150+ Years of Entrepreneurial Experience: What I Wish I Knew When I Started

Have you ever wondered what experienced entrepreneurs would go back and tell their younger selves in business? We did and decided to find out! We asked creatives in the UPWRD Accelerator by HoneyBook, including photographers, designers, brand strategists and copywriters two critical questions: What is your best business tip for other entrepreneurs and what is one thing you wish you knew when you started your business? Here’s what they have learned in their over 150 combined years of entrepreneurial experience.

Top Tips for Small Business Owners

Allison Sugahara

If you’re ready to level up your business, first assess where you’re spending your time where you really shouldn’t be (or consider the things you hate to do the most). After all, you started this business because you were passionate about your craft! In order to “duplicate” yourself, you’ll need to create + document a process for tasks to be delegated. Don’t forget to factor your overhead costs into your rates!

Allison Sugahara
Founder of Polygon Market
Website + Instagram

Andy Lydick

Believe in yourself. You are your brand and your biggest asset. Don’t be afraid to put yourself out there because people are booking you for you. Make sure to be clear about your mission statement and why you do what you do. Potential customers will connect with businesses who have their story out there, give them a chance to relate to you!

Andy Lydick
Photographer
Website + Instagram

Josefina H. Sanders

One thing I wish I knew when I started my business was that there are resources, therefore use them. A lot of the questions we have when it pertains starting our own business journey can be found. (ie: Rising Tide Society helped me a ton.) And if not, don’t be afraid to ask for help.


Josefina H. Sanders
Author and Creative Freelancer
Website + Instagram

Brina Braun

Find a community! TuesdaysTogether by the Rising Tide Society was my first creative group I ever joined and it was amazing. Attend workshops or retreats and you get the same community of people to lean on and learn from!

Brina Braun
Photographer
Website + Instagram

Marirosa Anderson

Regardless of how long you’ve been in business you have to continue to educate yourself and know we are always learning. One thing that really helped me was surrounding myself with a village of not only supporters but those that I could trust to be honest, good or bad – that allows me to bring in different views as I continue to grow my businesses.


Marirosa Anderson
Founder of Amor Latino Unveiled and Photographer
Website + Instagram

Bree Pair

I joined a mastermind group one year ago, and we just had our second retreat. This was the best investment I’ve ever made in my business. These women push me every single month to be better, check me in places I need to fix or slow down on and have been incredible in helping me with the growth of my company. We check in with each other weekly via chat, monthly via zoom calls, and yearly with a retreat. Without them, I wouldn’t be as far along as I am. Find your people. Find a mastermind, start a mastermind, find others that are committed and that care about your success. Our group is truly one of the community over competition.

Bree Pair
Founder of Thrive Together Conference + Blog
Website + Instagram

Marvin Flavien

First: I hired a mentor and business coach who taught me how to sell my services and understand how I am changing the world. It took me from a struggling freelancer to a business owner.

Second: I learned how to sell my services at higher rates and make a true living. Could I have figured this out on my own? Yeah, eventually… but being able to have someone guide me and give me all the tools I needed to succeed was everything for me!


Marvin Flavien
Creative, Speaker, and Videographer
Website + Instagram

Chelsey Morphy

I had a problem pricing my services. My goal was to slowly increase my services per project, but years went by and I was no further ahead. I finally had a sub-contractor tell me my prices should be increased 3x. That increased evaluation coming from a 3rd party in my field gave me the encouragement to raise my prices 2x without blinking and I am currently working towards that 3x goal. If you’re hesitant to increase your prices, get someone else to do it. Sometimes it’s hard to recognize your own worth.

And read ‘Breaking the Time Barrier’ by Mike McDerment for those stuck on hourly rates.

Chelsey Morphy
Building Designer
Website + Instagram

Bailey Aro Hutchence

Be bold, be vulnerable, and share your journey. You’ll not only inspire others to move forward through the rocky patches, but you’ll build brand loyalty in a way you simply couldn’t if you only shared the shiny, happy highlight reel. People connect with honest storytelling – don’t be afraid to tell yours!

