5 shocks I got when I became an entrepreneur.


I grew up with an entrepreneurial spirit but didn’t know what it meant to really be one until six months ago. No longer part of a team or company, I had to learn what it takes to be an entrepreneur.

In the last 6 months, there have been 5 things that shocked me.

1. Hustle has an 11.
I like to think that I spent the last 6 years hustling at a 10. I’ve worked hard, learned as much as I can about social media and hustled on the opportunities I got. Unfortunately, the entrepreneur dial goes to 11. Go out on your own, I promise you’ll instantly be caught off guard by how many awesome things awesome people you used to work with used to do for you. Guess who does them now? You. So if you think you hustled before, you ain’t seen nothing yet.

2. There is no automatic money.
For the majority of my 16 years in the workforce, I had automatic money. By automatic money I mean that regardless of how my week went, I got a check. If I had a bad week, I got a check. If I had a good week, I got a check. Sure, if I was horrible I would get fired, but for the most part my salary just showed up. Now though, guess what? There is no automatic money. Money shows up when I show up first. I know that probably sounds obvious but I promise you this has been a hard lesson for me to learn. I’ve never had to chase it this deliberately. That’s why I’ve started to endorse the companies I personally use. That’s why I started consulting. I’ve done that for years for close friends and brands, but this is the first time I’ve opened up to a wider audience. This is the first time I’ve said, “Hey, I hit the New York Times list. If you’ve got a book you need help marketing, let’s talk.” Or “Hey, clients currently fly me across the country to help them with speeches, want to give the best one of your life? Let’s talk.” That’s a huge shift for me. To quote Jay-Z, “I’m not a businessman, I’m a business, man.”

3. You can’t go it alone.
Somewhere along the way we decided that “entrepreneur” meant “you against the world.” That’s nonsense. I need help more than I’ve ever needed it before. That’s why I have a business manager. That’s why I have a team that built this site. That’s why I have a speaking agent. That’s why I partnered with Infusionsoft. They do online marketing for some of the best companies in the world. I had one, one hour training session yesterday and it already changed the way I am going to launch my next book. Doing something as simple as reaching out to a company like them is going to radically change a lot of what I do, from the emails I send out to the relationships I build. But before I could put this partnership together first I had to admit, I can’t go it alone.

4. You build relationships or have none.
In addition to business relationships, you have to be deliberate about friendships too. I really liked the people I used to work with and spending the day with them was fun. Now though, I can hole up in Starbucks for 8 hours and no one would notice. That might sound great for a few days but I promise, the sense of loneliness as an entrepreneur is dangerous. You have to be intentional about connecting with people and building relationships in a very real way.

5. There is no such thing as a normal day.
Every day is different for me. Not just a little, but wildly different. Tomorrow I’m talking with a production company about a TV program. Thursday I’m flying to LA to work with a client. Monday I’m speaking in Orlando. It’s next to impossible to nail down what an average day looks like for me and I love that. It’s a little terrifying at times but once you get your feet under you, you learn to enjoy the waves.

I love being an entrepreneur. I loved working at companies. I think both experiences can offer a lot of amazing things in our lives. If you choose to go your own way, get ready though. You’re in for a few shocks of your own.

What’s one thing you’ve learned about being an entrepreneur?

About Author

Jon Acuff
Jon Acuff


  1. So true Jon! #4 especially, I have owned my own company for ten years in June. If you are not proactive it is a very lonely road. To go along with this you need people around you to tell you when your idea sucks. I have had a lot of bad ideas that trusted friends have saved me from. Keep inspiring Jon!

    • Jon Acuff Jon Acuff

      Congrats on owning your own company for 10 years! What type of work do you do?

    • Matt

      #4 hit home the most with me, as well. There’s a certain panic I got when I first started my business that made me focus on doing as much work as possible to keep getting paid — but without that intentional balance of reaching out to friends, it became very lonely.

      We’re getting ready to celebrate our 3rd year in business, I can only imagine the road for you to make it ten! Congratulations on the milestone — I had a client tell me once to make sure you don’t pass up celebrating the “little” things — breaking $100k in business, hiring your first employee, taking your first vacation, hitting 10 years.

