The term “entrepreneurial spirit” has become a bit cliché so I will say that I have always followed my own beat, been insanely impatient and enjoyed building things on my own. Whether it’s painting my apartment from 7 PM-4:30 AM because I saw the “perfect color” on the pages of Vogue or learning to build a website because I wasn’t getting hired at Conde fast enough, I have never been afraid of diving in and working to figure something out.
It has also never occurred to me that I would not do work that I loved and was passionate about. Maybe it would not always make me a living (and it hasn’t) but that was never a reason to stop building and trying. In fact, those were the times I did my best work and it often led to something bigger.
If you’re working on your side hustle, in the midst of a launch or giving it your all every day in your start-up, you know that the life of an entrepreneur can be complex; exciting one minute and terrifying the next.
So whether you’re just starting your journey or well into it, I am sharing 30 lessons I had to learn the hard way in the hopes that you won’t have to.
1. Surround yourself with people who celebrate and challenge you. I work very hard at a full-time job and a full-time consulting career which means my downtime and social life are places where I want to feel relaxed and happy. Spending your time with people who drag you down either with their attitude or behavior is only going to suck your energy — energy you will have to take time to replenish later.
2. Curating a life and career you love cannot happen if you say “yes” to everything. While you may want to attend every party and meet every new person for coffee, the fact is you’re going to have to prioritize a few things and people each week and be OK with letting others down.
3. You have to be ruthless in protecting your right to evolve. There are plenty of people who will support your growth and plenty who won’t and neither of them should have any control on your choices. You’re allowed to change your mind, hairstyle, goals, dreams, outlook or anything else you deem fit, whenever you want to.
4. If you choose to have a partner, choose wisely. No one really talks about the fact that partner choice is one of the most important decisions you will ever make. This is the person who will either bring you soup when you’re sick or leave you alone to fend for yourself. Will this person make you laugh when you’re down or tell you to suck it up? Will they support you when you need to work through a weekend to make an important deadline or give you sh*t about it? Your personal happiness greatly shrinks and expands in accordance with the type of person you choose to make your VIP.
5. Just because your life has been hard doesn’t mean you can never be happy. But the only way you will be happy is if you let go of what was hard.
6. Everyone makes mistakes. That’s called growing.
7. People are going to ask you a lot of questions and it’s not your job to answer them all. It’s OK if you don’t know whether or not you want to get married when you’re wedding date is if you are engaged, what you’re USP is for your new business idea is. If you’re doing what you need to do to get clarity in your own life about your own stuff, you’re doing fine.
10. There are some days that just have to be written off as classic sh*tty days, and when you have them, it’s OK to wallow. But do it in style. Pour some wine, throw on some Otis Redding or Patsy Cline and get really into it. Then hop into a bath, throw on a mask and go to bed so you can get up and kick ass the next day.
11. If you want a good life, a successful relationship and a thriving career, you’ll need to have a good attitude. No one wants to be around someone with a lousy demeanor.
12. No matter how hard you work at it, you’ll never be happy 100% of the time. But if you’re miserable 100% of the time, you’re working at it like a full-time job.
13. It’s one thing to know that life is not fair, but don’t forget that people aren’t always fair. You don’t need to be cynical but pay attention to the promises that are made, who has their hands out and when and when your gut burns, move on.
15. Not every client is right for you. I learned this from my former boss and (and adopted dad), Preston Bailey. It’s always exciting to get a client in the beginning and everyone needs money, but after you have worked with a client who doesn’t share your values or vision, you quickly learn to be selective.
16. Don’t be afraid to walk away from what’s not right for you and always walk away when someone gives you an ultimatum.
17. Your home should be your sanctuary and your home office should be a high vibe creative space. They can be under the same roof but they should remain in separate areas.
18. If you work from home, get out into the city. I’ll be there are loads of workspaces all over your city that you don’t even know about (I love working at Aragon House in Parsons Green and Blue Bird in Chelsea) and it helps to get out of your comfort zone around others, even if not interacting. This can also help to improve your relationships with others. My fiance once said, “The issue with one person working from home and the other not is that the person outside of the office coming home might be the first human interaction the one at home has had, but they forget they are not the first interaction the one in the office has had. One is ready to talk and the other just wants to unwind.”
19. Don’t get caught up on trying to make people recognize your value. Most people are able to see how valuable you are, they just don’t acknowledge it to test how well you recognize it.
20. Collaboration and partnerships are professional relationships. Make sure that your values are aligned, your brands are compatible and your vision for the future in-sync before you sign on to go public as a pair.
21. Busy isn’t the same as productive and burnout is not a badge of honor.
22. Wake up every day and commit to doing one new thing, one thing great and one thing to make your brand just a little bit better. Do this for 30 days and you’ll be further than most people get in 6 months.
23. Always say thank you. It’s nice in a card, an email and a text, better in a phone call and best in person.
24. Write down your daily wins. Going over these will help you when the hard days come around.
25. Do whatever you need to do to get on your own side. Meditate, journal, go to therapy, do it all. Just find a way to become your own best friend. As Lucille Ball once said, “Love yourself first and everything else falls into line. You really have to love yourself to get anything done in this world.
25. You don’t need to argue with every idiot or prove every point. If your own personal happiness or success is not invested in the argument and no one is getting hurt by it, laugh it off and move on with your life.
26. Prepare the best you can in every way you can. Risk is a word we use flippantly but it really means “exposure to loss and danger”. The more you know, the less likely it is you will lose and the less dangerous situations will seem. Preparation turns risky situations into powerful opportunities.
27. Comparing yourself to others is a game played by people with too little ambition.
28. Be as kind and helpful as you can with every person you meet. Leave a trail of smiles, inspiration and hope and you will find that the world is a more open and welcoming place as time goes on. It’s not about being inauthentic, but about respecting people, acknowledging their gifts and understanding that there is room for all of us.
29. Figure out how to carry a good conversation and how to elevate one. Keep up on world events, show some interest in the lives of others and avoid school kid chat (gossip, silly put-downs to get a laugh, close-minded comments and so on). Think of the person you admire most and imagine they are in the conversation with you and whatever party is actually there. This will do wonders for you at networking events and dinner parties.
30. Finally, keep going. Keep dreaming and working, fighting and resting when you need to. If you’re doing the best you can to do what you love, you’ve already won.
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