Bailey Aro Hutchence
Photographer + Educator
Website + Instagram

Karina Ramos

My best business tip for other entrepreneurs is to invest in support early on. You can not build your empire alone. The most successful people have mentors and teams in place to help them achieve success while they stay in their zone of genius. Don’t wait until your business has exploded to then organize your support team. Start now!

Karina Ramos
Business Coach and Podcaster
Website + Instagram

Brooke Michelle Jackson

Honestly, I think my best business tip for entrepreneurs is take quarterly reality checks. It’s so easy to get caught up in what everyone else is doing with their business, and while it’s great to attain inspiration, it’s just as great to show the world your truth. There were so many times early in my business where I found myself starting a project or swayed towards some other brand because I felt “that’s what made them successful.” It was draining.

Not only is success not a one size fits all type of thing, but it’s so hard to pretend to be something you’re not or fuel a project that your heart isn’t 100% passionate about. Take a step back and ask why you do what you do and then run with that. Because there will always be someone out there looking for exactly what you offer to the world.

Brooke Michelle Jackson
Yoga Instructor and Photographer
Website + Instagram

Cassidy Mister

Investing in a client management system to get you organized and streamline your business. As soon as I began using HoneyBook, I began booking clients faster. Clients trusted my platform and my professionalism by simplifying all stages of their process.

Cassidy Mister
Photographer
Website + Instagram

Praise Santos

Rest & play are essential tools in the entrepreneur toolkit. We often set out to work for ourselves for a better quality of life but can get so caught up in the do and hustle that we burnout or get pulled away from enjoying it. Whereas the habits of cycling work and rest is how we can really thrive.


Praise Santos
Founder Ethical Weddings and Photographer
Website + Instagram

Amber Lanphier

Know thy self! You are 50% of every relationship you ever have, business or personal. Taking an active role in self-awareness and personal development is hands down my most crucial tip for growth. You are in control of so much more than you realize. The mental wherewithal to problem-solve comes from personal development and overcoming challenges. Look inside and challenge your weaknesses with tasks that grow those parts of you. Celebrate and embrace who you are called to be. It is my dream that more people come alive with what they are passionate about and walk it out with purpose. Stay curious and keep digging!

Amber Lanphier
Photographer
Website + Instagram

Holly Gray

The best business tip is to lean into what makes you different. Too often we try to be the vendor for everyone but it’s smart to focus on your specific ideal client.

Holly Gray
Founder of Anything But Gray Events
Website + Instagram

Amanda Freeman

Don’t stay in the shadows. Meeting other like-minded (and sometimes not so like-minded) business owner friends has helped me grow my business by leaps and bounds. Diving in and going to networking events, reaching out to that girl that is BUSINESS GOALS to see if she wants to grab coffee, opening up and talking shop in a Zoom call. All of those things can be quite intimidating and being seen is sometimes the scariest part of all of this, but taking the chance and really getting to know people who get it is why I am who I am now. The people I have met are my community. The good, the bad, the straight up nonsense. They get it. And because they also took the chance and opened up about failure and success, the chaos, the wins and losses, I know I am not alone.

That has made all of the difference.

Amanda Freeman
Branding + Web Design
Website + Instagram

Madison Short

Have people that you look up to, but don’t try to be like them. You won’t attract your ideal client if you are trying to be like someone else, and there is a whole bunch of people who are waiting to hire someone like YOU.

Madison Short
Photographer
Website + Instagram

Breanna Kuhlmann

My best business tip is to take time to invest and learn how SEO works. Take the time to learn the best practices to get your website noticed on the internet! My number one SEO tip is to create your own landing page for your Instagram bio! It’s a simple step to drive traffic to your own website. All the clicks will get your website noticed on Google.

Breanna Kuhlmann
Photographer
Website + Instagram

Caitlin Strempel

Don’t be shy about what you do…on AND offline. In today’s digital age people forget to promote themselves offline too! I find so many clients by just talking passionately about what I do with people I meet and hang out with. I even found my very first client at the gym… again, by just talking about what I do.