  2. Wish I could say, not there yet. Watching and taking notes! Thanks Jon.

  3. Besides the shock value of these 5 things, which I agree with 100%, I think the difficulty level of said things was shocking. Number 3 has been the hardest for us. When you know you need help but can’t afford to hire help, it can be discouraging. I’ve found we’ve had to get creative on that front.

    I would add Be Open to Learning. There are so many skill sets we have had to develop that we did not have, but instead of giving up we had to resign to learn the skills even if they aren’t interesting to us. You have to do what you have to do! Loved this post.

  4. joanne

    You can’t live on your past. Just because you have repeatedly done great things before, the world wants to know what are you doing for them today. You have to keep investing in the future. Sort of a spin from the no automatic money concept.

  5. Never, never, never be afraid to ask. You never know what a bold email or phone call might produce.

  6. All of the above and failure often leads to your next success. So don’t diss the failures, they are launching pads for success if you allow them to be.

  7. These are all great, and spot on, Jon. One I’d add: It can’t be about the money.

    In my past 10+ years as an entrepreneur, anytime I subconsciously made the work about “making money,” the wheels flew off the whole endeavor. For one thing, people can sense when money is your goal, and quite rightly want no part of it. But also, “making money” is about getting, not giving; it’s self-focused, not other-centered. And it’s usually driven by fear. All that makes for a very unattractive message to your audience. And it’s no fun!

    All that to say, I’ve learned the work has to be about bringing your full gift in service of the world. And trusting God for the rest.

  8. Definitely that you have to work for it. I’m a college student in addition to being an entrepreneur, so finding the time/making the time to do this is really challenging. You have so much more you have to do for yourself than you would have to do if you had a “real” job, and you don’t get paid unless you do. I think the one thing I would kind of add to what you said (although I suppose it would fall under the category of “hustle”) is that persistence is key. Even when the going gets tough– that’s when you have to be even more persistent and hard working. Great post, thanks for sharing, Jon.

  9. Hey Jon,
    I think number one works in reverse too. If you are an entrepreneur building a team, its hard to let go of some of those things that you used to have to hustle to 11 to do. Its a shock to your system to hand over control and let your team do them, so that you can back off and hustle to 10 and maybe…just maybe get to enjoy some of the fruits of your labor.

    Now that you have had this experience, is there anything different you would have included in the book Start or the pamphlet you did on Awesome Ideas?

  10. I learned that I am never “off” work. Even when I turn off the lights, go home, and shut off my phone ~ my brain is still thinking, “how can I make it even better?”

    • Rachel

      Exactly why I told my parents (all four of which are entrepreneurs, step parents) I don’t want my own business; It’s just never over and is all consuming. But they don’t understand. Also the whole thing about automatic money is so appealing! Hence I’ll take a regular job any day. But that’s for me. I’m still thankful for all those entrepreneurs out there.

  11. So great to see your success and hustle. The automatic money thing hits home for sure.

  12. Nick

    So far I’ve learned that raising seed money will be hard for me. my jobs are preparing me, though, and I’ve learned a few things about myself and the people around me.

    1. I’m WAY more resilient under pressure than I thought.

    2. While my family always told me I could be anything, they get a little scared when they see me actually doing it. When I’m totally bought in and hustling, I can be a bit scary.

    3. My wife is the most supportive person I ever could have hoped for. I knew this in graduate school, but this feels even more real somehow.

    4. In an industry where no one is trusted, you make yourself that uch more special if you develop a real connection with your customers.

    5. Leading people is hard, but necessary, especially as a business grows. I’m among the best at what I do, and letting other people do their thing is a huge challenge.

    6. when you feel like stopping, don’t. That one last call/visit can be the success that turns an unremarkable pile of non-starter prospects into a HUGE relationship that pays for years.

    Wow. That turned into quite the list.

  13. Wow! Last night I made the decision to go out on my own and then I see this article posted on Facebook. I am both scared and excited to start my new adventure. Thank you, Jon for the heads up. Half the battle in starting out is not knowing what to expect. This helps tremendously. Thank you, again.


  14. Rick

    Would love to know why Dave Ramsey won’t mention your name on the air? So strange… On air Dave seems to be going off the rails.

  15. Jon,
    Thanks so much for sharing your journey as it changes and turns. Being a few thousand steps behind you, I find it encouraging and helpful to learn from you.

