of my yearly goals has been to try 5 new things or say yes to things that scare the crap out of me. So when I got invited to speak to a group of 100 wedding and event planning professionals in Seattle… I knew it definitely fit the bill! At first I was like OMG what an amazing opportunity to meet fellow biz owners and then a few seconds later I was like umm wait… how many people?! Umm that’s approximately 70 more people than I’ve ever spoke in front of and umm when was the last time I did a presentation like this.. oh college?!  Cue the feelings of self-doubt and wondering if I could actually pull it off. There is a reason that public speaking is one of the top fears of people… it’s scary to put yourself out there. Which is why after about 15 minutes of freaking out, I replied to the email with a big ol’ COUNT ME IN!

We all know those quotes about how growth is what happens when you push yourself out of your comfort zone and all of that jazz, right? Let’s be honest, while deep down we all know that. It’s a heck of a lot easier to repin those quotes on Pinterest than to actually live it. Which is exactly why I started making that yearly goal because it holds me accountable to say YES to opportunities like this that if I sat on for a few hours I may try and talk myself out of them. Here’s the thing too, if you don’t say yes to opportunities like this then you could miss out on something that you may end up being really passionate about. Plus, we have BIG goals at Bold & Pop sooo maybe it’s 100 people today… but maybe even 500 or more in the future! So now I’ve given you a little background on how this introverted leaning biz owner talked herself into saying yes to this opp, let’s talk about the prep that actually worked for me!

Do Some Research

When I decide to do something I go a little crazy and go all in on learning as much about it as I can. It may be a little excessive at times but… 🤷‍♀️So I started reading different articles and blog posts with tips for public speaking as well as creating presentations with impact. While this was my first big solo speaking gig… I should note, that I do have some speaking and media experience. I’ve been interviewed by top-tier media outlets including on air segments, spoke on panels, given client presentations and taught social media material before but this was a bit different so I dove right into specific tips on presentations. Two of the resources I liked the best were a webinar from Jess Ekstrom who is a motivational speaker. Her webinar was giving a pitch for her course, but it did give me a nice little boost that we allll have great material to share and some of the basics about speaking.

Then the resource that was the most helpful was the book, TED Talks : The Official TED Guide to Public Speaking. It may have over prepared me for my specific opportunity, but it was just a wealth of information. We’re all familiar with TED talks and the impact they have right? So what better resource to learn from! There was so much great information and a lot of detail about different ways to give presentations and carving out the method that works best for you. 

Put Together Your Presentation Early

Naturally this is the next step! When it comes to presentations I’ve always been a little bit of a nervous nelly. Hence, why this was a big deal for me! If you’re in a similar boat I recommend putting your presentation and plan together earlier rather than later. That way, you’ll have adequate time to prepare and honestly, just having a game plan for the big presentation relieved a lot of stress and reminded me, umm hiii Anna, you know your ish girl! Depending on your gig, the structure will probably be different. For mine, I was essentially teaching a class so having a powerpoint presentation was part of the plan and I wanted to make sure I had enough to guide my talk without writing a novel on each slide.

I had a pretty big chunk of time to prepare, nearly two months, so I was really able to space things out. I started by strictly just getting my outline done about a month and a half out just to nail down the material I’d be covering. Then about a month out I started putting together my first draft of my presentation (there were a lot of variations)! My rec is to put your ideas to paper as soon as you can and know you’re going to make edits along the way.

Practice, Practice, Practice

Onto the biggestttt part of the prep process, practicing! At the beginning I just started by running through my slides and seeing where there were gaps or where the flow needed to be revised. Cue adjusting the slides 10 million times 🙈haha, ok that’s a bit dramatic but after a few times you’ll notice what you want to adjust. Here are some other tips when it comes to practicing.

  1. Run through your presentation 10-15 times prior to giving it. Okay, I totally made this number up and since I legit looked this question up, I can tell you everyone has a different suggestion. Some people won’t need to do it that much (and others may want to do it more), totally up to you but that’s the range I gave myself to hit. My presentation was in the 35-45 min range so it was definitely a chunk of time but it really helped me feel confident. I gave the points a little different every time I ran through it but it just helped me get really comfortable with the material that by the time I gave the presentation I really had my talking points down.

  2. Record yourself! This is something that really helped me! I actually just flipped the video on my phone on and just recorded the audio although you could totally do the video too. What I did was record one of my sessions each day the week leading up to the presentation. Then, I when I went on my afternoon walks after work (gotta get those steps in after sitting all day!) I listened back to myself like I would a podcast. It felt a little weird to do at first, but you pick up on so many more things about how you could explain something better or try to cut back on filler words.

  3. Practice in front of someone. Ok so I actually didn’t do this one but I’m glad I did. Funny enough, I thought I’d be more comfortable doing my presentation in front of people I didn’t know than those I did. I know.. it’s silly. This ended up being really helpful though. Even better if you have someone in your life who is unfamiliar with the content so you can ask them if there are any parts you could explain more thoroughly and if your material makes sense for a beginner on the subject.