Caitlin Strempel
SEO Expert and Marketing Strategist
Website + Instagram

Wade Foley

Don’t be afraid to fail. Take risks, bring on new team members, surround yourself with the right people, let the wrong people go. The best way to grow is to dive in, fail, learn, do the work, and repeat.

Wade Foley
Social Media Manager
Website + Instagram

Justina Michaels

Do your research and continue to find new ways to pivot and innovate your processes. I thought that concentrating on my current clients was the most important part of running my business but taking the time to rethink and refine every moving part has gotten me my IDEAL clients. I’m learning to carve out more time to evaluate what’s working and learn new apps and programs that can help streamline my workflows even more, allowing me to spend more time with people which is really where I can shine!


Justina Michaels
Founder of Fitting Fêtes
Website + Instagram

Gillian Paterson

Create a passive income source for your business!! It doesn’t have to be big, something small will do! I created my first tiny passive income source a year and a half ago. It was a small one page branding board that took me maybe 15 minutes to draw up. Since then I have sold it for $2 a piece, used it as a lead magnet, and also given it away as a “freebie” on Creative Market. This tiny $2 branding board has taken in over $4k of revenue and has taken up a total of about 30 minutes of my life, graphics and all. Even something small can have a big impact over time.

Gillian Paterson
Branding and Web Designer
Website + Instagram

Haylee Gaffin

Focus on something you’re passionate about, then find the problem that needs to be solved in that area to create a brand that people didn’t realize they needed.

Haylee Gaffin
Digital Marketer, Podcast Producer, + Photographer
Website + Instagram

Maggie Hargrave

Having other smart entrepreneurs in my life to hold me accountable was huge for me. I don’t know where I’d be without friends who I can count on and talk to. Another example of when the needle moved for me in terms of business and personal life balance was when I started outsourcing more: CPA, blogging, office admin tasks, editing, etc.

I felt more balanced in general, which was huge for me.


Maggie Hargrave
Photographer
Website + Instagram

Lisa Robbin Young

Trust yourself and keep your eyes on your own paper. It’s so easy to get distracted by what everyone else in your market is doing, start trying to do ALL THE THINGS, and forget what you’re on this planet for. Stay focused on yourself, your business, and YOUR Great Work. Let other people be a benchmark, but only compare yourself to who you were last year. If you’re better, rock on. If you’re not, well, you can’t unsee that, so what are you going to do differently?


Lisa Robbin Young
Author and Speaker
Website + Instagram

Michele Perry

Because I still deal with TBI-related memory issues, I started creating templates and workflows for everything. Best tip: If I touch it twice it gets a template and/or a workflow written out so I don’t waste time “remembering” how I did that.

I started this to keep myself organized. But the tools I’m developing to keep myself sane are growing into a product shop serving the needs of creatives and entrepreneurs. I always ask myself when I develop a new tool for my own use, if it could benefit others as well. That way it pulls double duty and creates a passive income stream as well. Win, win, and… win.


Michele Perry
Creative and Strategist
Website + Instagram

Emilie Steinmann

Don’t be afraid to run your business at your own pace. We are all uniquely equipped for this journey and all have the ability to reach our own definition of success. Stay on your own path and stay true to the pace that works best for you.

Emilie Steinmann
Marketing Strategist
Website + Instagram

Michelle Simmons

HELP, don’t sell. When you can tell/show your target audience how you’re actually solving the problems they have, you (1) form a personal connection, (2) build trust, and (3) show off your expertise… all without coming off as a desperate salesperson. And then they’re a LOT more likely to remember you and BUY from you.

For example, I like to use the 80/20 rule in my messaging + even on my website… 80% of the time, I’m posting something to connect, inspire, and educate. Then the other 20% of the time, I’ll mention my services + current promotions.

BONUS: All the inspiration and education you provide becomes part of your PERSONAL BRAND, which helps sets you apart from your competition!