  16. I’m so grateful my friend recommended getting in on the hustle! I’m 44 and have been self employed for 25 years! This is my silver anniversary year as a picture frame shop and gallery owner. There have been many days where I’ve daydreamed about just getting up, punching the clock, then going home and being done. As an entrepreneur, I have no off switch…and I wouldn’t have it any other way! Turn the dial to 11!

  17. Laura Harris

    I have always had an entrepreneurial streak within me, but have never started my own business. In February, I graduated from Ramsey Solutions’ Financial Coach Master Series and am preparing to launch myself into the market as a financial coach. It’s an extremely exciting and intimidating time since as you said, the money doesn’t just happen. Thanks for posting these 5 tips; keep ’em coming.

  18. Larry

    Been an entrepreneur for 26 years. Don’t make decisions based upon today’s circumstances. Stay with the plan. Things can change for the better or worse in a heartbeat. Don’t be surprised and don’t be dismayed regardless of what happens.

    • Thanks, Larry! Though I’ve been self-employed for a few years, we are just starting to launch my husband’s woodworking business. I need the encouragement to stay with the plan. Much appreciated.

  19. It must be interesting to come out of a steady job to be an entrepreneur and it is interesting hearing you talk about number 1 and 2. My parents are both entrepreneurs and I dropped out of university and started my own business. I’ve only ever known the hustle, and I come from the opposite camp when people tell me about how they get away with slacking at work, or doing less than they are capable of… I can’t relate, for me if I do that I don’t eat and it is shocking that that is how a lot of the workforce is.

  20. Dave

    I have noticed that everything takes twice as long as expected. I get an inquiry from a customer. I get excited about having a new client then I don’t hear from them for a few weeks or months. Just as I think they decided against me, they call.

  21. Dennis H

    I would say plan for the best, but prepare yourself financially for the worst. Even if your working in the same occupation as you did when you worked for a company, your first few weeks or even months might not go as smoothly as they did with your company. I learned a lot goes on behind the scenes that you don’t see when you’re an employee.

  22. One thing I have learned is that a great deal of time must be spent on marketing and it is continual process of refining again and again.

    But not marketing like catchy commercials during the super bowl, rather I have enjoyed learning more about marketing that gets a direct response from consumers and gets results that can be measured.

  23. Jenn

    I eon a private therapy practice. I work 40 hours to get paid for 20. I love it but I have to be intentional about down time and schedule time off.

  24. Love this list Jon, so true! It’s funny but I have so many friends who can’t relate to #2 or #5 because of their experience with a job and not building something. I love the adventure of the entrepreneur life, even if it feels like riding a rollercoaster with no seatbelt and hanging on for dear life sometimes.

    Keep up the great work Jon!

  25. #2 – No Automatic Money!

    I hadn’t missed a paycheck since I was 18, so this was big one for me! Even though I had a savings cushion, it was a real gut check to see less money coming in than going out, and never knowing how long the money would keep coming in. Definitely encouraged me to keep hustling.

    The other part for me, I’m sad to admit, was how quickly I wanted to go back out and find a job again, more for validation than even regular pay. I’m a confident, do-stuff kinda guy, so realizing how much importance I took from someone else giving me money and power was shocking.

    Thanks for sharing Jon!

  26. Mark Gregory

    I have found also that there is very little time spent in the Goldilocks zone, where the porridge is just right. There is usually too little or too much work at any given time. It averages out to be just about right, but the ups and downs can be quite disorienting at first.

  27. One of the hardest things for me was leaving the ‘security’ of my full-time job to work for myself full-time last June. Being brought up to go to college and get a good job was a tough routine to break out of mentally for me. For me it wasn’t as much of the automatic paycheck, it was the automatic deadlines. It took about a month to get used to the free-fall of making all of my own deadlines.
    9 months in, because of #5, #4 has been one of the most difficult. Not having a normal schedule can make it more difficult to connect with people who do. I get to pick up my kids each day from school, but many times we don’t have a ‘weekend’ to socialize.

  28. I’m about to find out. Last fall I felt a nudge to leave my job and venture out on my own as a filmmaker/podcaster/blogger. Today is my last official day where I’ve been the last few years. I’m much more excited then nervous. God is good.

