31 Things Boss Ladies Wish they Invested in Earlier in their Businesses

May 24, 2017
Aleia Walker | boss ladies invest | invest in early businesss

When I first started learning web development, I thought it would be a catalyst to get me out of a job I hated and to another full-time job. I thought starting a business was “too hard” and I shied away from the challenge. I took on freelance clients but charged this is extra income rates instead of I need to make a living rates. I treated my business as a hobby and I wish had invested time in asking similar business owners how to run a business.

My tribe – which includes my coach, business besties, fellow freelancers, etc. – are the ones who’ve helped me figure out what I needed to know (and what I didn’t know that I didn’t know) the quickest. They’ve helped change my mindset, workflows, confidence and #allthethings ( <- get use to seeing this phrase) that would have taken me 10X as long to change alone in my little bubble.

But I know that I’m not the only business owner that feels they waited too long to do something in their business.  And I wanted to know what the influencers in the online business world wish they had done sooner.

So I asked.

Below you’ll find the words of a ton of boss ladies who are killing the game now but think back to when they started and wish they had done XYZ thing different. You’ll find some similarities but they are definitely bits that ring very similar to their individual UVPs (unique value propositions) – which shows just how passionate they are about what they do now.

So check out these  boss ladies, their insights, and their businesses.

Boss ladies wish they had…

Don't Work Alone, Find your Tribe


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…hired help sooner.

1. One thing I’d wish I’d done sooner is hire help. It seems like a big investment but it’s worthwhile because it’s going to save you time and stress so you can focus on the most important areas of your business!
Nesha Woolery of

2. Hire help! I wish I had started outsourcing more in my business even earlier. Every time I go on a hiring binge, I get scared out of my mind, but the extra costs are soon covered by the investment. It’s scary at first, but well worth the sanity and profit it puts back in your life!
Christina Scalera of

3. Hiring an assistant. I was so scared to do it, but it helped me feel like I wasn’t doing it all alone.

Niamh Arthur of

4. I would say the once thing I wish I did sooner in my business would be to outsource. Trying to do everything myself was just holding me back and making me feel overwhelmed. Having a team of people who help me now allows me to focus on my expertise and do what I love!

Alli Elmunzer of Turquoise & Palm

…started putting themselves out there earlier

5. I wish I would have gotten out of my own head and started being visible online sooner. I spent the first 3-4 years of my business in a fog of babies (my own, ha) and business without taking the time to “get out there” and get to know other business owners. Once I did that, things started clicking and my business skyrocketed.

Jessica Stansberry of Hey Jessica

6. One thing I wish I would have done sooner is taken it more seriously. I started my blog as a hobby and didn’t even invest in a domain name in the beginning. I should have bought the domain right away, started on WordPress, and had a professional design.

Michelle Schroeder-Gardner of Making Sense of Cents

7. I wish I would have been more proactive, sooner. I think for a long time, especially when you’re just starting, you don’t feel confident in promoting your work because you’re waiting for a milestone to validate what you can bring to the table. I wish I would’ve not waited for that.

Vivian Nunez of
Take a peek at her Instagram

8. The easiest answer to what I’d wish I’d done sooner to in my business, would simply have been to have started sooner. Believing that I would be successful was difficult, almost impossible. When I finally set my mind to it, opportunities opened right up, almost immediately. It’s about believing in ourselves, and having the discipline to keep growing.

Peggy Dean of The Pigeon Letters

9. Booked myself out for 6 months before going full-time with my business.

Halley Gray of Evolve and Succeed 

10. I always thought there’s a perfect time for everything that comes our way. But, when it comes to online businesses or the competitive markets I have to admit that one should always make fast decisions.

I wished to have developed a killer content strategy and a rocking marketing plan for my online blog. This is the one thing I wished to have started even before starting my blog. With growing time, I realize how significant it is to develop strategies for surviving online.

Arfa Nazeer of Epife

Interested in free courses for online bloggers? She’s compiled a list here

…invested in building their brands earlier.

11. Sitting down and defining the purpose and goals of my business – defining my brand. I didn’t initially really know what ultimate value I was offering clients, and that kept me from marketing successfully and from having a focused service to offer.

