10 Clues That It May Be Time to Seek Outside Help

If an entrepreneur doesn’t find themselves in over their head at least 20% of the time, they are probably not pushing the limits, not taking enough risk, and probably not working on an idea that’s worth doing. The challenge in to know when and how to ask for help, and not let bravado and ego mask anxieties. The best people know when they don’t know, and know how to find the right help.

Unfortunately, too many entrepreneurs I know are terrible at finding and accepting help. Perhaps it’s because they jumped into this lifestyle because they are passionate and stubborn about following their own vision, and they enjoy being their own boss. Too often they are also hesitant, inexperienced, and fearful of hiring people or finding a mentor to be the partner they need.

In the spirit of mentoring and helping entrepreneurs recognize their own weaknesses, here are ten key indications from my experience that you as an entrepreneur may be in over your head, and it’s time to look for some help:

1. You start seeing every business problem as a personal affront.Your business is not all about what is best for you, but what is best for your customers. In reality, your customers care more about your product and service, so feedback on product shortcomings or service glitches are meant to help your business, not hurt you.
2. Startup challenges become more depressing than energizing. The best entrepreneurs thrive on being able to push the limits, and tackling the tough challenges that ultimately result in real innovation which can change the world. If you find yourself dragging in to work, and dreading the next surprise, you may be in over your head.
3. You have no idea how to pivot with the latest market trends. Successful entrepreneurs pride themselves on always having more ideas than can possibly be explored, so they are never at a loss for new alternatives to explore. If you don’t see a new trend as a new opportunity, you may be in over your head. Seek help or get out.
4. You are completely surprised by a negative event you should have foreseen. At the end of a given month, you suddenly are totally out of cash. You know you should have been tracking the burn rate, or inventory requirements, or late receivables, but have found yourself totally distracted by a flock of emergency daily issues.
5. You know what is required, but you continue to procrastinate. Sometimes it’s obvious that closing a deal requires some tough negotiation or sales calls at the top, but these are not your forte, so you can never find the time or energy to get them done. Maybe it’s time to find an advisor, or a board member with the right connections.
6. Angry outbursts become more common than real leadership. Too many executives revert to bullying and micromanaging when they are in over their heads. In the long run, this tactic does not work, and your business suffers, as well as all those around you. If you catch yourself acting out in anger, get some help before more damage is done.
7. You start playing the blame game. We all know entrepreneurs that are quick with an excuse for every problem, like we were too early for the market, the vendor let me down, the economy took a downturn, or my competitor is cutthroat. Every startup founder has to remember that the buck stops with them, and they must learn from every mistake.
8. Living in a state of denial, and misrepresenting the truth. When an entrepreneur is in over their head, they can’t face the hard facts of business losses and missed customer commitments, and they can’t face their team. Thus they find themselves communicating less and less, and downright lying to people, while rationalizing that this causes less pain.
9. Jeopardizing your integrity to hide shortcomings. If you catch yourself saying things and doing things that violate your own sense of ethics, you are likely in over your head. These could include cutting quality corners, shorting vendor payments, and sabotaging team members. Now is the time to get help before you destroy yourself and your startup.
10. Letting a sense of entitlement show through. It’s easy for an entrepreneur in over his head, and frustrated with all the challenges, to convince themselves that they are entitled to that fancy sports car or a six-figure salary once the first investor money rolls in. They let the burn rate go up too fast, and the business burns down before it really starts.

As a serious entrepreneur, you need to differentiate these symptoms from the plateaus we all feel from time to time as we jump from one learning curve to the next. In most cases, if you focus for a couple of months, you will find yourself happily afloat at the new level. That is just getting in over your head in a healthy way, rather than an unhealthy one.

According to Whitney Johnson in an old Harvard Business Review article on this subject, the smart recovery is to send out an SOS (stop, organize, secure) before you drown, when you find yourself really in over your head. As an entrepreneur, you are expected to swim in unexplored waters, so there is no shame in accepting life preservers, as long as you learn from the waves.

So remember, none of us is perfect, and almost no entrepreneur gets it right the first time. If you never make mistakes, you are not taking enough risk to win in today’s market. But always be self-aware, and not be afraid to take a hard look in the mirror. Do you like what you see, and are you willing to change it?