  29. Sweatpants. I learned…sweatpants.

  30. It has taught me that you have to be accountable to yourself.(not easy) learn the skills and practice them. And above all if it terrifies you then you should be doing it not avoiding it! You don’t have to be perfect you just have to “do”.

  31. HGH

    And when you screw up, it’s sometimes hard to get back in the saddle, but you simply have to.

  32. Thanks so much for this Jon. I’ve owned a carpet cleaning company (yes, a female owned carpet company!!) for almost 4 years now. Hard work got me an 800% growth last year. I started in my dining room on a pressboard desk and moved in to a 6000 sq ft office building today! I’ve learned nothing is just given to you because you are you and darn it, people should like you, you have to work for it!

  33. Bryan Orr

    I got more than 5 shocks when I became an entrepreneur. They all occurred when working on A/C units after I forgot to turn off the breaker – Wakka Wakka Wakka

  34. Hustle to 11, indeed!!! Nothing trumps EntreHustle.
    EntreHustle > Van McCoyHustle
    EntreHustler > NewJackHustler

    17 years as an EntreHustler. All I’ve ever known!

  35. DebD

    Maybe it’s just me, but it’s kind of funny that I was going to pin this article to my “Freelance” board on Pinterest, but alas, there is no appropriate picture for Pinterest to capture. Funny because of how much you hustle to get your name/business out there, and knowing you understand the value and importance of social media so well. 🙂 But seriously, good post. Thanks for writing and sharing it.

  36. I would say a combination of #1 & #2: there is no finish line. One of the motivators of an entrepreneur is that they think they can build a better mousetrap. That and they eventually get bored. It never gets comfortable, but that’s what keeps us moving and hungry. There’s actually less ambiguity owning your business than working for someone.

  37. Yes! I’ve been a follower of yours for about 8 months.

    I’m 14 months in with my first business. For many months I didn’t know how I was going to make it. I was working 80+ hrs and nothing tangible to show for it, no automatic money. My dad kept saying, “When are you going to get a real job?”

    I stuck with it. Business and income are getting better by the day! Thanks for sharing!

  38. It’s only hit me very recently that being a full-time writer means I’m also an entrepreneur. Which is very funny, because I don’t want to be a businessman. I just want to write. Joke’s on me.

  39. Ted


    Amazing list – and so true. My father and grandfather both are entrepreneurs so when I set out on my own a year ago – I thought I had the genes and it would be natural. Little did I know how difficult it is – AND also how gratifying it is to know you make it happen each day. One day you want to quit, the next day you feel like you are king of the world. If you can stay consistent and really have poise (never to high, never too low) and continue to add value to your customers, you have a great chance of moving forward and succeeding. Saw a link here and this is the first I have seen your blog – love it already. Keep up the great work!


  40. Billy

    9 months into building my own financial practice. #1 and 2 are minute by minute realities for me. Thanks for this post and encouragement

  41. Nothing I disagree with on that list Jon. #1 and #2 have been particularly sobering for me. Profits have started to get consistent, but not where they need to be. Finding time and balance for marketing, sales and the work is a little fuzzy right now. Have any handy percentages of how much time per day or week to spend on the different parts of your business?

  42. Learning to say no has been hard for me. When you’re an entrepreneur, at least in my profession, it’s feast or famine. It’s hard to turn down a great paying gig, even if you’ve already made family plans, when an agent calls because you don’t know how long it will be before the next one. I’ve rescheduled vacations to fly from one show to the next on several occasions.
    Now, I’m trying to find balance and keep certain commitments while trusting God will make up any monetary loss. He’s always provided.

  43. Jon,

    The money point is ridiculously true, and I’ve found it’s inverse is also true. When I “truly” show up, money does too. I’ve had multiple instances where I’m busting my butt for days or weeks, and not making a lot of progress on whatever I’ve been focussing on. Out of the blue, I’ll trip over an opportunity, or a former client that I haven’t talked to in months or years reaches out to me.

    The other point I’ve noticed, as a business owner after hours doesn’t exist, and work life balance is a myth. I am my business, if I’m “off”, my business is closed.

  44. This list is spot on. I have students ask me all the time what it is like to be self-employed. I always tell them it is the most exciting, rewarding, hardest work you will ever do. I’m going to share this post with them.