Hannah Beasley of Hannah Rose Creative

12. If I could go back, I would have invested in professional brand photography and headshots that speak to who I am as a copywriter and content creator. It’s been one of the biggest game changers in my business! They look beautiful on my website and I can repurpose them to use on my social media channels. It’s an investment worth making in every way!
Kayla Hollatz of

13. I wish I had invested in a fully functional membership site when I first launched the Styled Stock Society last year! I originally launched using a subscription program that was limited in its capabilities and didn’t have all the things I needed to scale the membership in the future. By the time I upgraded to a fully functional membership platform, I had over 450 members and (somewhat of) a logistical nightmare! Had I taken the time and made the investment in a real membership site from the beginning, I would have saved a lot of time (and headaches) in the long run!

Elle Drouin of Wonderfelle

14. Just one thing, lol? That would probably have to be investing in branding and website.

Stephanie Thacker of Steadfast Bookkeeping

15. Professional head shots & branded photos to use on my website and social media. They also gave me the confidence to believe more in myself and my business which translated into more clients feeling the same way.

AllieDanae of The Social Walker

Don't Work Alone, Find your Tribe

You're new to the freelancing game and struggling with working alone in a bubble. But you don't have to, you just have to know where to look for others like you.

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…invested in a coach and/or building their tribes earlier.

16. I wish I invested in a business coaching/community earlier on in my entrepreneurial journey. I made a lot of silly mistakes in my first year – including overspending and focusing on the wrong audience – and was really frustrated. It wasn’t until I started working closely with Tara Gentile and her awesome community that I was able to see things more clearly. After implementing several pieces of advice, I’m now booking clients rapidly, hiring help to sustain the growth and most importantly, moving into the role of CEO vs. tired freelancer trading time for money.

Justine Grey of

17. Make industry friends – through masterminds or in person events! I spent my first couple years in business sitting on the sidelines, watching everyone else making friends but being too nervous to join in. Don’t be afraid to be awkward – just go for it! Having supportive relationships is a game changer!

Irene Hardy of Magnoliahouse Creative

18. I absolutely wish I had invested in more one-on-one education/mentoring instead of attending group conference after conference. The benefit of tailored, customized attention to your business cannot be underestimated!

Lindsey LaRue of Lindsey LaRue Photography
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19. I wish I would’ve invested in courses sooner. Yes, courses are an expense, but I’ve taken several fabulous ones that really saved me a ton of time and helped me to learn the important stuff in an organized and streamlined way. Being able to get educated directly from the experts, instead of wasting time doing my own research was a huge help to my business.

Jackie of Jade and Oak
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20. I wish I had made connections sooner. The first years of running my business were spent going in circles because I had no clue what to do! After joining some Facebook groups and getting an accountability partner things completely changed for my business. Don’t be afraid to step out of your bubble and make friends with other business owners.

Shaylee Smith of

21. I wish I would have started a mastermind group sooner! For anyone who doesn’t know what a mastermind is, I define it as a group of people who get together to offer support, feedback, and new ideas, that will help you progress from where you currently are. As soon as I started a mastermind and surrounded myself with other smart boss ladies everything in my business started to change. I had more clarity, got great feedback and was able to make decisions more quickly. I was also constantly inspired to do better because of what the ladies around me were creating. So as soon as you start your business I recommend starting a mastermind group!

Nevica Vazquez of
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22. I might have considered hiring a coach who was really aligned to my type of business and values! But I think above that I wish that I had invested in my email list/community sooner.

Danielle Joseph of Hello Function

23. The one thing I wish I had done sooner in my business? I wish I had invested in my skills and growth much earlier. I used to be very resistant to the idea of taking online courses, working with coaches, etc. When you’re stubborn and want to learn everything on your own, that can happen! Plus, it’s not always an easy decision to make an expensive investment in something like a high-priced course. However, I realized that sometimes you just need to learn from someone else who knows best. You have to be willing to trust in their expertise and you have to want to see results before you can feel comfortable with investing in your business. Once you take that leap and you begin to give back to your business and your own skillset, you’ll see results and it will all be worthwhile. So, don’t be afraid to shell out some cash on a course, coach, or another resource that will help you become a better business owner.

