Get Your Head in the Game: Entrepreneur Edition

Last year my sister, who historically knows very little about sports, joined a Fantasy Football team with her friends. She (along with the rest of our family) expected her team to do mediocre to absolutely awful since she didn’t know anything about her players aside from their stats on the app. And then in the first week, to all of our shock, she won in a landslide. This motivated her to actually learn about the NFL players on her team and start seriously managing them, including picking up and dropping several players throughout the season to make sure she had the best odds to win. Between trying to win her league and Travis Kelce dating Taylor Swift, she became a casual fan of pro football (which made our dad ecstatic).

Sometimes small business owners get lucky the way my sister did with her fantasy football league: they start a business without knowing much about how to run a business and reach an initial high level of success, and then they find they need to learn more of the technical info to help maintain and manage that success. Unfortunately, these “quick to success” business cases are the vast minority. Most entrepreneurs need to know and understand a little beyond the basic principles of running a business and have an understanding of marketing, cash flow management, and team management before they really make a name for their business.
For the majority of small business owners, studying entrepreneurship was not part of their schooling, meaning that most small business owners probably lack important knowledge in the range of skills it takes to run a business. However, just because you’ve decided to run a business doesn’t mean you should have to go back to school (and potentially go into student debt) or pay an exorbitant amount for multiple online courses that are only semi-useful to feel confident as a small business owner.
So, since it’s the fourth quarter of the year and our team needs some creative new plays, here’s “Get Your Head in the Game: Entrepreneur Edition”, a collection of free and paid (but affordable) practical resources Upwell offers that can help you get your head in the game by learning more about how to effectively run a business! With a side of football puns, of course (sorry, not sorry).
*To be clear, I’m not claiming these resources will equate to a college degree in business, but they are affordable ways to learn more and feel more confident.
First Play: Blog & Run
Okay, team, for this play we start by looking for an opening to find useful information and then we run with it. Upwell has a pretty vast collection of practical business blogs (like this one) for entrepreneurs to reference. Here are my top 5 recs for small business owners to learn more about growing your business – for free:
- Your Guide to Understanding and Setting Business Goals
- How to Navigate Planning for that Next Investment or Team Hire
- Building a Marketing Funnel for Your Business
- Creating A Results-Driven Marketing Strategy
- Demystifying Process Automation: A Comprehensive Guide
Read these blogs to get a better understanding of some useful business skills and then personalize the advice for what your business needs.
Second Play: Watch, Rinse, Repeat
Our next play begins by studying what worked for other teams, adjusting it to your team’s strengths, and repeating the refined process yourself. Aka, watch our YouTube channel. Upwell has a (relatively new as of summer 2024) YouTube channel, and our bank of practical video tutorials will only get bigger. Subscribing is an easy way to find and continue finding some easy-to-understand, free information on everything from profitability analyses to custom services pricing. Especially if you learn better through watching than you do through reading. Follow this link to find our YouTube channel.
Third Play: The Vault
Here we start by guiding our quarterback through the defensive line so he (or she) can push into the endzone. Upwell’s digital shop, the Visionary Vault, offers a variety of trainings and templates (for less than $80) that are incredibly useful for entrepreneurs. Our top two educational resources are the Team Capacity Planner & Masterclass and the Strategic Offer Planning Guide & Masterclass. Check them out in the Visionary Vault to see if they’d be a good fit for your business needs!
Overtime: The Hail Mary
Finally, a real play name that makes a good pun! For anyone who’s not that into football, a “hail mary” is a risky play taken as a last resort. Luckily for you, though, Upwell designed our services with the intent of never asking you to take a big risk. Instead, we go through an affordable Systems Audit first so you can have clarity on the best course of action for your business growth and can make an informed decision to work with us on more extensive operations projects.
If none of the above resources do the trick, and you’re looking for help creating your operations strategy, automated systems, efficient processes, and more, the Systems Audit & Strategy may be just what you need. It’ll tell you exactly what your business needs and recommend how to get there, with the option of us helping you further if you’d like.
Game Review
I hope this was a helpful list of resources so you can finish the year strong and start 2025 confident in your capabilities. Or that you at least enjoyed the football jokes. Now, get out there, play hard, and go all the way to the championship!

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Get Your Head in the Game: Entrepreneur Edition
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