6 Things Every Entrepreneur Struggles With, but No One Admits

March 24, 2015

Connect Member

Wealth Mastery Coach, championing women overachievers to reclaim your freedom, travel and play!


Over time, I’ve noticed a pattern with the overachieving women entrepreneurs I coach or mentor: They all want to know about the mistakes I’ve made.

For the longest time, I couldn’t figure out why they were interested in my struggles. How could my failures help them? But I’ve realized that in today’s world of social media — where our Facebook news feeds are filled with happy news of engagements, vacations, speaking gigs, and babies — learning about my mistakes and failures gives clients the reassurance that they too can succeed and that they too can be human.

I’ll publically name what’s not being said: six major struggles entrepreneurs face, but are often too embarrassed to admit (especially on Facebook).

1. The Desire to Struggle
So many of us are programmed to struggle. We think that we’ll get a trophy for working harder and faster. We think we’ll get a blue ribbon if we’re busier and more burnt out than anyone else. My parents are immigrants, and we were always outsiders; our whole lives we heard stories of my grandparents fleeing communism and walking 10,000 miles to go to school. It’s like we’re pre-programmed to survive, not thrive — hence this unconscious drive to work like a horse, rather than savor the present.

My coach helped me break that addiction to struggle with one question: What’s your capacity for joy? I answered with, “Oh! I can handle tremendous pain.” She laughed. I went on a rant about how I can handle the weight of the world: every injustice, every heartbreak, every violation, every obligation — you name it, I’ve suffered it. She interrupted my rant, “I didn’t ask about pain. I asked about your capacity for joy?” I went blank. I didn’t have one! My ego (survival brain) fooled me into believing I had to struggle. Talk about a major breakthrough.

2. Comparison-itis
A bad case of “comparison-itis” flared up when I didn’t make it onto the “30 Under 30” list. At 21, I was so sure I would make it. I had potential. I had smarts. I had everything it takes to be a global leader. Now, in my early 30s, I feel like a mega-failure for not making that list. I also have idols who have published 11 New York Times bestsellers, which triggers my inner voice saying, “Oh, shit! I’m 11 books behind.” I much later discovered that it was because the universe had other lessons for me to learn first: how to recover from disastrous heartbreak, how to recover from a health burnout, and how to love and care for myself first before I love and care for others. Sure, if I had skipped those important life lessons, I might have gotten on that list. But I might also be fat, divorced, and bankrupt. There is such a sense of acceptance in letting go of my own plan and acknowledging that there is a bigger plan out there for me.

3. Scarcity Inheritance
Many of us inherited a money-doesn’t-grow-on-trees, there’s-not-enough-to-go-around mentality. A practical example in my life: I live in Canada, about an hour and a half from the U.S. border. Early on, I would drive three hours round-trip to my P.O. Box in the States to pick up a shipment from Amazon.com, instead of ordering directly from Amazon.ca — all that just to save $40. I was so entrenched in this mentality that I thought, “Score! I saved $40 and my P.O. Box only cost $12 per year.” Except, I didn’t factor in gas and the value of my time. It seems completely ridiculous to me. But I was so stuck in that scarcity mindset that it caused me to behave and make decisions that were not financially powerful

4. Unmonetized Talent
In all of my business roles, I’ve been hired by clients for my talent for monetizing everything. I helped them streamline their systems — monetize, monetize, monetize. Although I saved a client organization $1.2 million, that mindset came at a cost for me: I picked deadlines and milestones over people. I put tasks before relationships. I was awakened by this upside down approach to success when a mentor said, “Your net worth is intimately related to your network.” And that turned my world right side up. Just as we should dance like no one’s watching, I started blogging like no one’s reading. And even though it felt so uncomfortable to not monetize this talent, this daily practice led to even bigger networks, even better relationships, and eventually even more money. It feels counterintuitive and yet so profound!

5. Impatience With the Universe
A funny story: I went to see an energy healer, and she told me that our souls come back on Earth with many roles and purposes. She told me that I had fulfilled all my purposes, I’ve paid my dues, and my soul is so highly evolved that it gets to choose if it comes back into mortal form or not. I thought, “Sweet! I’m done!” And then I got really philosophical and wondered, “If I’m done, if my soul is so highly evolved, then why aren’t I a multibillionaire? What gives?” After much huffing and puffing and thinking, I came to the conclusion that in this lifetime, I am still learning to be satisfied with the present moment, in every moment. Check me out, I’ve already skipped ahead to deciding what my next soul will do!

6. Irritation With Prospective Clients
When my prospective clients are interested, but just not sure if they want to go through with a coaching program, I get really irritated. I want everyone to hold herself to a high bar, to a rich life, to leaping boldly forward for what their heart desires. Once, someone came along and said she wanted financial freedom, but she spent all her savings on a ski vacation. I couldn’t wrap my head around it. I would rather die than spend money I don’t have! Another time, a woman told me she’d do anything to help her parents retire — they have worked six jobs between the two of them. A few days later, she flaked. And that’s why they never become my clients. It’s frustrating to watch people throw away their worth, their dreams, and especially their freedom! My only comfort is knowing that it may not be the right time for them, or I’m not the right match for them. And my only wish is that they don’t wait until it hurts so badly that they HAVE to make a change.  

The bottom line is, we all have struggles. So how do we counter these issues and grow in spite of them? I like to use this Post-It exercise that has worked miracles for my clients: Take 100 sticky notes, put a check mark on each one, and then write something you’re proud of that you’ve already accomplished. Invite your friends and family for a “gallery viewing” of your Post-It wall — this is the part that usually makes my clients sweat profusely. It’s hard to brag about yourself! But doing this exercise can really help you celebrate your successes, acknowledge yourself for who you already are, and help you realize that you’ve already arrived.

Tina Chen is a member of the DailyWorth Connect program. Read more about the program here.