Rachel Moffett of Define your Hustle

Don't Work Alone, Find your Tribe

You're new to the freelancing game and struggling with working alone in a bubble. But you don't have to, you just have to know where to look for others like you.

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…started building their email lists earlier.

24. I wish I had focused more on a targeted email list in the beginning, and been more intentional with growing that list early on. Your email list is the life-blood of your business, without an audience (even a tiny one, like everyone has in the beginning), you’ll be trying to sell your products or services to crickets.

Kelsey Baldwin of Paper and Oats

25. The number one thing I wish I would have done years ago in my business? Grow an email list. I remember being so proud of my social media following, until my business coach asked me what I would do if it disappeared tomorrow. How would I get in touch with all of my followers? Silence. He was right. I had hustled so hard to create this following, but in reality, I was leaving the fate of my business in the platforms I was using. These days I care more about an active email list than Instagram followers because I know that my email list directly drives profits and relationships in my business.”

Jenna Kutcher of
Jenna has a more elaborate answer to this question, check it out

26. Start an email list. I was running a freelance web design business, building my blog audience, and launching ebooks and e-courses for TWO YEARS before I started my list. I had heard I needed a list over and over and over and for some reason didn’t think it would help. What I didn’t realize was that blogging + social media are for growing and getting to know your audience and email is for making the sale. Probably not surprising that my business got a lot bigger once I got my list going!

Sarah Morgan of XO Sarah

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27. Started an email list.

Joyce Gutierrez of Write Pretty Things

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…niched down in their businesses sooner.

28. Specialize in something. I started out wanting to offer #allthethings, but over time I learned that specializing in one thing and putting my all into that one thing will help me bring in more dreamy clients, more money and will also keep my sanity in check!

Maria Carras of
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29. I wished I’d focused on ONE thing sooner. I found that by being the go-to girl for one specific service, my influence grew a lot faster than trying to offer #allthethings!

Ashlyn Carter of Ashlyn Writes

30. Getting more focused in my offerings!

Katie Williamsen of

31. The one thing I wish I’d done sooner is stop wasting time on superficial stuff and focused on launching a signature service for a niche market. That is honestly the best way to bring in revenue fast. Once you do that, you can start using that revenue to build a website, do more online marketing, etc. I have to be honest: I think way too many online entrepreneurs are going into debt buying programs and wasting too much time creating a website when that money and time should be spent creating a minimally viable service and getting some clients!

Courtney Johnston of The Rule Breakers Club

BONUS. I wish I would have gotten out of my bubble and focused on building my tribe. The business ladies I have around me are sooo important to my success. They make it easy for me to compete with myself instead of chasing after someone else’s version of perfect.

Aleia Walker of
Want to know how to find your tribe? Grab this resource guide.

Motivated to invest in something yet?

There’s probably something here that pushed you over the edge. Something you’ve been doing (or not doing) that doesn’t feel quite right and you just had 31 bosses set you straight. If you’ve been waiting to find a coach, hear what it did for that person you admire. Thinking about getting a professional looking visual brand – it’s not just designers and developers who think your brand is important. Still doing all the things? STOP. And take a look to see what any one of these bosses do and similarly niche the heck down.

Don't Work Alone, Find your Tribe


You're new to the freelancing game and struggling with working alone in a bubble. But you don't have to, you just have to know where to look for others like you.

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  1. Hi, Aleia!

    Thanks, for mentioning my piece of word. It’s so good to read about that one help all these super-talented boss ladies wished they had sooner. I also realize these things have made our minds crystal clear. Now, we can invest and take best decisions at the right time.

    A wonderful roundup!

    Arfa 🙂

  2. Such great tips from awesome boss ladies Aleia! I wish I would have researched about blogging when I started my blog – – 😂😂😂 I had noooo clue. If only I had searched for + taken a “blog course 101”!

  3. Looooove this post and found it so helpful! I agree with each suggestion but I have to side with Lindsey LaRue on stating that I wish I would’ve invested in personalized 1:1 coaching sooner. And you’re right – building an unconditional tribe that encourages you and holds you accountable is EVERYTHING! Such a great post!

  4. Thank you so much for sharing these tips. I am a new business owner and I am going through these self doubts of whether I am ready for it all. Reading this brings me comfort that others have gone through it too and are willing to share their mistakes.

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