24 Things I Learned During My First Two Years as an Entrepreneur

In the spirit of celebrating two years since I left my career in Student Affairs behind me I thought it would be fitting to share 24 things I’ve learned since day one on my own. One tip, piece of advice, or lesson learned for every month I have been on my own to launch my passion project The Niche Movement, build my personal brand and harness my digital storytelling skills to start FYN Creative.

Some of these will be straight forward while others I briefly elaborate on. Some of my favorite and must-read’s are #1, #2, #7, and #16.

As always, many of of these can relate to our everyday lives personally and professionally as well as those self-employed or working for a company.

  1. It’s all about people. As much as I try to “scale” and grow my audience base for my businesses, I’ve realized all it takes is one person or one yes. One conversation could lead to that “yes” and really open up doors to make things happen. This works both ways with your employees and with your (potential) clients or business associates.
  2. When it comes down to it pick up the phone or meet face to face. As much as I preach social media and online connections, get away from emails and your devices. When it matters (whatever your it is), meet face to face. Teach face to face. Speak face to face. And when you can’t do that, pick up the phone. It’s faster, provides more clarity, and you can say what you want to say, how you want to say it the first time around while seeing or hearing the person’s reaction in real-time. You’ll be surprised at the upside and results.
  3. Find one person who will always be there for you. For me, it’s my wife Courtney 🙏. Not only is she an incredible wife, but at many times she’s been my advisor, counselor, proofreader, accountant, production assistant, and the list goes on. If you are thinking of going out on your own, it’s going to get lonely. You’ll need someone in your corner who get’s it, respects and trusts what you are doing, and can pick you up when you get knocked down. Because guess what, you’re going to get knocked down quite a bit.
  4. Put things into perspective. When you get knocked down or things don’t go your way, it’s going to suck. I have 15+ post-it notes in my office I created 4 months ago of all the things I’m lucky to have in my life including family, friends, employees/volunteers, physical and intangible items, and accomplishments. Make a list, hang post-it notes, or fill a jar when things go right to go back to when you’re down. You’ll need to keep the big things that matter to you in perspective.
  5. Have a grandma friendly soundbite to explain what you do. This advice was given to me by Kali Hawlk who was featured in my book. You need to be able to explain what you do to a variety of people — have some grandma friendly phrases ready.
  6. Have patience. Building a business or starting something from scratch takes time. The way I see it, my business is just a toddler, I can't expect it to run or feed itself.
  7. Serendipity is real. Timing is everything. Here’s my heartfelt example why I believe this.
  8. Work in 90 day increments. I do this for three reasons: goal setting, finances/budgeting, and milestones. If you’re just starting out, things are going to change quite drastically so you have to be nimble and if you can work and count on a 90 cushion to take you to the next step, you’ll be fine.
  9. Trust the process. If you have a desirable skill set and talent matched with work ethic and a little bit of #8, everything will work out. Trust me. The bigger deals take the longest time. Some of my business's largest deals (scope of work, exposure, and financially) have taken months of nurturing, following up, pitches, and patience.
  10. Under promise and over deliver. Define what that means for you and if you can do it with your clients, employees, and people in your life, you’ll be golden.
  11. Surprise and delight. Same as #10. Oh yea, do this on social media too.
  12. Accounting. If you are working for yourself and you can afford it, get someone to organize and track your expenses even if it is part time or just when you need it. For the last 16 months I’ve been using Freshbooks (not a plug) and it’s great, but I still have to go back and sort some expenses that are missed. This can be a time suck when you’re trying to grow a business.
  13. Billing. Invoicing and collecting money is no fun. Especially when a client doesn’t pay net-30. If you are a solepreneur or starting out small, you have to take the personal context out of it. Hire someone to send your invoices and to collect money. And if you can’t do that, create an alias email/employee and send it on their behalf. Trust me, when things get hairy and you need to be stern, you don’t want the work you’ve completed or your reputation to be put aside. #TimeSuck
  14. Handshakes are great, but get it in writing. To this day, I iterate and adjust my contracts and proposals. Learn as much as you can and have someone you know review them (thanks John G. and Michael D.) and ask for feedback. Don’t be afraid to add late fees, cancellation charges, and include who’s responsible for what.
  15. Be flexible. Sometimes when you’re starting out or when you want to get your foot in the door with a client you need to be flexible. My example: I’ve had plenty of client projects that have a quick turnaround or tight timeline, and because I’ve done work with them before and know them, sometimes we’ll get started before the deposit or fee for signing the contract. If you do it the right way, they’ll appreciate your nimbleness in addition to the product or service you deliver for them.
  16. Take a break. I just took a 15 minute break before sitting down to right this. Short or long, when you feel like you're out of steam, call it quits. There is always tomorrow.
  17. Answer every message. Whether it is email, Facebook/text message, tweet, etc. acknowledge them and reply. Bonus points if you can do it within 48 hours.
  18. Take every opportunity to connect. Going along with #2 and #17, if someone wants to connect with you (phone, in-person meeting, Skype, etc.), find at least 15 minutes to do so. There may never be anything that comes of it, but karma is a real thing. You’ll be on the other side of the coin and want/need to connect with someone at some point in the near future.
  19. Get out of the gray area. I try to eliminate words like would's, should’s, and could’s as much as possible. You’re either going to do something or not. You’re going to have the people around you so make sure they are on the same page as you and that they can commit. This goes for your employees, clients, bosses, and personal relationships.
  20. Twitter search. It’s a blessing for biz dev, reverse engineering content creation, getting a pulse of your industry, and gives you the ability to engage one by one t0 build your social media following/business. Here’s a short video I made this winter. Oh yeah, and humanize every piece of communication from your business.
  21. No more gatekeepers. I’ve been talking about this for three years but from a business/outreach/growth standpoint the same applies. We live in a time of limitless connection. No business or professional that you want to work with is out of reach. You just need to get creative, standout, and be relentless. I review this guide from Foundr weekly when I’m reaching out to hard to reach people. Check it out.
  22. Don’t take no for answer. A no could be no response, so follow up because 9/10 if done the right way they’ll get back to you. It takes 3–7 follow ups to get a deal done. And a real no, sometimes it’s worth the audacity to go back and ask again or position your offerings in a way that they can’t say no. I’ve done this three times so far and two of them have turned into contracts.
  23. Don’t be afraid to say no and hold your ground. This has been one of the hardest things for me based on my inclusive and “need to please” personality. However, there are times you need to hold your ground and even say no. Or hold your ground for what your services and time is worth. It could be the direction your work is going.
  24. Be transparent. Sometimes this has been difficult for me but I can’t tell you how being more authentic and genuine you are with your personal and professional communities has benefited me. That’s why I’m writing this. It’s honest. It’s real. And it’s true. We live in a time where we like the behind the scenes, reality TV feel and we also expect the truth. Please try this.

Thank you for reading and for all of you out there that have gone on this journey with me. Here’s to my entrepreneurship journey turning 3 🍻🎉.