  45. Such great advice! Excited for you and your new journey.

  46. I’ve learned that you find out who your real friends are. At first everyone is excited about your new venture, but also anticipating that you will fail. After a while most of them go away and it’s your real friends and customers who keep you in business.

  47. I am in my 6th year of being in business for myself full time. When I left my 22 year corporate career to start a guitar repair and lesson business, my biggest fear was that I would run out of work or students. That has never happened. Quite the opposite. My business grew from a home-based lesson and repair business to a full retail guitar store in a few short years. I employ 2 part time workers and currently have more repair work and more students than I’ve ever had. It takes a lot of my time, but it doesn’t feel like work because I go to the shop every day and do what I love. The key is to do something you’re passionate about, find a niche, have multiple revenue streams, and work hard at it. I’m also in the process of writing a book, so any advice you could give me on that would be appreciated.

  48. Janis

    Never quit learning. Never quit advancing your skills. That’s where I am. I got comfortable in my day job. The learning curve of new skills can be overwhelming. But, just the fact that you mentioned infusionsoft and book launches tells me this hard work will pay off.

  49. I’ve learned that you have to figure out what works best for you. You can’t copy someone successful and expect to get the same results, we don’t see the behind the scenes stuff of what they did. We can learn from their example but put our unique spin on it.

  50. Jon,
    Very timely blog post for me as I have one week left at my job. 9 weeks ago I gave my 10 week notice that I would be leaving my job of the past 10 years with a large Christian outreach Ministry to join my husband in our family businesses. While there are still scary moments of leaving behind a job I enjoy and people I have come to know as family, I believe I’m making the right decision. I look forward to all that being an entrepreneur has for me. Thanks for your post!

  51. What I have learned? I can be an entrepreneur and it doesn’t have to be an all-or-nothing proposition. I am taking gradual steps, asking for help, surrounding myself with other entrepreneurs who are awesome . Two years ago, I would have NEVER imagined I would even entertain the idea. After learning from Dave Ramsey and then his team (Chris LoCurto, Jon Acuff, Chris Hogan ) and a host of experts I have had access to through that experience, I have completely shifted my mindset. I had attempted owning a business before and miserably failed. I put a lid on that idea for 20 years, thinking that being employed was the only career choice for me. As of March 24, I am a business owner!

  52. Indeed it is a wild ride! I could tell this was sort of going to be your destiny since I started following SCL several years ago. It can be scary at times but the good Lord will lead you through. Be Great Jon!!

  53. I think everyone can learn something from #4 in particular. Friendships are always hard work.

  54. The myth that I would like to bust is being a solo-preneur is simply non-existent. I encounter “solo-preneurs” frequently that indicate they don’t have employees…just “team members”…therefore they are “solo”….malarky! You cannot build a business, or if multi-passionate like my wife and I, several businesses by yourself! Whether your “team members” are “employees”, “IDCs”, virtual, local, or imaginary…you will learn extremely quickly that we were not designed to live, or work, alone.

    Jason Ansley
    Full Service Business Development Firm

  55. I definitely agree with this list–especially the relationships part! I’ve owned my own business for the past 6.5 years, and I’ve felt very alone (even though I have an awesome staff now and an awesome support group) for most of it until I started to get intentional about building new and exciting relationships (and maintaining the ones I already have). 🙂

  56. re·sil·ience [ri-zil-yuhns, -zil-ee-uhns]
    the power or ability to return to the original form, position, etc., after being bent, compressed, or stretched; elasticity.
    ability to recover readily from illness, depression, adversity, or the like; buoyancy.

  57. Bekah

    These are all very true!!! Anyone who is working on becoming an entrepreneur should read this! This June will mark my first year as one. I have had to learn almost all of these the hard way. I love to live by a strict schedule. I have learned as an entrepreneur it is impossible. I love it now because I ask the Lord daily to lead me to where I should be that day. I have had so many great encounters that would’ve never happened if I had tried to enfource a schedule.

