8 Entrepreneurial Insights I Wish I’d Known Before Leaving My Day Job

Jan 10, 2024

After spending 20+ years in corporate America, I took the leap and went out on my own as an entrepreneur. It has been “har-some” (hard + awesome). I have learned A LOT!  I get a lot of friends and former colleagues calling me and asking me “what’s it like,” to be out on my own. So, I created this blog post to capture my learnings in the first couple years of being my own business owner.  I hope these eight lessons refine your own thinking around the choice to stay in a role or go out on your own.  

1) What the heck is my identity?

I greatly underestimated how I define myself as a corporate executive. “Hi, I’m Reagan. I am an executive at Amazon.” Clean. Easy. Now I am a speaker. I am coach. I “unblock leaders so they can scale their leadership and careers.” HUH? People don’t understand what all that means. They ask me, “Are you like a motivational speaker?” YIKES. That conjures up visions of people in the 80’s selling cassette tape sets to visualize your future success.  

Tip: Be prepared to re-identify yourself. It might take a few tries. You might need to practice calling yourself an entrepreneur. You are a small business owner. You are now identified by the service you deliver and the problem you solve, not the company you work for.  

2) Oh paychecks…how I miss you.

You don’t realize how much security you have in that weekly or monthly pay. All of a sudden, you don’t eat, if you don’t hunt for business. The lack of stability can be jarring. Even if you save, you have to dip into savings. You know mentally you are supposed to do that, and it is why it is there, but it is still hard. 

Tip: My life got easier when I became an S Corp and was required pay myself regularly a “fair salary.” Set up a way to pay yourself in increments. Re-create the habit of being paid regularly vs. hoarding or just moving over a little at time.  

3) Experimental mindset.

Best advice I got from my friend Tonia Degner, “Reagan what you think will work, won’t. What you don’t think will work, will. So, have an experimental mindset” This mindset led me to say “yes” to a lot of things last year that maybe in the future I won’t say yes to. Or things I didn’t have on my radar that I LOVE. I have nine business founders on my coaching load which I did not expect. I do a hybrid of coaching and consulting with them…and I love it. They love it. I never had that even on my radar but I said “YES” to an offsite for one of my coaching clients and it led to several founders referring me to each other. This kind of experimentation is not always praised in corporate life where every project every is “green” no matter what (even if that means you have to move the date out).  

Tip: Make plans. Hold them loosely. Pursue opportunities aggressively. Try them. Learn. Be ok with failing. Just gets you more focused on what you really want and is realistic.  

4) Ramp before you leave, then cut across traffic and turn left.

I wrote a book. Got my coaching certification with ICF. Saved money. Spoke every chance I got to hone my skills. But at the end of the day, you will just have to leave. It won’t be elegant or pretty. Almost everyone I know had preparation + life event that forced them out of corporate because the hurdle to leave is so huge.  

Tip: Prepare like crazy for your business model. Get whatever you can started so that you have a place to land. Having my coaching cert, meant I could take corporate coaching gigs right away. But if you are waiting for a nice easy, plush left turn…it’s called being independently wealthy. Anything short of that be prepared for the thrill ride of cutting across traffic to your new life.  

5) You just got a promotion to VP of Sales

I knew I would have to do business development. Meet with others. Tell people what I do now. But WOW, I underestimated that I am now in sales full-time. My first mentor Jamie Clay told me, “Sales is the transfer of emotion to get someone to take action.”  Be so crisp on the problem you are passionate about solving that you transfer that emotion to others. Have excellent marketing materials that transfer that emotion. Have a tight way of talking about your offerings. If you meander around, you won’t close the sale. “But Reagan I don’t like sales.” Cool! Don’t be an entrepreneur. It requires you to do marketing and sales of yourself. Most importantly, you must have a strong network to engage in effective sales. I loved the advice I got from Brand Builders Group, “Don’t ask your network for a job, ask them for a referral.” That is a great way for someone you trust to refer you to someone who is a fit for your solution.   

Tip: Have a mindset that you are your best advertising for what you do and how you can help others. Make sure you can talk about it succinctly. Spend a lot of time up front on the problem your customer has. Create your offering. Determine your pricing. Invest in your marketing. Of course, these things will change and evolve but having that focus is critical. Meet with people. Ask how you can help them. Understand their real challenges. It is amazing how investing in others somehow comes back around to you. 

6) Don’t try and do it yourself.

I would not have been even this successful without help. I found an assistant for 5 hours a week to take the low hanging fruit off my plate that I suck at and don’t enjoy. I found incredible partners like my executive producer of my sizzle reel and my branding expert to create my brand and my press kit. Think of them as your team. Your partners. Listen to them. I also have a huge community of people who are trying to do this speaking thing. We encourage each other. Cheer each other on.  

Tip: If you have spent any time in a workplace, you are used to having a team. So, build one around you as a business owner.  Seek our partners and communities where you can get help and give help. Invest in relationships so you can fight the huge isolation that comes with solopreneurship.  

7) You may work longer hours and have less control.

There is this very strange phrase everyone keeps saying to me, “isn’t it great to be your own boss? Control your own schedule? Do what YOU want to do?” Ummm. Kinda. I mean it is great. But dude, you are it. I have worked longer hours as a business owner (aka. One woman band) than I did as a corporate exec. Plus, I don’t own my schedule, my clients do. If they want to meet on Sunday. I have to meet on Sunday. If they want me to travel. I have to travel. NOW that won’t last forever. You can have boundaries. You can guide them over time into a schedule you want. All of this happens as the business matures but Mai Tai’s at 2PM isn’t a reality at first.  

Tip: At first, be prepared to have longer hours and less control. Think about hard yes and no’s to how and when you will and then be flexible to meet the needs of your business and customers. Guide them over time to the state you want. Be prepared if you say no (totally fine) it might me you lose an opportunity and that might be ok. I am starting to say no or dictate terms as I learn more about my new boundaries.  

8) Focus on impact.

As a recovering corporate lady I love numbers. Quarterly sales reports. YEAH! Budget forecasting. HECK YEAH! So, it was natural for me to want to focus on top line revenue, clicks on my website, or views of my TEDx talk as a measuring stick of my success. But I am much more satisfied and successful when I actually change people’s lives. So, I ask myself two questions every day, “Who can I impact today? What can I learn?’  

Tip: Focus on how you can help others as your best business strategy. Adding value. Making an impact. Unleashing someone else’s potential. All of that is how you build your client base.   

Reagan’s Rule: When I focus on revenue, I get anxious. When I focus on impact, I get revenue. Have the focus daily be on how you can help others. 

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