Set Expectations and Work on your Mindset

Last but not least, I think getting in the right mindset is SO important. Mindset in general has been something I’ve been really focused on the last year but it was especially important in this case because hiii I was doing something I was really nervous about! So here’s a rundown of a few exercises and things I did. If you haven’t done mindset work before some of these may sound kind of weird, and when I learned about them in books I was like.. ummm yeah I don’t think I could do that, butttt after giving a few a shot they’ve helped so I decided to add them to my prep.

  1. Positive affirmations. If you tell yourself you’re awesome enough times, you’ll start to believe it! So in the weeks leading up to the event I wrote across the top and bottom margins of my planner that “I am an awesome speaker and was going to give a bomb ass presentation” because obvi that’s what awesome speakers tell themselves right?! Haha, maybe you’ll be more elegant with your phrasing but reading that every day helped me think of all of the things that were going to go right and not vice versa!

  2. Manifesting. Another thing I did was visualize and embrace the feelings I was going to have after I crushed my presentation. By focusing on that, I was able to push away any negative thoughts because I was so focused on crushingggg it!

  3. Set expectations. What are your goals for your presentation? Other than getting through it? Setting expectations can help you stay focused on the things that actually matter to you. For mine, I acknowledged that hey, this is my first big presentation.. it may not be perfect and I’m guilty of stumbling over my words sometimes but I decided that stuff didn’t matter to me as much. I decided my goals were to show up, bring serious value, and teach everyone there new strategies they could implement in their businesses that would made a real. And guess what, if I did all of that, chances are none of the attendees were going to notice too much if I made a few goofs here or there. There are a million things you could focus on for your presentation so find what means the most to you.

So there you have it! All of my pre-speaking gig advice to help you become the next Tony Robbins! Haha, ok maybe I wouldn’t go thatttt far, but then again you never know! And in case you’re wondering, my presentation went off without a hitch and even better than I thought it was going to! I bet yours is going to do the same too!

P.S. Exciting news! We launched the free #GoingBold Facebook Group and would love for you to join us! Come on over!



#GoingBold :: Shelly Jackson and Callie Cullum of The Look & The Feel

Bold & Pop :: #GoingBold Feature with Shelly Jackson and Callie Cullum of The Look & The Feel
Bold & Pop :: #GoingBold Feature with Shelly Jackson and Callie Cullum of The Look & The Feel

Our names are Shelly Jackson and Callie Cullum and we run a full-service branding studio called The Look & The Feel based in Atlanta, GA and San Diego, CA. At our business, we provide design, coaching, content, and strategy for creative and adventurous business owners and organizations.

We started The Look & The Feel because we believe that both branding and running a business should be fun, rewarding, challenging, and inspiring. Drawing from our personal experiences starting our own company, we aim to help other entrepreneurs feel proud of their brand, inspired by their story, and confident in their work.

We've been working together since 2013 when we first met in the San Francisco Bay Area while working at an arts nonprofit. We came together in early 2017 to establish The Look & The Feel, after we realized that, with our powers combined, we could provide more robust branding, design, and strategy services to businesses.

After living with chronic pain from spinal injuries (that's a story for ya!) we both were eager to start our own businesses and work for ourselves so that we can prioritize our own care and wellness. Now, we work with other emerging and established entrepreneurs to help them feel more confident, capable, and happy doing the work they put out into the world.

Bold & Pop :: #GoingBold Feature with Shelly Jackson and Callie Cullum of The Look & The Feel

We're all about bold boss moments, tell us about one of yours!: 

Something interesting, and conversation-worthy, is how we both broke our spines when we were younger. Yeah, I know—totally bizarre! Living with chronic pain has taught us how to prioritize caring for ourselves, and it’s compelled us to be more aware of how we choose to spend our time and energy. We’ve realized that we can work for ourselves and that the work is hard, but we have the freedom to choose how we work and in what way. This lesson is the best gift we’ve gained from being entrepreneurs, and it’s at the core of the work we bring into the world.

What advice or words of encouragement do you have for the #GoingBold community?: 

Our shared experiences of living with chronic pain for much of our lives have taught us that, more than anything, you have to value and honor your own personal wellbeing because you're the only one who is responsible for your own self-care.

P.S. The Look & The Feel ladies have a special free downloads for you:

Shelly and Callie put together two freebies that they think will be helpful for your business too! If you’re looking to align your brand voice and visuals this one is for you! Or if you’re looking to feel better about the work you’re doing then this one may be for you.

Website | Facebook | Instagram | Pinterest

Have an awesome bold boss story of your own? We want to hear from you! Check out the dets and submit your story for consideration.

P.S. Exciting news! We launched the free #GoingBold Facebook Group and would love for you to join us! Come on over!