    I have also learned that those who are your first customers are very important to the success of your business. If you develop great relations with them, they will do what they can to help you succeed! 🙂

  58. If there is an opportunity in the market seizing it can make you a lot of money! But it might disappear as quickly as it came. You can’t depend on a single thing to fund your business… I earned a great amount of my money towards college by doing government grant programs teaching parents how to love and nurture their kids plus give them a love of reading… but when that program goes away so does your work 🙂

    (Ironically, I was a single 18 year old at the time teaching parents how to be better)

  59. 1 – Your attitudes about money changes because if you’re successful, everything shifts by at least one zero. Income, bills, taxes, …. everything. And that’s terrifying at first.

    2 – Putting together the right technology and services infrastructure to support what you do gets harder as you get more successful.

    3 – The high you get from attention and positive feedback from strangers is not meant to sustain you.

    4 – Don’t confuse people’s interest in what you do for them with interest in you.

    5 – Don’t confuse what makes a fun pastime for a genuine passion. Anything business that actually works will require a period of intense focus and so much work that if you don’t have a deep genuine passion for it, you’ll burn out.

    6 – Choosing work over people doesn’t improve your enjoyment of people, but choosing people over work can change your enjoyment of work.

    7 – You don’t have to explain or rationalize success to anyone, just be a good steward of it.

    8 – Some customers can’t be fired fast enough, but if you turn the right one around they’ll be your best supporters. It’s your job to tell the difference.

    9 – Keep a daily work log of what you worked on. Use it to confront the fear that you haven’t gotten any work done this week.

    10 – People can’t buy what you don’t have to sell, or what you didn’t finish, and they can only pay as much as you ask.

  60. I so badly want to work only for myself but know the security that comes with a steady paycheck outweighs my desire to take that flying leap at this point. I think the biggest thing I’ve learned in the 6 months since starting a business is that it’s incredibly overwhelming and a lot of people much farther ahead of me try to tell me all that I need to do which overwhelms me even more. I think the hardest thing is to eat the elephant one bite at a time instead of getting down on myself for all the things I haven’t gotten to yet.

  61. Ketra

    I appreciate this post so much and agree with all of it. When people do start makimg money I would caution them to be careful to set aside money for taxes! They are no longer being taken out of your “pay check”. You will have to be dilegent to stay ahead of the game.

  62. Everything about this is so true. I left a stable, “normal” job a year ago to start my own graphic design business, and man, this has been hard, but so good. I keep telling my husband “people don’t understand how easy they have it when they know they have paychecks coming”. I love what I do now, but I get way more excited about every payment I get because I know that I seriously earned that money. And then I pay my taxes… ow.

    I’ve also noticed the loneliness thing – I’m sure my husband doesn’t mind me working from home since now I cook and clean on my lunch breaks, but I’ve started scheduling an intentional weekly “social interaction” so I don’t go crazy. We need that interaction, even if it’s just one cup of coffee per week to remind us that our business isn’t our life.

  63. Great list on things to keep in mind before taking that step for us that hasn’t yet. You’ll do great consulting and can’t wait to see what kind of cool things I can buy from your store too.

  64. I’ve just taken a leap of faith as an entrepreneur and launched my own website this month for my Life Coaching/Speaking/Writing business. This post is very timely. Thanks!

  65. I love this! I never thought I wanted to be an entrepreneur, but I’ve been a freelance graphic designer for more than 5 years now and there’s no turning back! I’m thrilled that I’ll be launching a second business soon.

    The “no automatic paychecks” part was one of the hardest things for me at first. But there are ways to generate regular income in almost any field; it just takes a lot of hustle to get things rolling.

  66. Hello John … Hope you and Jenny are doing well!

    1. As a journalist, my day is structured only to the extent that I have to get “product” out. That could be an interview, news release, Facebook posts, feature, review, or some days, all the above. The catch? I never know which way it will go, or when. So, I have to be flexible, alert, polite, friendly, helpful, and upbeat as much as possible.

    2. I interview famous artists, and music industry people regularly; sometimes I’m sitting across from one of my idols! I try my best to treat them like regular people, I show them respect for their standing, and I am interested in what THEY have to say. I have to listen. I have learned so much that way. Also … I am always prepared for these interviews because to me, if I am not, I am not showing that person respect for their time. Not cool.

    3. When you treat others well, for the most part, they will do the same. They will remember you in a good light. I can not tell you how many friends I have made that way.

    4. ALWAYS do your best work. Word gets around, and your work will speak for itself.