Michelle Simmons
Brand Photographer
Website + Instagram

Jaime Wright

I wish I knew how lonely the creative entrepreneurial journey can be. Building a creative business and working from home was relatively new when I started doing it, and I couldn’t relate to many other people I met in local networking groups. If I could go back and change something when I began my business, I would start earlier in building a community of people who could relate to my journey. It means so much to be able to have people now who understand what it’s like to be a solopreneur and build a business online!

Jaime Wright
Marketing Strategist
Website + Instagram

Jasmine Norris-Dixson

Time how long it takes you to do the different activities of your job. This will not only help you price your services for profit but will also help you plan your schedule so you can consistently meet your deadlines and lessen stress.


Jasmine Norris-Dixson
Photographer and Educator
Website + Instagram

Jessica Freeman

Niching down is when everything opens up! You might think you’re closing off potential clients, but guess what? You can niche down your marketing to a specific group, and still work with people outside of that niche if you want. When you let people know you specialize in working with a specific industry, you quickly become the go-to expert.


Jessica Freeman
Designer for Wellness Coaches
Website + Instagram

Jennifer Mejia

Invest in your business. If you’re serious about growing—INVEST IN YOURSELF. Some things I’ve seen a return on: a mastermind or coaching program, joining publications (the right ones!) with ads, branding, a gorgeous website, HoneyBook!

Figure out what you need the most and make a list for your future.


Jennifer Mejia
Photographer
Website + Instagram

Shaunae Teske

My best piece of advice for business owners is to define what success looks like to YOU and go after it like crazy. Instead of chasing what you think you should be doing, it’s important to look at the life you want to cultivate for yourself. It will help you when comparison creeps in, you won’t have to give it any power.

Because you know what your success is. Always work on improving and growing to become the best YOU that you can be. Don’t worry about what anyone else is doing. You have everything you need to succeed.


Shaunae Teske
Photographer and Educator
Website + Instagram

Michelle Caldwell

Don’t underestimate the power of your mindset! I’m talking about the things you say to yourself, that little voice in your head. Success is merely a mindset!

Running a business can incredibly overwhelming and feel like a wild rollercoaster at times but if you can take a deep breath and have faith in yourself that you CAN do this, you will succeed! Plus, almost every problem you might have is pretty much google-able.

Oh, and having a badass business software like HoneyBook will help too!


Michelle Caldwell
Photographer
Website + Instagram

Loren Jackson

Blogging is NOT dead. It’s still extremely valuable. If just starting out, blog 2-3x a week. If you already have a decent amount of evergreen content on your blog, you can get away with blogging once a week and spending 3-4 days marketing that content EFFECTIVELY.

Keeping a running list of blogging topics in a note on my laptop has been a great place to brain-dump when ideas come to me. Then spending 2-3 days a month writing all my posts at once keeps the blogging calendar full and flowing.


Loren Jackson
Photographer
Website + Instagram

Kristin Reuter

Outsource, outsource, outsource! Everyone was saying it, every business owner I asked recommended it, but I just didn’t want to pull the trigger. I loved that I took care of every aspect of my business for my clients, but I was drowning in work. I just could not keep up. I also did not think I could afford it. I finally started outsourcing and I cannot tell you how it not only took a lot of the workload off my shoulders, but it is the sole reason I am able to grow my business beyond just myself. I am able to actually help more clients because I am able to focus my time on helping and creating for them while my editor and assistant take care of the other things behind the scenes. Which means because I started outsourcing I am actually increasing my revenue!

It’s a total win-win. I wish I would have started outsourcing sooner. Start small with one thing, and move from there. You don’t have to outsource everything all at once.


Kristin Reuter
Photographer
Website + Instagram

Noelle Abarelli

You are the average of the five people you spend the most time with. Find a community that challenges you to be your best and supports you on your journey to get there!


Noelle Abarelli
Marketing Strategist and Copywriter
Website + Instagram

150+ Years of Entrepreneurial Experience: What I Wish I Knew When I Started from HoneyBook

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