in entrepreneurship

Doing the Work vs. Letting Go

Confession: I work a lot. Probably too much. The first step up recognizing you have a problem is admitting you have a problem, right?

And while having too much on your plate is better than wondering if you’ll be able to pay the bills each month, it’s still very much a problem.

After a year of being an entrepreneur, I still have one big obstacle to overcome: Knowing when to let go. Accepting the fact that I can’t do it all, but more importantly, I don’t need to. It’s true what they say – one man’s passion is another man’s obsession, and there’s a thin line between working hard and over-working.

Some prefer to do all the labor themselves, while others would rather outsource everything. At the end of the day, it’s finding a balance, determining what works best for you so you CAN focus on doing meaningful work that you 1) are good at and 2) want to be doing.

Here are a few ways I’m working to become less overwhelmed and more focused as an entrepreneur:

Trust other people

My wife tells me I’m working too hard, my business partner tells me I’m working too much, my own body tells me I’m over-worked. For a long time I ignored all of the symptoms of being a workaholic, telling myself that you had to work a ton to get anywhere. And while starting a business is without a doubt hard work and long hours, I don’t (and you don’t) want to fall into the trap of working too much and neglecting the other things that matter most.

Listen to yourself, and listen to the other people you trust who have your best interest in mind. It’s not always easy, but you’ll be glad you did.

Helping others helps yourself

Outsourcing often is associated with being a “dirty” word – I’m not sure why, but as a solo-preneur turned entrepreneur who works with other people every day, it was and still is difficult for me to hand off work that I could do myself to someone else (often times to someone who can do it much better).

I think it’s like having a kid, being with them every day, and then sending them off to daycare for the first time (I’m not a parent so I’m not the expert here). You develop an attachment to your work and it’s difficult to let that go and trust someone, anyone else.

But in order to take on more work and grow as a business, you have to involve others and trust on the ability of other people. Aside from that, by outsourcing and involving other entrepreneurs and freelancers, you’re helping them pursue their passions and do work that they love. Focusing on what you’re best at and involving others to handle what their best at is a win-win for everyone. Focused work = good work.

Money matters: Manage your finances

I’ve said it here many times before, and whether you keep a spreadsheet or write things down on a whiteboard, money, and figuring out 1) how much you need and 2) how much you’d like to have, is critical to success. Any business-owner who tells you making money is a non-issue is full of shit. So, since money is important and necessary for survival, it’s obviously important to know, at the very least, how much you need.

The quickest way to start working less is by knowing you’re financially secure enough to do so. If you’ve made what you need to make for the month, the quarter, or however you decide to benchmark, any jobs that come in beyond that point can be handled by someone else, if you let them.

Try it out this month or next – once you’ve made what you need for the month, send the next project to someone else who’s capable and hungry to take on the project – transition yourself from labor-worker to manager. The transition doesn’t have to happen all at once, but little by little, you’ll reduce your workload and (ideally) learn that you’re still more than comfortable financially even when you’re not doing 100% of the labor.

Define your work day and set expectations

Whether it’s deciding when you are (and are not) going to respond to emails, or setting a limit to the number of clients you’ll take on each month – set some expectations for yourself, and stick to them.

I used to answer emails from 5am until 11pm, with no real “work hours”. This is fine for a while, but eventually your clients will come to expect that you’ll answer their emails all hours of the day, and when you don’t, they wonder what the hell happened to you. If you’re at this point, you’ve crossed the dangerous threshold of making yourself TOO available to your clients. Define your work day and set realistic expectations that you can live up to.

These are just a few things I’m doing as I continue to develop into doing more work “on the business” and less “in the business” – these are areas I believe are necessary to accept and embrace in order to succeed and thrive as an entrepreneur.

What are you doing to “let go” and focus on the work you want to be doing? What advice would you give to other entrepreneurs out there?

(Photo c/o robinrowell)

Add Your Voice


  1. I’m not an entrepreneur. But there is enough work at my job where I could work until 7 or 8 every night. Easy.

    So in order to prevent burnout, I make sure to leave my work at the office (unless an emergency pops up.) If I tell myself I am leaving at 5:30, I make sure the important work is done.

    I would suggest that entrepreneurs do the same. Set a time when you are done working, and stick to it. Maybe leave your house (or wherever you work) and go somewhere so you get that same feeling of leaving work. I don’t know. I’m sure it’s quite different than working for a company.

    Also – I agree with your statement about setting e-mail expectations. Once somebody sees you responding to mail at 10:30 p.m., they assume you’re always available at that time. It can be a tough trend to reverse.

    • One of the biggest challenges I face is that I work from home. I wrote about it a few weeks ago – that one of the most difficult things about being an entrepreneur is the freedom that comes with it, being able to work from home, sit on the couch with my laptop with the TV on. When you go into an office each day, it’s easier to separate career life and personal life. Working from home presents a huge challenge because those two worlds blur very easily.

      It’s all about setting boundaries and defining your work schedule and work environment.

      Thanks for the comment, Brad!

  2. I really can’t believe that you posted this today – it’s totally what I needed to read! I’m teaching full-time while trying to study/launch a dog training career (eventually to replace teaching), while attempting to maintain all of my current freelance writing commitments (oh and staying in shape and spending some time with my boyfriend in there too). Maybe it is time to cut some things loose…

    • I’m glad it hit home, Abbie! Prioritization and organization seems like a no-brainer, but it’s one of the most difficult challenges we face. Best of luck figuring out what matters most and what to put your energy toward…

  3. Hmm… The phrase that comes to mind is ‘Get a life’… :-)

    It’s about integrating work with your life so the other part takes on an equal importance. Your relationship should be the most important thing, listen to your partner. (He says while working on a Sunday…)

  4. You know what Matt I agree entirely. I just went off line for a full 5 days hiking in Patagonia. There was no way I could or wanted to access wifi and I prayed and hoped that the little bit of work I outsource would get done and that things would hold up in my business.

    What I realised when I got back was that all had been done, things were going well and that I should go away more often. I also realised how amazing nature is and that I want to be doing anything that involves getting outdoors more and enjoying life and that does not involve working all hours. In fact I didn’t even want to turn on my laptop so I KNOW that things are going to change for me. I’m all about living life as an adventure and having fun while working.