Never Give Up. Never Surrender.

How many times do you try to solve something before you give up? Once? Twice? Never?

Perhaps you have something you want or that you need to accomplish and, while there may be alternatives, they aren’t what you ideally want to do. Sometimes, it’s easier to go with the path of least resistance and accept a less-than-perfect solution. And sometimes, maybe you realize what you want isn’t really what you should be going after and it takes perspective to be able to recognize that and change course. But many times, I see people giving up far too easily on something they should never give up on.

Last year, I took on a project that ended up requiring me to do something I’d never done before and therefore had no experience with. However, the project didn’t start out that way – the original goals were all pretty familiar stuff but, as we got further into things, my client realized that they needed to expand the scope and that pushed us into this new territory for me. So the question was what to do.

Ultimately, I looked at the project at its entirety and recognized that this new piece, while not insignificant, was still a relatively small component and that I felt confident I could handle everything else. Still, I wanted to make sure things were done well so I decided to find a knowledgeable resource – a developer in this case – that I could subcontract this one part out to. And for a variety of reasons, I opted to not go back and ask for more money to do this extra piece (more on that later). So I was going to eat the cost.

I have a developed a pretty good sense over the years as to whether what I’m trying to do is possible and I had this strong feeling that I could pull this off. What’s more, I had ideas on how to do this for a very reasonable cost so I started exploring options.

Several were crossed off the list pretty quickly but one that I had a good feeling about was to look at some of the freelancer sites that are out there. If you’re not familiar with them, you post details of the work you want done and freelancers and agencies can send you proposals, or you can search for and invite talent to apply to the job. I posted my project before going to bed that night and, by the next morning, I had 8 proposals from people all over the world. And to my delight, the hourly rates a lot of them were charging was maybe 10% – 25% of what I was expecting.

But then I started running into complications.

Pretty quickly, I identified my top two choices but, despite their initial quick response, both went silent when I sent follow up questions. After waiting a day, I decided to take action and went proactively searching for resources. I turned up three freelancers whose expertise lined up very nicely with my projects so I sent messages to all of them inviting them to review my proposal. I was saved!

Until I wasn’t.

All three ended up passing for various reasons – too busy, not interested in the work or, in one case, another silent treatment. However, one of the first two people finally responded at the same time so I was hopeful – until I read her response and saw that she ignored my questions entirely and essentially said “trust me, I can do this.” While I appreciated her self-confidence, she failed to get my buy in. What’s worse – we were not three days in and I was closer to a solution so I came up with a Plan C.

I opened an account on a competing freelancer site, searched and found two strong resources there. I started trading notes with both and one of the developers who responded seemed both knowledgeable and interested in the work. Again, I start thinking I had my answer, especially when he said he’d work up a proposal and get right back to me. Well, my project’s been done for four months now and I still am waiting for that proposal

So, onwards to Plan D. I went back to the original freelancer site as it had better search filters but I decided to change up who I was searching for. I rethought my requirements and, to my surprise, found three more freelancers who looked like they could do the work. So I reached out to all three; two quickly responded and one ended up being very aligned with what I was hoping to do. Even better, his communications were quick and on-point. And the best news? His rate was roughly half of what my first choice wanted to charge. So I hired him and – despite a couple of further bumps in the road – it all worked out well.

I realize this little story isn’t high drama or frankly all that interesting, but I share these details to illustrate a pattern we all run into:

A challenge arises > Solution #1 > That didn’t work > On to idea #2 > That doesn’t work > OK, idea #3 > … and so on.

At some point, it is understandable if someone says “enough.” How many times do I need to run into a brick wall before I finally give up, after all? But that’s not the intent of my message here.

Yes, if you keep doing the same thing, or very similar things, and keep ending up failing, you probably need to change up more things in your approach. In my case, I stayed close to the idea of hiring a freelancer but who I went after, how I found them and where I looked all changed with each pass. And while my Plan D ultimately worked, I had also started to stub out Plans E & F in my head, with each one being more-and-more “radical” (E was going to see me going to some local universities to see if I could hire a student for the job, while F would mean hiring a more traditional development company and going back to the client to help fund it).

Still, setting my specifics aside, it’s the pattern here that I’m trying to highlight. If you really want something… if it is ultimately worth pursuing… if you can still see possible ways forward, then don’t ever give up.

Being tenacious in pursuit of something you want can be a really good thing. You can be the person who ultimately pulls out the win where others have thrown in the towel. My only caution is that there always needs to be a balance of the effort vs. the potential reward. For my project, my hope was that delivering everything the client asked for – and maybe a bit more – would result in a contract extension. And, thankfully, that’s exactly what came to pass so the extra time and effort I’d invested definitely had a longer-term benefit. While that wasn’t a guarantee, it seemed a good possibility and it ultimately paid off.

Ironically, I had the very opposite outcome several years ago when my wife and I went to buy a car. We were in love with this one particular model and, honestly, were probably a little too obsessed with it. Thankfully, we were going to buy used which was going to save us some money but it also meant there were fewer cars on the market to choose from as it was only a couple of years old. Still, we persisted and, despite several failures, we eventually found the perfect car. Or so we thought.

The funny thing is that this one felt like we were forcing our will on the universe. It was almost as if something didn’t want us to buy the car. One got sold out from under us while we were talking with the dealership; a bank misplaced our loan application so we lost out on a second one; and so it went until we finally purchased our car from a private seller. Looking back, I wish I hadn’t been so persistent as that car turned out to be a lemon and we sunk thousands of dollars in repairs before we finally gave up and sold it 18 months later.

The bottom line to all of this is that there are almost always solutions to be found and you can set yourself apart by being willing to keep after finding them. Still, the solution you come up with may not always be practical or affordable so you need to balance your efforts against an objective assessment of what you should do and then commit your efforts content in the knowledge that you’re doing what you think is right.

Know that I’m pulling for you.